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Italy Villa rentals

Rentavilla.com provides a large selection of Villa rentals in Italy, Tuscany villas, Lakes, villa, Umbria villas, amalfi coast villa rentals from budget to luxury villas.


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Villa Bellissima Estate

Buonconvento

Sleeps 44
Baths 22
Week starting at € 105,385

Villa Bellissima VI is a destination like no other, combining the beauty and history of Tuscany in a tranquil setting where people from all over the ...more

Sublime Siena 2

Colle di Val D Elsa Siena

Sleeps 35
Baths 18
Week starting at € 40,385

Sublime Siena 2 is situated in the heart of the Tuscany countryside, between Siena and Florence, and is the ideal accommodation for anybody who loves ...more

Maremma Estate

Cecina

Sleeps 32
Baths 16
Week starting at € 22,185

Maremma Estate is a stunning, 32 acre (13 hectares) estate located in ancient, Etruscan country, on the borderland of northern Maremma, and four ...more

Villa Tocchi

Monticiano

Sleeps 27
Baths 14
Week starting at € 24,658

Villa Tocchi is located in the valleys of the Merse River, in the south of the province of Siena, not far from Montalcino and Pienza. You're not ...more

Villa Cispius

Lucca

Sleeps 25
Baths 12
Week starting at € 33,923

Villa Cispius is a grand Tuscan estate that has been completely restored to its former glory. Situated on a hill overlooking the valley below and ...more

Sublime Siena

Colle di Val D Elsa

Sleeps 25
Baths 13
Week starting at € 32,077

Sublime Siena is situated in the heart of the Tuscany countryside, between Siena and Florence, and is the ideal accommodation for anybody who loves ...more

Lucca Estate - Villa Bernard

Lucca / Vorno

Sleeps 24
Baths 12
Week starting at € 34,615

35% off for all weeks booked between June 1st and August 31st, 2013
Villa Bernard is tucked away among the gently folding hills of Lucca, and affords its guests luxurious accommodations. Restored with impeccable ...more

Lucca Estate - Villa Pera

Lucca / Vorno

Sleeps 22
Baths 11
Week starting at € 34,615

35% off for all weeks booked between June 1st and August 31st, 2013
Villa Pera, an elegant 19th century luxury villa rental in Lucca with its own chapel, olive oil press and castle ruins, is set in a vast estate of ...more

Lucca Estate - Villa Classica

Lucca / Vorno

Sleeps 22
Baths 12
Week starting at € 30,769

35% off for all weeks booked between June 1st and August 31st, 2013
A fine Tuscan house with 12 bedrooms that sleeps up to 22 people, situated at the heart of an outstanding 16th-century estate. This villa is set in ...more

Villa Elegante

Lucca

Sleeps 22/24
Baths 10
Week starting at € 12,769

Villa Elegante is a large luxurious villa in Lucca that can accommodate up to 24 people in 1350 square meters of living space. The villa belonged to ...more

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Tuscany Estate - Villa Grand Duc

Bucine / Montebenichi

Sleeps 22
Baths 11
Week starting at € 8,923

Nestled in the rolling hills between the Chianti and Crete areas of Tuscany, Villa Grand Duc used to be a Medici's Castle, taken over in the 15th ...more

Santo Estate - Villa Opera

Siena / Vescovado di Murlo

Sleeps 22
Baths 7
Week starting at € 4,671

10% dicount for available weeks during the periods: September 28th to the 21st of December.
Villa Opera is truly a work of art. Located in the center of a large working estate where they still produce grains, it's a large and grand villa ...more

Castello San Savino

Monte San Savino

Sleeps 22
Baths 11
Week starting at € 9,692

20% discount on all 2013 weeks still available. Offer valid as of April 10, 2013
A long driveway, dramatically lined with centuries-old cypress trees, leads up to the impressive Castello San Savino. First built in the Middle ...more

Villa Lorenzo

Lucca / Vorno

Sleeps 22/30
Baths 11
Week starting at € 28,077

Villa Lorenzo is a very large, registered early nineteenth century frescoed villa designed by the famous Lucchese architect Lorenzo Nottolini, who ...more

Villa Ambrosia

Lucca

Sleeps 22
Baths 19
Week starting at € 8,838

Villa Ambrosia definitely delights the senses with its pleasing mixture of stunning scenery, fragrant gardens, and historical relevance. Set in a ...more

Tenuta Alba

Florence

Sleeps 22
Baths 8
Week starting at € 8,400

Tenuta Alba is the perfect starting point to explore Tuscany. Situated in the heart of Chianti, it is only a 20 minutes' drive from Florence, 40 ...more

Villa Sinalunga

Siena

Sleeps 22
Baths 7
Week starting at € 15,385

Villa Sinalunga is one of the most renowned villas in the heart of Tuscany. 12 secluded, hilltop acres of beautiful traditional Tuscan landscape with ...more

Tuscany Estate - Casa Leopold

Bucine / Montebenichi

Sleeps 21
Baths 7
Week starting at € 8,077

Nestled in the rolling hills and sweeping valleys between Chianti and Siena is Casa Leopold. Built by the Grand Duke of Tuscany in the 1700's, this ...more

The Italian Villa 1

Siena / San Giovanni dAsso, Tuscany TUS

Sleeps 21
Baths 8
Week starting at € 8,446

The Italian Villa 1 consists of two side-by-side villas in the charming Tuscan hilltown of San Giovanni d’Asso. The main house (The Italian Villa) ...more

Pieve Hamlet

Lucca

Sleeps 20
Baths 10
Week starting at € 8,308

Pieve Hamlet is located in the beautiful rolling hills just outside Lucca. From the villas there are stunning views of Lucca and Pisa nestled among ...more

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Villa Classico

Montecatini Terme

Sleeps 19
Baths 11
Week starting at € 3,664

Set amongst ancient olive trees and the dramatic scenery of the bucolic Tuscan landscape is the magnificent Villa Classico.This large villa for rent ...more

Blessed Occasion Villa

Lucca

Sleeps 18/21
Baths 9
Week starting at € 5,615

Blessed Occasion Villa was built in the 1600's as a convent, hugging the ridge above the La Freddana Valley. The peaceful setting among olive trees ...more

The Count Ceuli 1

Pisa / Cevoli

Sleeps 18/19
Baths 9
Week starting at € 4,923

The Count Ceuli 1 villa is just outside the village of Cevoli near Pisa in Tuscany. The owners just completed (in 2006) the renovation of the fourth ...more

Villa Cermalus

Lucca

Sleeps 18/20
Baths 8
Week starting at € 6,885

Villa Cermalus is a magnificent property nestled in the rolling Tuscan hills outside of Lucca. The villa is very old, dating back to the Longobard ...more

Villa Bellissima I

Buonconvento

Sleeps 18
Baths 9
Week starting at € 43,846

The foundation of Villa Bellissima I in the heart of Tuscany, dates back to the fourteenth century. Recent renovations have taken this historic ...more

