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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 443 villas
Save $133 Photo of Tuscan Apartment in Historic Castle
  • min $679/wk
  • max $1,328/wk
  • min $611/wk
  • max $1,195/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $133 when you book by Jul-20-2020**
" The castle is beautiful...." - Serena
Save $125 Photo of Tuscan Apartment in Historic Castle
  • min $763/wk
  • max $1,252/wk
  • min $687/wk
  • max $1,127/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $125 when you book by Jul-20-2020**
" Ambiance. Staff was very good...." - Will
Save $183 Photo of Tuscan Apartment in Historic Castle
  • min $927/wk
  • max $1,825/wk
  • min $834/wk
  • max $1,643/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $183 when you book by Jul-20-2020**
" We absolutely loved our time at Il Castello 27! Our family loved the property and the people that worked there were so friendly and helpful!..." - Sharon
Save $170 Photo of Tuscan Apartment in Historic Castle
  • min $772/wk
  • max $1,699/wk
  • min $695/wk
  • max $1,529/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $170 when you book by Jul-20-2020**
" The location was very good. Easy driving to some of the towns we wanted to visit, such as Pisa, Lucca and Siena. The beds were comfortable and the villa was roomy..." - Cheryl
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 Jul-20-2020**
" Beautiful stay...." - Joan
Save $308 Photo of Apartment Rental in Florence City, Duomo
  • min $2,834/wk
  • max $3,084/wk
  • min $2,551/wk
  • max $2,776/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Washing Machine
  • Air Conditioning
** Save up to $308 when you book by Jul-20-2020**
Save $2,042 Photo of Villa Rental in Tuscany, Strada in Chianti
  • min $11,669/wk
  • max $20,419/wk
  • min $10,502/wk
  • max $18,377/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $2,042 when you book by Jul-20-2020**
Save $1,050 Photo of Villa Rental in Tuscany, Vorno
  • min $7,001/wk
  • max $10,502/wk
  • min $6,301/wk
  • max $9,452/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,050 when you book by Jul-20-2020**
Save $145 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $944/wk
  • max $1,449/wk
  • min $850/wk
  • max $1,304/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $145 when you book by Jul-20-2020**
Save $528 Photo of Villa Rental in Tuscany, Viareggio
  • min $2,898/wk
  • max $5,278/wk
  • min $2,608/wk
  • max $4,750/wk
  • Min Stay: 7 days
Sleeps 6 to 8 people
  • 3 double bedrooms
  • 4 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $528 when you book by Jul-20-2020**
Save $2,310 Photo of Villa Rental in Tuscany, Castelfalfi
  • min $14,630/wk
  • max $23,100/wk
  • min $13,167/wk
  • max $20,790/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,310 when you book by Jul-20-2020**
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 Jul-20-2020**
" The location of the property was superb. Overall experience was a positive one. The owners, Rita and Roberto, were helpful and delightful...." - Trudy
Save $1,378 Photo of Beautiful Tuscan Villa with Tower and Private Swimming Pool near Florence
  • min $8,860/wk
  • max $13,782/wk
  • min $7,974/wk
  • max $12,404/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,378 when you book by Jul-20-2020**
" Beautiful villa...." - Mary Beth
Save $1,141 Photo of Beautiful Tuscan Villa Near Lucca with Views and Private Pool
  • min $7,193/wk
  • max $11,410/wk
  • min $6,474/wk
  • max $10,269/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,141 when you book by Jul-20-2020**
" It was fantastic! The attention to detail in the architecture and furnishing was beautiful. ..." - Samantha
Save $1,358 Photo of Private Villa on a Castle Estate near Certaldo
  • min $9,102/wk
  • max $13,582/wk
  • min $8,192/wk
  • max $12,224/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,358 when you book by Jul-20-2020**
" The villa was in the most beautiful setting, the staff was absolutely fantastic and we enjoyed getting to know them and they took such good care of our large group..." - Vesna
Save $261 Photo of Tuscan Apartment in Historic Castle
  • min $1,454/wk
  • max $2,611/wk
  • min $1,309/wk
