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Tuscany Holidays

A hilly region rich in agriculture, Tuscany was the home of the Etruscan civilization, and later the birthplace of the Renaissance. It's known for charming, historic towns like Siena, Arezzo, Cortona, Lucca, San Gimignano, and Volterra.   Continue >

Displaying 61 to 90 of 437 villas
Save $118 Photo of Tuscany Holiday Apartment
  • min $932/wk
  • max $1,177/wk
  • min $839/wk
  • max $1,059/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $118 when you book by Jan-31-2020**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
Save $1,689 Photo of Large Historic Luxury Villa Near Lucca
  • min $13,390/wk
  • max $16,890/wk
  • min $12,051/wk
  • max $15,201/wk
  • Min Stay: 7 days
Sleeps 22 people
  • 11 double bedrooms
  • 15 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,689 when you book by Jan-31-2020**
" Perfect. ..." - Joy
Save $518 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $2,451/wk
  • max $5,181/wk
  • min $2,206/wk
  • max $4,663/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $518 when you book by Jan-31-2020**
" Absolutely excellent. ..." - Kerby
Save $4,947 Photo of Castle Rental in Tuscany, Montespertoli (Chianti Area)
  • min $26,078/wk
  • max $49,471/wk
  • min $23,470/wk
  • max $44,524/wk
  • Min Stay: 7 days
Sleeps 80 to 120 people
  • 1 single bedrooms
  • 42 double bedrooms
  • 35 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $4,947 when you book by Jan-31-2020**
Save $3,851 Photo of Private luxury villa near Florence with pool, tennis court, beautiful gardens, spectacular views.
  • min $17,503/wk
  • max $38,505/wk
  • min $15,753/wk
  • max $34,655/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,851 when you book by Jan-31-2020**
Save $196 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,470/wk
  • max $1,960/wk
  • min $1,323/wk
  • max $1,764/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $196 when you book by Jan-31-2020**
Save $824 Photo of Tuscan Farmhouse with Views and Private Pool
  • min $3,903/wk
  • max $8,243/wk
  • min $3,513/wk
  • max $7,419/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $824 when you book by Jan-31-2020**
" We had an amazing time with family friends! There was ample room inside out for smaller gatherings of children, teens and adults...." - Patricia
Save $289 Photo of Farmhouse near Village on Wine Estate
  • min $2,415/wk
  • max $2,888/wk
  • min $2,174/wk
  • max $2,599/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $289 when you book by Jan-31-2020**
" Wonderfull combination of privacy and proximity. Working vineyard was a real plus!..." - Michael
Save $1,362 Photo of Private Country Estate in Tuscany
  • min $5,558/wk
  • max $13,622/wk
  • min $5,002/wk
  • max $12,260/wk
  • Min Stay: 4 days
Sleeps 20 people
  • 10 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,362 when you book by Jan-31-2020**
" Absolutely beautiful with a nice Tuscan feel. The pool and outdoor loggia were very lovely. We spent a lot of time outside with wine and watching a beautiful sunse..." - Sujata
Save $157 Photo of Family-Friendly Apartment Close to Siena
  • min $1,030/wk
  • max $1,565/wk
  • min $927/wk
  • max $1,409/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Jan-31-2020**
" The time spent at Terra di Siena was wonderful and I would go back in a heartbeat...." - Vallerie
Save $118 Photo of Apartment Farmhouse in Tuscany
  • min $932/wk
  • max $1,177/wk
  • min $839/wk
  • max $1,059/wk
  • Min Stay: 4 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $118 when you book by Jan-31-2020**
" it exceeded our expectation. Claudia and Rudy were the perfect host, made use feel like family right from the start. invited us to partake in making and cooking re..." - Katheryn
Save $882 Photo of Villa Rental in Tuscany, Prato
  • min $4,900/wk
  • max $8,820/wk
  • min $4,410/wk
  • max $7,938/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $882 when you book by Jan-31-2020**
Save $588 Photo of Villa Rental in Tuscany, Camaiore
  • min $4,314/wk
  • max $5,876/wk
  • min $3,883/wk
  • max $5,288/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $588 when you book by Jan-31-2020**
Save $962 Photo of Rustic Tuscan Villa Surrounded by Olive Groves and Vineyards
  • $9,615/wk
  • $8,654/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $962 when you book by Jan-31-2020**
" It was very pleasant. Getting there late at night and having a bottle of wine and homemade lasagna, olive oil and bread, was a very welcomed surprise...." - Janice
Save $342 Photo of Accommodation Cortona Tuscany
  • min $730/wk
  • max $3,416/wk
  • min $657/wk
  • max $3,074/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $342 when you book by Jan-31-2020**
" Liked it...." - John
Save $2,940 Photo of Villa Rental in Tuscany, Lucca
  • min $25,200/wk
  • max $29,400/wk
  • min $22,680/wk
  • max $26,460/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,940 when you book by Jan-31-2020**