Villa Chiana

Val di Chiana

Sleeps 18
Baths 8
Week starting at € 8,423

Nestled high in the hills between the Chiana and Arno valleys, Villa Chiana has been authentically restored to an exacting standard. Once home to ...more

Villa Piscina

Poggio a Caiano

Sleeps 17/20
Baths 5
Week starting at € 7,915


Villa Piscina is a lovely 17th century villa once owned by the powerful Medici family, possibly as a hunting lodge. Located in the heart of Tuscany, ...more

Villa Valdichiana

Valdichiana - Arezzo

Sleeps 17/20
Baths 9
Week starting at € 5,496

Villa Valdiciana is an old country residence, skillfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian ...more

Casa Segromigno

Lucca

Sleeps 16
Baths 5
Week starting at € 4,538

Casa Segromigno is a lovely old villa in the countryside just outside Lucca. It's been fully renovated with all the modern conveniences, including ...more

Villa Pienza

Pienza

Sleeps 16
Baths 7
Week starting at € 7,154

10% discount on the listed rates for all bookings made before April 15
Recently restored to the highest standard, this deluxe country house is in the beautiful Val D'Orcia in the South-Eastern part of the Siena province ...more

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Villa Marchese

Gambassi Terme

Sleeps 16
Baths 8
Week starting at € 5,121

The History of this large and impressive villa to rent near San Gimignano goes back as far as 970 AD. Villa Marchese which once belonged to the ...more

Villa la Contessa

Siena / Trequanda

Sleeps 16/20
Baths 8
Week starting at € 8,154

Villa "La Contessa" is a must for an unforgettable stay in the heart of Tuscany. Located 35 kms south of Siena in the "Crete", the building dates ...more

Abbazia - Casa Monte Cetona

Siena / Sarteano

Sleeps 16
Baths 8
Week starting at € 3,923

The large and lovely Casa Monte Cetona easily accommodates up to 16 people in an area of 5000 square feet. Perched on the bench of a hillside, the ...more

The Italian Villa

Siena / San Giovanni dAsso, Tuscany

Sleeps 15
Baths 6
Week starting at € 6,462

The Italian Villa is a splendid home inside the charming Tuscan hilltown of San Giovanni d’Asso. Situated near a medieval castle, the Italian Villa ...more

Villa Panzano

Panzano in Chianti

Sleeps 15/18
Baths 9
Week starting at € 4,962

Villa Panzano in Chianti, an immense traditional stone holiday villa rental, has been lovingly restored to offer a delightful place of rest and ...more

Villa Lucchese

Lucca

Sleeps 14
Baths 6
Week starting at € 10,923

Villa Lucchese is a fine and richly decorated XVIII Century luxury villa to rent set in peaceful surroundings amongst the hills near Lucca. There are ...more

Abbazia - Casa Etruria

Siena / Sarteano

Sleeps 14
Baths 7
Week starting at € 3,231

The villa can sleep a maximum of 14 guests in 7 bedrooms. It dominates a poetic spot overlooking a small lake between woods and rolling hills. The ...more

Santo Estate - Villa preciosa

Siena / Monteroni Arbia

Sleeps 14
Baths 5
Week starting at € 3,315

In the heart of the beautiful and enchanting Tuscan landscape lies a charmingly restored villa to rent with its very own patron saint; Saint Stefano. ...more

Villa Flora

Lucca

Sleeps 14
Baths 7
Week starting at € 6,077

Not far from the delightful and urbane town of Lucca, in a small charming village, lies a unique bit of local history. Surrounded by lush green ...more

The Hilltop Villa

Vicchio

Sleeps 14
Baths 6
Week starting at € 4,538

The Hilltop Villa is located just thirty five kilometers north of Florence in the Mugello region, also known as "The Switzerland of Tuscany". This ...more

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Casa Marlia

Lucca

Sleeps 14
Baths 7
Week starting at € 15,154

Super Discount: USD 8,500 per week instead of USD 19,700 for any week booked between now and May 31!!
Casa Marlia is the largest and most exquisite 16th century villa we can offer you. A noble house built in the popular symetrical architecture of the ...more

Abbazia - Casa Moiane

Siena / Sarteano

Sleeps 14/16
Baths 7
Week starting at € 3,615

The extraordinary Casa Moiane is a unique and lovely villa. It's 5700 square feet offer truly grand living for up to 16 guests. Overlooking the Val ...more

Villa Belle Vie

Bacchereto

Sleeps 14/16
Baths 7
Week starting at € 7,269

Villa Belle Vie truly does enable one to "live the good life". Located in the picturesque hills near Florence, the historical origins of this villa ...more

Abbazia - Casa Sarteano

Siena / Sarteano

Sleeps 14
Baths 7
Week starting at € 4,692

This villa can sleep 14 guests in 7 bedrooms. Built in stone it was home to a large family of 'Contadini', who worked the land for the monks of an ...more

Abbazia - Casa Arezzo

Siena / Sarteano

Sleeps 14/16
Baths 7
Week starting at € 3,615

This 7 bedroom Holiday rental in southern Tuscany sleeps 14 guests, plus an additional 2 guests with the use of two sofa/beds. Located the closest ...more

Abbazia - Casa Chiana

Siena / Sarteano

Sleeps 14/15
Baths 7
Week starting at € 3,615

This Toscana villa is 495 square meters and can sleep 14 guests in 7 rooms, or 15 guests with the use of a sofa/bed. The villa is set apart, ...more

Abbazia - Casa Crete

Siena / Sarteano

Sleeps 14
Baths 7
Week starting at € 3,615

The house is very comfortable and spacious with 7 bedrooms that can accommodate 14 people. The annex, with its large windows capturing the whole of ...more

Villa Chiara

Pienza

Sleeps 14
Baths 8
Week starting at € 5,400

Villa Chiara is a very exclusive villa in the Val D'orcia countryside, just three kilometers from Pienza. The villa sleeps up to 14 guests and is ...more

Villa Giuseppe

Subbiano - Arezzo

Sleeps 13/14
Baths 8
Week starting at € 2,438

Villa Giuseppe is the perfect place to discover the wonders of Tuscany and Umbria! This 7 bedroom villa is perfect for groups of 13 or 14 with 7 ...more

Villa Cypress

Montepulciano Tuscany

Sleeps 12/16
Baths 6
Week starting at € 4,692

Villa Cypress is a 6 bedroom historical villa in the countryside of Montepulciano, a vibrant city at the heart of the Siena region of Tuscany. The ...more

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Villa Patrizia

Lucca

Sleeps 12
Baths 5
Week starting at € 5,346

15% discount for all 2013 available weeks booked before May 31st
This charming vacation villa is located in the village of SS. Annunziata on the outskirts of Lucca. Villa Patrizia has sections dating to the 15th ...more