  • max $2,350/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $261 when you book by Jul-20-2020**
" Overall our stay at the villa was a wonderful experience and the views amazing. Just wish we could have stayed around long enough to enjoy more!..." - Anne
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 Jul-20-2020**
" Overall we had a good week. ..." - Phil
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 Jul-20-2020**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
Save $273 Photo of Villa Rental Very Close to Cortona
  • min $1,680/wk
  • max $2,730/wk
  • min $1,512/wk
  • max $2,457/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $273 when you book by Jul-20-2020**
" We all had an absolutely fabulous time. The villa was delightful , even better than I had hoped . It was extremely comfortable , full of atmosphere and in a gre..." - Julianne
Save $1,294 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
  • min $7,106/wk
  • max $12,938/wk
  • min $6,395/wk
  • max $11,644/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,294 when you book by Jul-20-2020**
" Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
Save $680 Photo of Private Italian Luxury Villa Near Historic Cortona
  • min $4,586/wk
  • max $6,804/wk
  • min $4,127/wk
  • max $6,124/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $680 when you book by Jul-20-2020**
" Great...." - Ed
Save $529 Photo of Tuscany Farmhouse with Pool for Families
  • min $3,623/wk
  • max $5,285/wk
  • min $3,261/wk
  • max $4,757/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Air Conditioning
** Save up to $529 when you book by Jul-20-2020**
" Excellent property! Comfortable and cozy with lots of room for four people. Nicely landscaped yard large enough to walk around...." - Kevin
Save $576 Photo of Tuscan Farmhouse with Views and Private Pool
  • min $2,818/wk
  • max $5,758/wk
  • min $2,536/wk
  • max $5,182/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $576 when you book by Jul-20-2020**
" We had a fabulous time. We were hoping for a quiet, well appointed Tuscany villa overlooking a valley with olive trees and got precisely that...." - Peter
Save $971 Photo of Large Villa Rental in Tuscany Near Florence with Pool
  • min $6,721/wk
  • max $9,708/wk
  • min $6,049/wk
  • max $8,737/wk
  • Min Stay: 5 days
Sleeps 20 people
  • 2 single bedrooms
  • 9 double bedrooms
  • 11 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $971 when you book by Jul-20-2020**
" A wonderful two weeks was thoroughly enjoyed by our entire family of 20 people aged from 4 years up to 70 years. Facilities were excellent in every respect and ass..." - Terry
Save $404 Photo of Farmhouse Rental in Tuscany, Montalcino
  • min $2,399/wk
  • max $4,039/wk
  • min $2,159/wk
  • max $3,635/wk
  • Min Stay: 7 days
Sleeps 7 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $404 when you book by Jul-20-2020**
" Very cozy property, although a tiny kitchen for a property of that size...." - Anne
Save $602 Photo of Exclusive  Hilltop  Medieval  Villa  Features  Modern  Comforts,  Panoramic  Sea  Views,  Garden,  Pool  and  Jacuzzi  in  Pistoia,  Tuscany
  • min $2,661/wk
  • max $6,021/wk
  • min $2,395/wk
  • max $5,419/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $602 when you book by Jul-20-2020**
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 Jul-20-2020**
" 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 Jul-20-2020**
" Wonderfull combination of privacy and proximity. Working vineyard was a real plus!..." - Michael
Save $546 Photo of Self-Catering Accommodation for Family near Lucca
  • min $2,590/wk
  • max $5,460/wk
  • min $2,331/wk
  • max $4,914/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $546 when you book by Jul-20-2020**
" We loved the property. The view was breathtaking. It was convenient to many sites like Florence, Cinque Terre, Pisa etc. It was our first "villa experience&qu..." - William
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 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Jul-20-2020**
" The people managing the property are first class. Very conscientious and helpful. ..." - Bo
 
Displaying 61 to 90 of 443 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..