Save $123 Photo of Farmhouse Accommodation in Tuscany
  • min $961/wk
  • max $1,230/wk
  • min $865/wk
  • max $1,107/wk
  • Min Stay: 4 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $123 when you book by Jan-31-2020**
" Beautiful stay...." - Joan
Save $980 Photo of Villa Rental in Tuscany, Gambassi Terme
  • min $6,791/wk
  • max $9,802/wk
  • min $6,112/wk
  • max $8,822/wk
  • Min Stay: 3 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $980 when you book by Jan-31-2020**
" Overall we had a good week. ..." - Phil
Save $211 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,617/wk
  • max $2,107/wk
  • min $1,455/wk
  • max $1,896/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $211 when you book by Jan-31-2020**
Save $142 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,078/wk
  • max $1,421/wk
  • min $970/wk
  • max $1,279/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $142 when you book by Jan-31-2020**
" It was the most wonderful place. So very near Firenze and yet in the quiet and lovely countryside. The administrator was very helpful and charming. We enjoy every ..." - Susana
Save $142 Photo of Ancient Hamlet in Tuscany near Florence
  • min $1,078/wk
  • max $1,421/wk
  • min $970/wk
  • max $1,279/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $142 when you book by Jan-31-2020**
Save $283 Photo of Tuscany Farmhouse with a Private Pool
  • min $1,681/wk
  • max $2,833/wk
  • min $1,513/wk
  • max $2,550/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $283 when you book by Jan-31-2020**
" The location of the property was superb. Overall experience was a positive one. The owners, Rita and Roberto, were helpful and delightful...." - Trudy
Save $154 Photo of Holiday Accommodation in Chianti
  • min $771/wk
  • max $1,541/wk
  • min $694/wk
  • max $1,387/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Jan-31-2020**
" Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
Save $576 Photo of Tuscany Villa with Pool Near the Beach
  • min $3,640/wk
  • max $5,758/wk
  • min $3,276/wk
  • max $5,182/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $576 when you book by Jan-31-2020**
" The six of us agreed that the villa was exactly as advertised and we had a great week enjoying it...." - John
Save $251 Photo of Charming Villa in Tuscany On the Edge of an Authentic Hill Town
  • min $1,440/wk
  • max $2,511/wk
  • min $1,296/wk
  • max $2,260/wk
  • Min Stay: 5 days
Sleeps 2 to 4 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $251 when you book by Jan-31-2020**
" Amazing! It was so beautiful and private and serene. Perfect place to be in Tuscany...." - Ben
Save $1,442 Photo of Large Luxury Villa Close To Lucca with Pool and Chapel
  • min $10,255/wk
  • max $14,420/wk
  • min $9,230/wk
  • max $12,978/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $1,442 when you book by Jan-31-2020**
" We were amazed with the absolute beauty of the villa, grounds and interior. It was PERFECT for us. And Angelo the owner was so nice and kind we enjoyed talking to ..." - Robert
Save $588 Photo of Charming Villa with Pool in Tuscany
  • min $2,801/wk
  • max $5,881/wk
  • min $2,521/wk
  • max $5,293/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $588 when you book by Jan-31-2020**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $257 Photo of Family-Friendly Farmhouse Close to Siena
  • min $1,338/wk
  • max $2,573/wk
  • min $1,204/wk
  • max $2,316/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $257 when you book by Jan-31-2020**
" The view of the hills, grape orchard, and olive trees...." - Ann
Save $1,909 Photo of Large Chic Tuscany Villa with Private Guest House and Al Fresco Dining
  • min $12,163/wk
  • max $19,093/wk
  • min $10,947/wk
  • max $17,184/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,909 when you book by Jan-31-2020**
" Our 4 weeks at Villa Brunello were everything we could have dreamed and more! The PERFECT Tuscan experience in every way!..." - Matt
Save $707 Photo of Versilia Villa with Pool near Town
  • min $2,870/wk
  • max $7,070/wk
  • min $2,583/wk
  • max $6,363/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $707 when you book by Jan-31-2020**
" The pool and the views...." - Karen
 
Displaying 61 to 90 of 437 villas

A destination for gourmands, the wine of Tuscany's Chianti region is famous around the globe. Extra virgin Tuscan olive oil, a staple in regional cuisine, is also highly prized. Tuscany's capital, Florence is a great art center whose centro storico remains closely linked to its medieval past, in spite of tourist crowds. The region's Tyrrhenian coast is famous for its white sand beaches and pine forests. Come August, Florentines depart en masse for spots such as Viareggio, Forte dei Marmi, and the island of Elba. A Tuscany villa rental is the ideal way to experience the region as it provides a comfortable base from which to explore while also providing the perfect place to rejoice and share after a day of adventures..