Casa Bravissima

S. Martino in Vignale - Lucca

Sleeps 12/14
Baths 5
Week starting at € 3,692

The city of Lucca attracts tourists from around the world to its historic sights. The Duomo Cathedral, St. Michael's Church and the streets and ...more

Villa La Citta

Pisa / Cevoli

Sleeps 12/14
Baths 5
Week starting at € 4,154

This lovely villa set in the Pisa countryside was built for a noble family from Pisa as their summer residence in the 19th century. It has a great ...more

Villa Brunello 1

Montalcino

Sleeps 12
Baths 6
Week starting at € 3,462

Villa Brunello 1 is as close to the universal dream of a perfect Tuscan country retreat as can be found! Set amongst a haven of natural tranquility ...more

Villa Bella

Chiusdino

Sleeps 12
Baths 5
Week starting at € 2,385

This great villa is set in the green historic countyside of Siena and perched upon the hill of Montesiepi. It lies between the Abbey of San Galgano ...more

Leopold Castle

Campiglia Marittima Livorno

Sleeps 12/26
Baths 13
Week starting at € 21,923

20% discount for all available weeks in June, July and August 2013
Built in the sixteenth century, Leopold Castle was the home of The Grand Duke of Tuscany "Leopold II" for many years. This Luxury Castle rental is a ...more

The Spanish Tower

Talamone

Sleeps 12
Baths 6
Week starting at € 11,538

The Spanish Tower, completely restored, is the ideal property to rent on the Tuscan Coast. Tucked away in a magical corner of Southern Tuscany, ...more

Villa in the Vines

Grosseto

Sleeps 12/15
Baths 6
Week starting at € 3,615

Villa in the vines sits atop fields upon fields of vineyards, just off to the west you can see the sea as the villa is near Grosetto in the coastal ...more

Villa Vorno

Lucca / Vorno

Sleeps 12
Baths 6
Week starting at € 19,191

Villa Vorno is a luxury villa, designed and furnished for the most discerning of visitors. Situated within easy walking of the picturesque village ...more

Villa Montevettolini

Montevettolini, Tuscany

Sleeps 12/14
Baths 6
Week starting at € 7,835

Set within a medieval borgo, Villa Montevettolini is certainly one of our most unique Tuscan holiday villa rentals. This remarkable villa has been ...more

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Villa Girasole

Lorenzana

Sleeps 12/15
Baths 5
Week starting at € 2,862

15% off the listed rates for all 2013 bookings
Villa Girasole is a classic Tuscan holiday rental estate near Pisa. Situated atop a gentle green hill surrounded by fields of wheat and sunflowers, ...more

Villa Pienza 1

Pienza

Sleeps 12
Baths 6
Week starting at € 4,692

Recently restored to the highest standard, this luxury villa rental is near Pienza in the beautiful Val D'Orcia in the South-Eastern part of the ...more

Villa Oppius

Argentario, Grosetto

Sleeps 12/13
Baths 7
Week starting at € 8,077

Villa Oppius is a magnificent villa set in Argentario, one of the most exclusive areas of the Tuscan coast. Perched 250 feet above the sea on a ...more

Il Toscona

Monteroni Arbia

Sleeps 12/14
Baths 6
Week starting at € 3,000

With spectacular views of the Tuscan landscape, Il Toscona is a newly restored independent villa with private swimming pool. The villa is spacious, ...more

Villa di Pietra

Forte dei Marmi

Sleeps 12
Baths 6
Week starting at € 8,369

Villa di Pietra is situated on the hills just behind Forte dei Marmi, only about 6 km away, with a sweeping panorama of the sea and the Versilia ...more

Villa Trevinano

San Casciano Dei Bagni

Sleeps 12
Baths 5
Week starting at € 2,754

Villa Trevinano sits in a unique location near the top of a hill, at around 580 meters above sea level, where Tuscany, Umbria and Lazio meet, ...more

Villa Rosina

Pienza

Sleeps 12
Baths 6
Week starting at € 2,700

Villa Rosina is an old, Tuscan country-style residence at the foot of Pienza that was recently restored into a beautiful six bedroom villa with ...more

La Tenuta

Siena / Asciano

Sleeps 11
Baths 6
Week starting at € 3,615

This country estate is composed of several buildings of historical and artistic importance, and the most beautiful is the main house with its ...more

Villa Chianti Rosa

Siena

Sleeps 11/12
Baths 6
Week starting at € 4,646

Villa Chianti Rosa is located in the heart of Chianti Senese, just 19 ​​km away from Siena and 55 Km from Florence. It is located in an ...more

Laura Estate

Vinci

Sleeps 10/13
Baths 4
Week starting at € 4,685

Deeply plunged in the typical Tuscan landscape, among olive trees and vineyards, Laura Estate is situated in the heart of a wide and relaxing park ...more

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Casa de Colori

Montecatini Alto, Tuscany, Italy

Sleeps 10
Baths 5
Week starting at € 3,462

This majestic villa rental overlooking the rolling hills of Tuscany between Lucca and Florence has the local village of Montecatini less than 100 ...more

Chianti Estate - Il Cipresso

Siena / Pianella Siena

Sleeps 10/12
Baths 4
Week starting at € 2,038

In the heart of the Chianti Classico region, this hillside estate offers a tranquil, classic Tuscan experience. Il Cipresso is a large house, ...more

Chianti Estate - Torrino

Siena / Pianella

Sleeps 10
Baths 4
Week starting at € 1,923

In the heart of the Chianti Classico region, this hillside estate offers a tranquil and classic Tuscan experience. Part of a small 17th century ...more

Chianti Estate - Scuola Piccola

Siena / Pianella

Sleeps 10
Baths 5
Week starting at € 3,692

This charming 17th century villa to rent near Siena in the Chianti was once a schoolhouse for a large estate, and has been restored as the private ...more

The Count Ceuli

Pisa / Cevoli

Sleeps 10
Baths 5
Week starting at € 3,731

The Count Ceuli villa is just outside the village of Cevoli in Tuscany. This large and noble three story villa was once a part of the country estate ...more

Villa Panorama

Siena / Asciano

Sleeps 10
Baths 5
Week starting at € 1,615

Villa Panorama is a traditional Tuscan country house rental situated in the beautiful area known as "Le Crete Senesi" south of Siena, with ...more

The Wishing Well Villa

Monticiano

Sleeps 10/12
Baths 3
Week starting at € 1,605

15% discount on the available weeks of May and June 2013
The Wishing Well is newly remodeled home located just outside the village of Monticiano which is 35 kilometers from Siena. This beautiful stone ...more

The Italian Home

Siena / Sovicile

Sleeps 10
Baths 3
Week starting at € 1,523

The Italian home is a large independent property that has been recently renovated with careful consideration to retain all the original ...more

Casa Mulino

Lucca / Vorno

Sleeps 10/14
Baths 6
Week starting at € 10,231

Casa Mulino is a large and beautiful Lucca villa that has its origin as the village mill. It has been beautifully restored to become a comfortable ...more

