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Siena Villas and Vacation Rentals

Nestled amidst the hills and valleys of the Sienese Chianti-a territory dominated by medieval hill towns---Siena offers a wonderfully preserved example of the Tuscan Middle Ages. The city is home to many Gothic palaces, churches, and museums filled with Gothic art.   Continue >

Displaying 61 to 90 of 99 villas
Save $144 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $944/wk
  • max $1,441/wk
  • min $850/wk
  • max $1,297/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $144 when you book by Aug-31-2019**
" Perfect!!! Beyond our expectations!!!..." - Rebecca
Save $216 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,280/wk
  • max $2,161/wk
  • min $1,152/wk
  • max $1,945/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $216 when you book by Aug-31-2019**
" Very happy; would go again...." - Karen
Save $925 Photo of Farmhouse Rental in Tuscany, Gaiole in Chianti (Chianti Area)
  • min $8,110/wk
  • max $9,245/wk
  • min $7,299/wk
  • max $8,321/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $925 when you book by Aug-31-2019**
" We took this trip to celebrate our 40th anniversary. We were joined by our three adult children and their significant others and our grandson. We had a wonderful..." - Mark
Save $952 Photo of Tuscan farmhouse with pool a rural retreat in the Crete Senesi near Siena
  • min $3,815/wk
  • max $9,520/wk
  • min $3,434/wk
  • max $8,568/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $952 when you book by Aug-31-2019**
Save $367 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $2,057/wk
  • max $3,665/wk
  • min $1,851/wk
  • max $3,299/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $367 when you book by Aug-31-2019**
" Except for a cooking class at the estate, we spent our time traveling to Siena, Florence, Cinque Terre, and the Chianti region during our 5 night stay. I'd ra..." - Bob
Save $192 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,168/wk
  • max $1,920/wk
  • min $1,051/wk
  • max $1,728/wk
  • Min Stay: 5 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $192 when you book by Aug-31-2019**
" A wonderful experience. We'd definitely go again but would probably choose an apartment at the villa with more windows. ..." - Margaret
Save $169 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,105/wk
  • max $1,689/wk
  • min $995/wk
  • max $1,520/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $169 when you book by Aug-31-2019**
" This was a wonderful experience. Ricardo, Sandra and Simona were always helpful and responsive. They helped us work on our Italian language skills with a smile a..." - Ellen
Save $335 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,945/wk
  • max $3,346/wk
  • min $1,751/wk
  • max $3,011/wk
  • Min Stay: 5 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $335 when you book by Aug-31-2019**
" Enjoyed my stay at the villa. Management ia very friendly and helpful...." - Sharon
Save $340 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
  • min $2,615/wk
  • max $3,399/wk
  • min $2,354/wk
  • max $3,059/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
** Save up to $340 when you book by Aug-31-2019**
" Very good...." - Kenneth
Save $412 Photo of Apartment Rental in the Center of Siena
  • min $2,842/wk
  • max $4,116/wk
  • min $2,558/wk
  • max $3,704/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $412 when you book by Aug-31-2019**
" Very good. The property was well located. ..." - Rick
  • min $19,603/wk
  • max $22,403/wk
  • Min Stay: 7 days
Sleeps 25 people
  • 3 single bedrooms
  • 11 double bedrooms
  • 14 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
" The villa was lovely...." - Phyllis
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 Aug-31-2019**
" Absolutely wonderful. Experience enhanced by the warm hospitality of Claudia and Rudy - we left feeling like family friends not hospitality guests...." - Kay
  • $915/wk
  • $824/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $92 when you book by Aug-31-2019**
" The location was perfect, both in relation to the town, and to the parking...." - Christine
Save $341 Photo of Apartment for a Family in the Center of Siena
  • min $2,352/wk
  • max $3,411/wk
  • min $2,117/wk
  • max $3,070/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $341 when you book by Aug-31-2019**
" We had a great time. The property was in excellent condition. Anthony received us well and explained everything we needed and answered all of our questions. ..." - Andy
Save $2,743 Photo of Historic Tuscan Villa with Cottage with Private Pool and Tennis Court
  • min $18,357/wk