Villa San Giovanni

San Giovanni d'Asso

Sleeps 10/12
Baths 5
Week starting at € 4,846

In the beautiful Tuscan countryside of Val d'Orcia lays Villa San Giovanni, an ancient stone farmhouse that was completely refurbished in 2005. This ...more

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Casa Mercatale

Mercatale Val di Pesa

Sleeps 10/16
Baths 6
Week starting at € 7,231

Casa Mercatale has beautiful terracotta tiles and beamed ceilings. It has 530 sqm of living space divided into two floors and sleeps 10 guests in 5 ...more

Villa Seggiano

Seggiano

Sleeps 10/12
Baths 5
Week starting at € 1,458

Villa Seggiano is located just outside the peaceful country village of Seggiano. Situated in the rolling Tuscan hills, this special retreat offers ...more

Villa Bellissima V

Buonconvento

Sleeps 10
Baths 5
Week starting at € 25,000

Villa Bellissima V is one of 5 villas on the estate and can accommodate ten guests in it's spacious 5 bedroom suites. The foundation of Villa ...more

Palazzone Hideaway

Palazzone

Sleeps 10
Baths 4
Week starting at € 2,577

Palazzone Hideaway is a refined property located in Palazzone (Siena), about one and half hours from Rome and from Florence, and one hour away from ...more

Villa Oliva

Lucca

Sleeps 10/11
Baths 5
Week starting at € 4,215

This lovely villa is set up on the beautiful hills around Lucca, providing a great view of Lucca and the surrounding countryside. Villa Oliva is part ...more

Villa Arbia

Buonconvento

Sleeps 10
Baths 5
Week starting at € 2,900

Located in rich, agricultural countryside above the unspoiled valley of the Ombrone river, Villa Arbia commands an unrestricted pastoral view of ...more

Villa Arabella

Forte dei Marmi

Sleeps 10/11
Baths 6
Week starting at € 24,300

Villa Arabella is a lovely home located in Roma Imperiale, one of the best addresses in Forte dei Marmi. The owners have shown great care and ...more

Maremma Estate - Villa II

Cecina

Sleeps 10
Baths 5
Week starting at € 4,335

Maremma Estate is a stunning, 32 acre (13 hectares) estate located in ancient, Etruscan country, on the borderland of northern Maremma, and four ...more

Maremma Estate - Villa IV

Cecina

Sleeps 10
Baths 5
Week starting at € 4,858

Maremma Estate is a stunning, 32 acre (13 hectares) estate located in ancient, Etruscan country, on the borderland of northern Maremma, and four ...more

Villa Emmaline

Montepulciano

Sleeps 10/12
Baths 4
Week starting at € 3,377

Villa Emmaline is perched on a hill overlooking the beautiful Orcia Valley, a designated UNESCO World Heritage site. Just 10 minutes from Pienza, a ...more

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Villa Amiata

Casciano - Siena

Sleeps 10
Baths 5
Week starting at € 2,569

Situated in a quiet pastoral setting, and just to the south of Siena, stands Villa Amiata. Newly restored, and surrounded by almost 50 acres of ...more

Villa Ilario

Pienza

Sleeps 10
Baths 5
Week starting at € 2,131

Villa Ilario is an independent house with private swimming pool set amid the rolling countryside of Val d’Orcia, south of Siena. Val d’Orcia has been ...more

Villa la Torre

Certaldo

Sleeps 9/12
Baths 4
Week starting at € 4,154

20% discount for any week booked for the month of May 2013
This beautiful, spacious, traditional Italian vacation villa is set in a wonderfully quiet position halfway between Florence and Siena in the heart ...more

Villa Impressionato

Florence/Impruneta

Sleeps 9
Baths 5
Week starting at € 5,308

Villa Impressionato is a picturesque villa rental that sits on the main road from Impruneta to Martellina overlooking the hills toward Florence. The ...more

Pinewood Farmhouse

San Vincenzo / Piombino

Sleeps 9/11
Baths 3
Week starting at € 1,832

Pinewood Farmhouse is a large (400 square meter) villa rental on the Tuscan coast. It's surrounded by a fenced garden inside a vast wheat and ...more

Villa Torre

Siena

Sleeps 9
Baths 4
Week starting at € 1,750

Located in a wonderful position west of Siena, reached by a winding road through chestnut forests, stands the tiny hamlet of Villa Torre. On a grassy ...more

Villa Gemma

Lucca

Sleeps 9/10
Baths 3
Week starting at € 7,627

15% discount for all 2012 weeks available.
This magnificent villa is situated between Viareggio and Forte dei Marmi and ten minutes from the ancient walled city of Lucca. This elegant property ...more

Villa Levane

Arezzo - Levane

Sleeps 9/15
Baths 4
Week starting at € 3,446

Villa Levane is new to the market and recently restored for your comfort and enjoyment. Villa Levane is composed of a main villa with an annex. The ...more

Villa Lucente

Elba Island

Sleeps 8
Baths 4
Week starting at € 3,254

Villa Lucente is an attractive residence situated on two floors. This vacation villa to rent on Elba is the perfect place for those seeking absolute ...more

Chianti Estate - Il Cipressino

Siena / Pianella Siena

Sleeps 8
Baths 3
Week starting at € 1,731

In the heart of the Chianti Classico region, this large hillside working estate offers a tranquil, classic Tuscan experience. Il Cipresso is a ...more

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Chianti Estate -The Vineyard Villa

Siena / Pianella

Sleeps 8/9
Baths 3
Week starting at € 2,577

This beautiful villa is set in the heart of the Chianti region, offering a tranquil, classic Tuscan experience. The house is free-standing ...more

Piccolo Versailles

Lucca

Sleeps 8/10
Baths 6
Week starting at € 14,829

The incredible Piccolo Versailles is a one-of-a-kind property, in the category of palaces and grand chateaux. In fact it's valued by the Italian ...more

Bravo

Lucca

Sleeps 8/10
Baths 3
Week starting at € 2,462

The city of Lucca attracts tourists from around the world to its historic sights. The Duomo Cathedral, St. Michael's Church and the streets and ...more

Il Castello

Lucca / Montuolo

Sleeps 8
Baths 3
Week starting at € 2,471

The city of Lucca attracts tourists from around the world to its historic sights. The Duomo Cathedral, St. Michael's Church and the streets and ...more

Casa Lucca

Filettole - Lucca Lucca

Sleeps 8
Baths 2
Week starting at € 2,462

The city of Lucca, because of its rich history, attracts tourists from around the world. The three mile series of ramparts, complete with eleven ...more

Residence Michele

Lucca

Sleeps 8
Baths 3
Week starting at € 2,385

Residence Michele is actually half of Casa Segromigno, a lovely old villa in the countryside just outside Lucca. It's been fully renovated with all ...more

Residence Ada

Lucca

Sleeps 8
Baths 2
Week starting at € 2,385

Residence Ada is actually half of Casa Segromigno, a lovely old villa in the countryside just outside Lucca. It's been fully renovated with all the ...more

Villa Viareggio

Viareggio / Piano di Mommio

Sleeps 8/10
Baths 3
Week starting at € 2,692

Villa Viareggio has 4 bedrooms and sleeps 8 people. The villa is located in the plain, in a large and very well maintained garden. The area ...more

Lucca Estate - The Olive Delight

Lucca / Vorno

Sleeps 8
Baths 4
Week starting at € 9,846

The Olive Delight was originally an olive press and is still today surrounded by beautiful terraced olive groves. Its recent restoration has turned ...more

Villa Brunello

Montalcino Siena

Sleeps 8
Baths 4
Week starting at € 2,538

Villa Brunello is as close to the universal dream of a perfect Tuscan country retreat as can be found! Set amongst a haven of natural tranquility and ...more

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Villa Pastoral

Chiusdino

Sleeps 8/16
Baths 4
Week starting at € 1,923

Villa Pastoral is a beautiful and charming 17th century Tuscan stone home located at the entrance of a small hamlet set in one of the untouched areas ...more

Villa Antimo

Castelnuovo dell Abate

Sleeps 8
Baths 2
Week starting at € 2,923

Villa Antimo began life as a water mill in the 13th century. In 1606, the powerful Arrighi family enlarged the mill, which was fully functional ...more

La Castagnetta 1

San Gimignano / Il Castagno

Sleeps 8
Baths 4
Week starting at € 1,622

This estate is located on a hilltop and overlooks all the nearby valleys that extend as far as your eye can see. The History of this estate goes back ...more

La Castagnetta 3

San Gimignano / Il Castagno

Sleeps 8
Baths 3
Week starting at € 1,535

This estate is located on a hilltop and overlooks all the nearby valleys that extend as far as your eye can see. The History of this estate goes back ...more

Villa Terme

Gambassi Terme

Sleeps 8/9
Baths 3
Week starting at € 1,769

Villa Terme lives up to its name as there are breathtaking views of the rolling hills of Volterra and the Florentine countryside in all directions. A ...more

Abbazia - Villa Spineto

Siena / Sarteano

Sleeps 8/9
Baths 4
Week starting at € 2,538

Villa Spineto is a very old stone house that has been exquisitely updated to offer both privacy and a warm and welcoming atmosphere. The 2400 square ...more

Villa Raffaello

Pistoia Tuscany

Sleeps 8
Baths 3
Week starting at € 3,462

Villa Raffaello is a classic villa we discovered near Florence, only 1.5 km outside the charming town of Pistoia. Brand newly remodeled to high ...more

Villa San Gio

Montalcino

Sleeps 8
Baths 4
Week starting at € 4,346

As part of a large wine estate, this villa rental near Montalcino is in a private, peaceful and idyllic setting. Situated halfway up the hill of ...more

Villa Alhambra

Ambra

Sleeps 8
Baths 4
Week starting at € 4,154

This luxury villa is set in the beautiful hills of the heart of Tuscany, between Siena (25 Km) and Arezzo (35 km), on the Wine Route known as ...more

Casali Chianti

Panzano in Chianti

Sleeps 8/12
Baths 5
Week starting at € 4,481

Casali Chianti is an authentic farmhouse dating back to the 1600's with traditional decor and fabulous trompe d'oeil frescoed ceilings. The Casali ...more

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Villa Bellissima II

Buonconvento

Sleeps 8
Baths 4
Week starting at € 20,000

Villa Bellissima II once served as the chapel of the Villa Bellissima Estate. This villa is one of 5 villas on the estate and can accommodate eight ...more

Villa Francigena

Montemagno, Lucca

Sleeps 8
Baths 5
Week starting at € 3,865

Villa Francigena is located in a small hamlet called Montemagno which is near the famous walled town of Lucca. This 4 bedroom villa is perfect for 8 ...more

Villa Natalie

Lucca

Sleeps 8/9
Baths 4
Week starting at € 8,235

A holiday at Villa Natalie will not only delight your senses but it will also rejuvenate your love for all things Italian. This classically Tuscan ...more

Maremma Estate - Villa III

Cecina

Sleeps 8
Baths 4
Week starting at € 3,669

Maremma Estate is a stunning, 32 acre (13 hectares) estate located in ancient, Etruscan country, on the borderland of northern Maremma, and four ...more

Villa Maggie

Monteriggioni

Sleeps 8
Baths 4
Week starting at € 1,281

Villa Maggie sits in a splendidly secluded setting surrounded by green wooded hills and intriguing hamlets and castles. The old stone farmhouse has ...more

Sansepolcro

Sansepolcro Arezzo

Sleeps 7
Baths 2
Week starting at € 1,640

For a taste of history, experience "Sansepolcro," inhabited by the same noble family since 1600. The gated entrance leads you to the large and ...more

Villa Galante

Greve

Sleeps 7/8
Baths 3
Week starting at € 4,038

Villa Galante has 4 bedrooms an can accommodate 7 guests and with the use of a rollaway bed (at an extra charge) can sleep a total of 8 guests. ...more

Villa Pila

Poggisbonsi Tuscany

Sleeps 7
Baths 2
Week starting at € 1,219

Villa Pila is a beautiful independent villa located in the heart of the Chianti region between the two villages of Poggibonsi and Castellina. It is ...more

Villa Cora

Pieve

Sleeps 6
Baths 2
Week starting at € 808

Villa Cora, an independent farmhouse with private swimming pool, is one of six restored buildings situated within the property of a beautiful estate, ...more

Bellavista

Carmignano / Florence

Sleeps 6
Baths 2
Week starting at € 2,923

Bellavista is a lovely Florence villa rental located just west of Florence and above the village of Carmignano. It was built in the 1400's high in ...more

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Casa Fabrizio

Castiglione della Pescaia

Sleeps 6
Baths 2
Week starting at € 1,588

Casa Fabrizio is a spacious 3 bedroom home situated on the hills overlooking the Tyrolean Sea and several islands of the Tuscan Archipelago. It's a ...more

Villa Serene

Orbicciano/Lucca

Sleeps 6/8
Baths 4
Week starting at € 4,462

On November 13, 2001 Mr.G.C. of San Francisco comments "The property was just amazing!" The city of Lucca attracts tourists from around the world to ...more

Panorama 2

Siena / Asciano

Sleeps 6
Baths 2
Week starting at € 988

This country estate is composed of several buildings of historical and artistic importance; among them, the most beautiful is the main house with ...more

Valdarno - Casa Loggia

Pergine Valdarno

Sleeps 6/8
Baths 2
Week starting at € 1,038

Experience country living at Casa Loggia which is a recently restored Tuscan villa rental located in Pergine Valdarno. Not far from the main road, a ...more