  • max $27,430/wk
  • min $16,521/wk
  • max $24,687/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,743 when you book by Aug-31-2019**
Save $370 Photo of Villa Rental in Tuscany, Castellina in Chianti (Chianti Area)
  • min $1,031/wk
  • max $3,697/wk
  • min $928/wk
  • max $3,327/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 $370 when you book by Aug-31-2019**
Save $1,488 Photo of Large Chianti Classico Villa with Swimming Pool and Spa near Siena
  • min $11,611/wk
  • max $14,877/wk
  • min $10,450/wk
  • max $13,389/wk
  • Min Stay: 3 days
Sleeps 18 people
  • 9 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,488 when you book by Aug-31-2019**
Save $265 Photo of Family-Friendly Apartment Close to Siena
  • min $1,452/wk
  • max $2,645/wk
  • min $1,307/wk
  • max $2,381/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $265 when you book by Aug-31-2019**
" Very good. We were upgraded us to a larger unit...." - Donna
Save $1,103 Photo of Villa in Southern Tuscany with Privacy and Views
  • min $8,400/wk
  • max $11,025/wk
  • min $7,560/wk
  • max $9,923/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,103 when you book by Aug-31-2019**
" Very good...." - Bill
Save $467 Photo of Villa near Montalcino
  • min $3,360/wk
  • max $4,667/wk
  • min $3,024/wk
  • max $4,200/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $467 when you book by Aug-31-2019**
" It was like our own villa. The owners were so helpful in making everything work and we enjoyed our holiday. The sun room was a special place. We set it up as o..." - Geoff
Save $112 Photo of Holiday Apartment in the Center of San Gimignano
  • min $915/wk
  • max $1,121/wk
  • min $824/wk
  • max $1,009/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $112 when you book by Aug-31-2019**
" The room had a feeling of gracious elegance, dark wood furnishings, wardrobe, end tables and bureau. It was very spacious, comfortable, and convenient...." - Neil
Save $2,120 Photo of Villa Rental in Tuscany, Castellina in Chianti (Chianti Area)
  • $21,198/wk
  • $19,078/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,120 when you book by Aug-31-2019**
Save $782 Photo of Charming Farmhouse on a Large Estate in Monticchiello
  • min $5,822/wk
  • max $7,822/wk
  • min $5,240/wk
  • max $7,040/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $782 when you book by Aug-31-2019**
Save $312 Photo of Charming Apartment on a Large Estate in Monticchiello
  • min $2,353/wk
  • max $3,117/wk
  • min $2,118/wk
  • max $2,805/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $312 when you book by Aug-31-2019**
Save $309 Photo of Family-Friendly Apartment Close to Siena
  • min $1,616/wk
  • max $3,088/wk
  • min $1,454/wk
  • max $2,779/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $309 when you book by Aug-31-2019**
" The size of the bedrooms, bathrooms and the outside patio area...." - Monica
Save $1,615 Photo of Villa Rental in Tuscany, San Casciano dei Bagni
  • min $13,818/wk
  • max $16,149/wk
  • min $12,436/wk
  • max $14,534/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $1,615 when you book by Aug-31-2019**
Save $535 Photo of Villa Rental in Tuscany, Sarteano
  • min $1,042/wk
  • max $5,353/wk
  • min $938/wk
  • max $4,818/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $535 when you book by Aug-31-2019**
Save $535 Photo of Farmhouse Rental in Tuscany, Sarteano
  • min $1,042/wk
  • max $5,353/wk
  • min $938/wk
  • max $4,818/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $535 when you book by Aug-31-2019**
Save $1,470 Photo of Farmhouse Rental in Tuscany, Pienza
  • min $9,800/wk
  • max $14,700/wk
  • min $8,820/wk
  • max $13,230/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 2 single bedrooms
  • 6 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,470 when you book by Aug-31-2019**
Save $902 Photo of Tuscan Farmhouse with Private Pool and Beautiful Views
  • min $5,880/wk
  • max $9,016/wk
  • min $5,292/wk
  • max $8,114/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $902 when you book by Aug-31-2019**
 
Displaying 61 to 90 of 99 villas

Dating back to 1310, the Palio delle Contrade is an annual bareback horse race in which 10 of the city's 17 contrade (neighborhoods) compete. The culminating event of Italy's most spectacular festival, the biggest race is held on August 16; a smaller race is held on July 2nd. In the environs of Radda in Chianti, wine estates such as Castello di Volpaia and Badia a Coltibuono are satisfying side trips for wine and olive oil lovers. Heading northwest of Siena towards San Gimignano, Monteriggioni, one of Italy's most perfectly preserved fortified villages, dominates the vista..