Casa Loggia 1

Pergine Valdarno Ar

Sleeps 6
Baths 1
Week starting at € 863

This quaint home was once a barn and has been transformed into a little Tuscan hideaway surrounded by three hectares of fields, vineyards and ...more

La Castagnetta 4

San Gimignano / Il Castagno

Sleeps 6/8
Baths 3
Week starting at € 1,077

This estate is located on a hilltop and overlooks all the nearby valleys that extend as far as your eye can see. The History of this estate goes back ...more

Valdarno 4

Pergine Valdarno

Sleeps 6/8
Baths 2
Week starting at € 754

Valdarno is a group of newly renovated and well furnished apartments on a large estate in the center of Tuscany. The beautiful stone buildings date ...more

Casa Cappezano

Lucca / Cappezano Monte

Sleeps 6
Baths 4
Week starting at € 3,692

Casa Cappezano is situated high above Lucca near the village of Cappezano Monte. Here above olive orchards the owners have developed an outstanding ...more

La Cavallo

Siena / San Giovanni dAsso

Sleeps 6
Baths 2
Week starting at € 2,613

La Cavallo is a delightful 2 story house right inside the little hilltown of San Giovanni d’Asso, not far from Siena. Situated near a medieval ...more

Valdarno 5

Pergine Valdarno

Sleeps 6/8
Baths 2
Week starting at € 831

Valdarno is a group of newly renovated and well furnished apartments on a large estate in the center of Tuscany. The estate lies on the gentle hills ...more

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Casa Pieve

La Pieve San Stefano Lucca

Sleeps 6/8
Baths 2
Week starting at € 2,423

Casa Pieve is a delightful stone-built country house located just north of the charming town of Lucca. Positioned on a hillside, the home has ...more

Villa Montalcino

Montalcino

Sleeps 6/8
Baths 3
Week starting at € 4,062

Villa Montalcino is the perfect place to enjoy a relaxing holiday in a typical Tuscan countryside atmosphere together with the convenience of being ...more

Villa Signa

Signa

Sleeps 6/8
Baths 1
Week starting at € 1,346

Villa Signa is surrounded by a lush garden and is located in the ideal position to explore Tuscany. It is between the towns of Signa and Carmignano ...more

Villa Capannina

Forte dei Marmi

Sleeps 6/7
Baths 2
Week starting at € 1,958

Villa Capannina is an affordable, charming villa located in a quiet, residential neighborhood. Its lovely setting includes a nicely maintained ...more

Casa Brezza

Castigioncello

Sleeps 6/8
Baths 2
Week starting at € 715

The charming Casa Brezza is a hillside, ground floor apartment immersed in the pine woods of a residential area in the seaside village of ...more

Villa Annah

Camaiore

Sleeps 6/8
Baths 4
Week starting at € 3,173

Villa Annah is a nicely restored farm house consisting of the main house and an annex (formally the barn). It's situated on a hill near the charming, ...more

Villa Oliva Siena

Siena

Sleeps 6
Baths 3
Week starting at € 4,846

Villa Oliva Siena is an intimate country house immersed in the beautiful landscape just outside the town of Siena (3 km). Nestled amongst olive ...more

Casa Scuola

Lucca / Matraia

Sleeps 5
Baths 2
Week starting at € 1,354

Casa Scuola belongs to a charming little hamlet situated in the green hills of Matraia above the medieval town of Lucca. Originally built in the ...more

Panorama 1

Siena / Asciano

Sleeps 5
Baths 2
Week starting at € 952

This country estate is composed of several buildings of historical and artistic importance; among them, the most beautiful is the main house with its ...more

Apartment Luminoso

Siena

Sleeps 5
Baths 2
Week starting at € 1,115

Apartment Luminoso is a beautiful 1400 square foot, 3 bedroom 2 bath accommodation right in the center of the artistic and famous town of Siena. ...more

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La Castagnetta 2

San Gimignano / Il Castagno

Sleeps 5
Baths 2
Week starting at € 1,038

This estate is located on a hilltop and overlooks all the nearby valleys that extend as far as your eye can see. The History of this estate goes back ...more

Valdarno 3

Pergine Valdarno

Sleeps 5/7
Baths 2
Week starting at € 692

Valdarno is a group of newly renovated and well furnished apartments on a large estate in the center of Tuscany. The beautiful stone buildings date ...more

La Fortunata

Lucca / Aquilea

Sleeps 5/6
Baths 2
Week starting at € 1,648

La Fortunata is a well appointed house in a picturesque village just 5 miles outside Lucca. A classic old farmhouse that has been completely ...more

Vicario

Siena / Vico dArbia

Sleeps 4/6
Baths 2
Week starting at € 3,297

Vicario is in a small hamlet of villas just 8 km outside of Siena. Part of a country estate that still produces grains, olive oil, and wine, the ...more

Artista

Siena / Vico d\'Arbia

Sleeps 4
Baths 2
Week starting at € 2,522

L'Artista is sited in a small hamlet of homes just 8 km outside of Siena. This apartment is within a small gated community; the owner lives nearby. ...more

Fuoco

Siena / Isola D\\Arbia Siena

Sleeps 4/6
Baths 1
Week starting at € 692

Siena is just minutes away from this two hundred year old hamlet. Each building has been separated into several apartments and each has a remodeled ...more

Apartment Brava

Lucca, Tuscany

Sleeps 4
Baths 1
Week starting at € 1,454

Casa Bravissima is a recently, delightfully restored villa that instantly displays that old, rustic charm. This villa is located in the heart of ...more

Casa Scuola 1

Lucca / Matraia

Sleeps 4
Baths 1
Week starting at € 1,054

Casa Scuola 1 belongs to a charming little hamlet of two houses rentals situated in the green hills of Matraia above the medieval town of Lucca. ...more

Panorama 1

Siena / Asciano

Sleeps 4
Baths 2
Week starting at € 916

This country estate is composed of several buildings of historical and artistic importance; among them, the most beautiful is the main house with ...more

La Castagnetta 5

San Gimignano / Il Castagno

Sleeps 4
Baths 2
Week starting at € 846

This estate is located on a hilltop and overlooks all the nearby valleys that extend as far as your eye can see. The History of this estate goes back ...more

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La Toppina 2

Arezzo / Pieve al Toppo

Sleeps 4
Baths 1
Week starting at € 1,200

This hamlet dates back to the 18th Century and was occupied by villagers until 1940. The whole village has since been meticulously restored, and even ...more

Valdarno 2

Pergine Valdarno

Sleeps 4/6
Baths 1
Week starting at € 715

Valdarno is a group of newly renovated and well furnished apartments on a large estate in the center of Tuscany. The beautiful stone buildings date ...more

Castello Pietrasanta

lucca / Pietrasanta

Sleeps 4/6
Baths 2
Week starting at € 6,455

Castello Pietrasanta is a converted medieval castle (built in the 1200’s!) on the very crown of a hilltop village of Tuscany. Everything about it is ...more

Podere Fiore di Campo - Casa del Trifoglio

Asciano

Sleeps 4
Baths 2
Week starting at € 877

This glorious small group of buildings is situated in an enchanting panoramic location on top of one of the rolling hills of Tuscany. From every ...more

Podere Fiore di Campo - Casa del Stagno

Asciano

Sleeps 4
Baths 2
Week starting at € 877

This glorious small group of buildings is situated in an enchanting panoramic location on top of one of the rolling hills of Tuscany. From every ...more

Podere Fiore di Campo - Casa del Coriandolo

Asciano

Sleeps 4
Baths 2
Week starting at € 877

This glorious small group of buildings is situated in an enchanting panoramic location on top of one of the rolling hills of Tuscany. From every ...more

Podere Fiore di Campo - Casa del Primula

Asciano

Sleeps 4
Baths 2
Week starting at € 877

This glorious small group of buildings is situated in an enchanting panoramic location on top of one of the rolling hills of Tuscany. From every ...more

Podere Fiore di Campo - Casa del Anice

Asciano

Sleeps 4
Baths 2
Week starting at € 877

This glorious small group of buildings is situated in an enchanting panoramic location on top of one of the rolling hills of Tuscany. From every ...more

Villa Bellissima III

Buonconvento

Sleeps 4
Baths 2
Week starting at € 9,769

Villa Bellissima III is one of 5 villas on the estate and can accommodate four guests in it's spacious 2 bedroom suites. The foundation of Villa ...more

Villa Bellissima IV

Buonconvento

Sleeps 4
Baths 2
Week starting at € 6,538

Villa Bellissima IV is one of 5 villas on the estate and can accommodate four guests in it's spacious 2 bedroom suites. The foundation of Villa ...more

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Villa Katrina

Lucca

Sleeps 4/6
Baths 4
Week starting at € 7,842

Villa Katrina, located just 15 minutes from Lucca, is a unique and lovely villa that has recently been completely reconstructed on the foundation ...more

Apartment Camilla 2

Siena

Sleeps 4
Baths 2
Week starting at € 1,169

Apartments Camilla 1,2 and 3 are located on the 4th and top floor of an impressive historical building in the pedestrian center of the city of Siena. ...more

Villa Torre - Apartment 1

Siena

Sleeps 4
Baths 2
Week starting at € 700

Located in a wonderful position west of Siena, reached by a winding road through chestnut forests, stands the tiny hamlet of Villa Torre. On a grassy ...more

Apartment Camilla 3

Siena

Sleeps 4
Baths 1
Week starting at € 1,050

Apartments Camilla 1, 2 and 3 are located on the 4th and top floor of an impressive historical building in the pedestrian center of the city of ...more

Maremma Estate - Villa I

Cecina

Sleeps 4
Baths 2
Week starting at € 1,627

Maremma Estate is a stunning, 32 acre (13 hectares) estate located in ancient, Etruscan country, on the borderland of northern Maremma, and four ...more

Panorama 3

Siena / Asciano

Sleeps 3
Baths 2
Week starting at € 808

This country estate is composed of several buildings of historical and artistic importance; among them, the most beautiful is the main house with its ...more

La Castagnetta 6

San Gimignano / Il Castagno

Sleeps 3
Baths 2
Week starting at € 677

This estate is located on a hilltop and overlooks all the nearby valleys that extend as far as your eye can see. The History of this estate goes back ...more

Apartment Camilla 1

Siena

Sleeps 3
Baths 1
Week starting at € 981

Apartments Camilla 1, 2 and 3 are located on the 4th and top floor of an impressive historical building in the pedestrian center of the city of ...more

Villa Torre - Apartment 2

Siena

Sleeps 3
Baths 1
Week starting at € 631

Located in a wonderful position west of Siena, reached by a winding road through chestnut forests, stands the tiny hamlet of Villa Torre. On a grassy ...more

Fuoco 1

Siena / Isola D'Arbia Siena

Sleeps 2
Baths 1
Week starting at € 538

Siena is just minutes away from this two hundred year old hamlet. Each building has been separated into several apartments and each has a remodeled ...more

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Fuoco 2

Siena / Isola D'Arbia Siena

Sleeps 2/4
Baths 1
Week starting at € 577

Siena is just minutes away from this two hundred year old hamlet. Each building has been separated into several apartments rentals and each has a ...more

Apartment del Campo

Siena

Sleeps 2/3
Baths 1
Week starting at € 959

Apartment del Campo is located just steps from the heart and soul of the medieval town of Siena, the Piazza del Campo. The Piazza is host not only ...more

La Castagnetta 7

San Gimignano / Il Castagno

Sleeps 2
Baths 1
Week starting at € 505

This estate is located on a hilltop and overlooks all the nearby valleys that extend as far as your eye can see. The History of this estate goes back ...more

La Toppina 1

Arezzo / Pieve al Toppo

Sleeps 2
Baths 1
Week starting at € 734

This hamlet dates back to the 18th Century and was occupied by villagers until 1940. The whole village has since been meticulously restored, and even ...more

Valdarno 1

Pergine Valdarno

Sleeps 2/4
Baths 1
Week starting at € 615

Valdarno is a group of newly renovated and well furnished apartments on a large estate in the center of Tuscany. The beautiful stone buildings date ...more

Podere Fiore di Campo - Casa del Maggiorana

Asciano

Sleeps 2/4
Baths 1
Week starting at € 655

This glorious small group of buildings is situated in an enchanting panoramic location on top of one of the rolling hills of Tuscany. From every ...more

Podere Fiore di Campo - Casa del Geranio

Asciano

Sleeps 2/2
Baths 2
Week starting at € 788

This glorious small group of buildings is situated in an enchanting panoramic location on top of one of the rolling hills of Tuscany. From every ...more

Podere Fiore di Campo - Casa del Camomilla

Asciano

Sleeps 2
Baths 1
Week starting at € 655

This glorious small group of buildings is situated in an enchanting panoramic location on top of one of the rolling hills of Tuscany. From every ...more

Appartamenti Delfino

Follonica

Sleeps 2/2
Baths 1
Week starting at € 654

On the beautiful Gulf of Follonica, in the town of Follonica, are seven recently built apartments that are situated overlooking the sandy beach of ...more

Apartment Palio

Siena

Sleeps 2/3
Baths 1
Week starting at € 785

Apartment Palio is situated right off the pedestrian area of Siena city center. It's located on the ground floor of a two- story brick building and ...more

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Villa Torre - Apartment 3

Siena

Sleeps 2
Baths 1
Week starting at € 531

Located in a wonderful position west of Siena, reached by a winding road through chestnut forests, stands the tiny hamlet of Villa Torre. On a grassy ...more

 

Browse our Holiday Villas and houses in Tuscany!

Whether you are looking for a Tuscany Villa rental near Siena, luxury Tuscany villas in Lucca, or a house or villas to rent near Arezzo, San Gimignano or Montepulciano, scroll down our listing and find your Villa rental, house or Apartment in Tuscany now!

Villa rentals in Tuscany - Tuscany Villas for rent in Chianti, Lucca and Siena. Find Holiday villa rentals and houses for rent in Tuscany at Rentavilla.com


Tips for Traveling and Renting in Tuscany Villa Rentals

We invite you to glorious Tuscany — with hills draped in olive groves and Chianti vineyards, fortressed towns and medieval sky-scrapers, and artistic achievements on canvas, stone, and café plates. No wonder there’s a reverence in the way people discuss their visits to Tuscany, as if they’re carried away by the memory of a great love affair… Indeed, there’s just so much to love about this place! we’ll explore a few of our favorite Tuscan villages to whet your travel appetite. Let’s start with Florence’s little sister, Siena.

Siena:

Siena is a diminutive beauty holding its own in the shadow of majestic and powerful Florence, 35 miles to the north. With its picturesque setting and lovely medieval architecture and art, Siena is a treasure to be relished. It’s also a wonderful place to stroll around in and enjoy the sights, thanks to its many pedestrian-only streets. Before you amble into Siena’s lanes and flower-box accented courtyards, linger a bit in its heart, the Piazza il Campo, its main square. This impressive shell-shaped area is ringed by centuries old buildings in richly-colored red brick and stone with shops and cafes on the ground level. Here, you can nibble your riccirelli (almond macaroon cookie) or panforte (dense honey bread with fruit and nuts) and sip your cappuccino and people-watch after exploring the imposing City Hall, City Tower (Torre del Mangia), and Civic Museum (Museo Civico) that anchor the piazza. Come in the evening to get the true local flavor and avoid the crowds. Finally, near il Campo lies the fantastical Duomo (Siena’s cathedral), built in 1215 and expanded and renovated into the late 1300s. Outside, this architectural beauty is adorned with sculptures of Bible scenes, decorative columns, gargoyles, stained glass, and a bell tower. Its striking façade is reminiscent of Florence’s Duomo, with white, greenish black, and red marble striping its exterior. Inside, the treasures are many with 13th century frescoes, a mosaic floor, a gilded hexagonal dome, numerous statues, and works by artistic masters Donatello, Bernini, and Michelangelo. Aside from the everyday wonders of Siena, visitors can experience a beloved celebration of cultural pride and heritage with the Palio di Siena, a centuries old horse race and festival held each year on July 2nd and August 16th. This horse race is a fast and furious two-minute scramble by ten bare-back jockeys riding for glory. Loads and loads of dirt are dumped and smoothed over Siena’s main square to serve as the race track. This four-day event culminates in the race and the pre-race procession which has been described as a breathtaking affair of glitzy pageantry—think elaborately costumed drummers and trumpeters, armor-clad knights wielding swords, oxen pulling Palio relics poised in flower-draped carts, scores of colorful contrade flags, and hoards of cheering Sienans! The passion behind this cherished Siena tradition lies in the pride of each of its neighborhood affiliations or contrade. Siena is divided into 17 contrade, each with its own distinct colors and mascot, which you will see on flags, sculptures, and building walls. During the Palio, jockeys represent their contrada and are bedecked with its colors and symbols. Sienans are fundamentally attached to their contrada like family and considered to be of the contrada of their birth, no matter where they move. This experience truly offers an insider’s view of the Sienese culture. Now we’re off to another lovely hillside village, San Gimignano.

San Gimignano:

This medieval village, founded by the Etruscans, lies 900 feet high on a hill between Florence and Siena. It is best known for its medieval towers which once numbered in the 70s. During the Middle Ages, San Gimignano was situated on Via Francigena, the pilgrim’s road to Rome. Because of its location, it hosted many devout travelers and generated much wealth for the merchants who served them. Some of the merchants, who’d become rich selling the much-treasured saffron of this region, built lofty tower homes from which they could safely control the town and feud with their neighbors. Aside from competing for the title of tallest tower, these powerful merchants funded the many Romanesque frescoes, sculptures, and paintings that adorn San Gimignano’s churches and monasteries. Today, only 14 towers remain to dot the skyline but UNESCO has designated this village a World Heritage Site and it is worth seeing for its uniqueness. With nearby Chianti growing world-renowned red wine, San Gimignano brings its light and aromatic white wine to the table, Vernaccia di San Gimignano. Another agricultural specialty of this area is saffron, which as we’ve seen made many medieval merchants quite wealthy. It is said that saffron was deemed so valuable during the early 1200s, it was used as currency, in part, by San Gimignano’s Town Council to repay a debt. As you dine in San Gimignano’s eateries, look for the influence of saffron in the dishes. In the animal world, local cinghiale (wild boar) is featured in many of the Tuscan recipes here, from stews to salami. If you prefer to eat dessert first, you might opt for pinolata, a rich dish of custard and pine nuts. Finally, let’s look at the enchantment that awaits travelers to Lucca.

Lucca:

Only an hour from Florence by train lies lovely Lucca. What is particularly spectacular about this Tuscan village are its 12 foot high walls that encircle the old part of town in a four kilometer loop. Lucca’s ramparts date back 2,000 years beginning with a Roman wall, and have since been reinforced with additions during Medieval and Renaissance times. With the Florentines and Pisans safely kept at bay, the walls now serve as a park—thanks to the sensibility of Marie Louise, who received Lucca as a gift from brother Napoleon—and contribute to Lucca’s relaxed feeling. There are also many pedestrian-only streets that add to the slow pace and enjoyment of this village. Narrow streets wind through ancient buildings and open onto grand piazzas, Romanesque churches, the stunning San Martino Cathedral, and shops and cafes from which to rest and people-watch. A fun and interesting way to enjoy the beauty of Lucca is to bike along the top of its ramparts. The walls are wide and paved and it’s not uncommon to see chic Italian ladies in fashionable clothing cruising by on bicycles beside you. Rumor has it that the wall was also once used as a racetrack for sports car racing in years past. Circumnavigating Lucca by bike will take you about 20 to 30 minutes and burn some gelato or pasta calories. Speaking of pasta, proud Luccans distinguish themselves from other Tuscan villages with a dish that hints at its wealthy past. Historically, silk and banking made Luccan families exceedingly rich and funded their opulent tower homes that once framed Lucca’s skyline—now only the Guinigi Tower remains, which is topped with live oak trees. These wealthy families could afford the cost of extra eggs and thus the egg-laden traditional tortelli Lucchesi was born—golden rich ravioli stuffed with meat and sauced with meat ragu. After one bite, it makes one think that Lucca’s ramparts may have actually been built to keep the Florentines away from their pasta! Luccan composer, Puccini, may written his best work after consuming some tortelli Lucchesi. You may wish to have a dish as well before attending a concert in the festival to honor Puccini during the July and August months.


 

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