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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 101 villas
Save $1,010 Photo of Beautiful Farmhouse in the Chianti Near Town
  • min $5,775/wk
  • max $10,098/wk
  • min $5,198/wk
  • max $9,088/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,010 when you book by Jun-20-2019**
" We had a wonderful, peaceful time...." - Davis
Save $242 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,441/wk
  • max $2,417/wk
  • min $1,297/wk
  • max $2,175/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $242 when you book by Jun-20-2019**
" Wonderful! The service was wonderful, the owners so gracious and friendly. ..." - Kathryn
Save $147 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $976/wk
  • max $1,472/wk
  • min $878/wk
  • max $1,325/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $147 when you book by Jun-20-2019**
" It was amazing. Everything was very well done...." - Simin
Save $956 Photo of Chianti Villa near a Charming Village
  • min $5,146/wk
  • max $9,557/wk
  • min $4,631/wk
  • max $8,601/wk
  • Min Stay: 3 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $956 when you book by Jun-20-2019**
" Everything was fine...." - William
Save $269 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,672/wk
  • max $2,689/wk
  • min $1,505/wk
  • max $2,420/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $269 when you book by Jun-20-2019**
" Tuscany at its best, staff treated us like family and the villa was outstanding...." - Buster
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 Jun-20-2019**
" Very happy; would go again...." - Karen
Save $256 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,513/wk
  • max $2,561/wk
  • min $1,362/wk
  • max $2,305/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $256 when you book by Jun-20-2019**
" This property is excellent. The owners are the most wonderful people. They were always gracious, helpful and friendly. We had a two bedroom apartment with a rea..." - Julie
Save $150 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,000/wk
  • max $1,504/wk
  • min $900/wk
  • max $1,354/wk
  • Min Stay: 5 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $150 when you book by Jun-20-2019**
" Overall, the experience was positive. The apartment and grounds were spotless, exactly the way I like my home in the U.S. The family is very nice, attentive and he..." - Michelle
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 Jun-20-2019**
" A wonderful experience. We'd definitely go again but would probably choose an apartment at the villa with more windows. ..." - Margaret
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 Jun-20-2019**
" Perfect!!! Beyond our expectations!!!..." - Rebecca
Save $338 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,969/wk
  • max $3,376/wk
  • min $1,772/wk
  • max $3,038/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $338 when you book by Jun-20-2019**
" It's an amazing property. We had space galore and help when we needed it. The location is very central in Tuscany, so it makes a great home base for daily excu..." - Steven
  • min $2,057/wk
  • max $3,665/wk
  • Min Stay: 5 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
" 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 $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 Jun-20-2019**
" 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 $291 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,689/wk
  • max $2,913/wk
  • min $1,520/wk
  • max $2,622/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 $291 when you book by Jun-20-2019**
" Amazing! We felt like we were part of a family on the property - Sandra, Nicolo, and all the staff were so friendly and helpful. The whole experience made us fee..." - Rayna
Save $318 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,784/wk
  • max $3,184/wk
  • min $1,606/wk
  • max $2,866/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $318 when you book by Jun-20-2019**
" We four girls absolutely LOVED it! It was what I imagined. The owners are VERY dedicated!..." - Lynn
Save $200 Photo of Pleasant Tuscan Apartment on Large Hillside Estate
  • min $1,248/wk
  • max $2,001/wk
  • min $1,123/wk
  • max $1,801/wk
  • Min Stay: 5 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $200 when you book by Jun-20-2019**
" Wonderful!..." - Peter
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 Jun-20-2019**
" 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 Jun-20-2019**
" Enjoyed my stay at the villa. Management ia very friendly and helpful...." - Sharon
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 Jun-20-2019**
" The room had a feeling of gracious elegance, dark wood furnishings, wardrobe, end tables and bureau. It was very spacious, comfortable, and convenient...." - Neil
  • $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 Jun-20-2019**
" The location was perfect, both in relation to the town, and to the parking...." - Christine
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 Jun-20-2019**
" 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 $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 Jun-20-2019**
" Very good. We were upgraded us to a larger unit...." - Donna
Save $250 Photo of Apartment within a Villa in Southern Tuscany
  • min $2,059/wk
  • max $2,500/wk
  • min $1,853/wk
  • max $2,250/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $250 when you book by Jun-20-2019**
" Amazing! Staying here was like being in paradise. ..." - Cassandra
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 Jun-20-2019**
" The size of the bedrooms, bathrooms and the outside patio area...." - Monica
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 Jun-20-2019**
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 Jun-20-2019**
Save $713 Photo of Farmhouse Rental in Chianti Area of Tuscany
  • min $3,277/wk
  • max $7,127/wk
  • min $2,949/wk
  • max $6,414/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $713 when you book by Jun-20-2019**
" We thoroughly enjoyed ourselves and were happy with the villa. The location was awesome. We traveled throughout Tuscany and found the villa to be centrally locat..." - Maurice
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 Jun-20-2019**
Save $216 Photo of Family-Friendly Apartment Close to Siena
  • min $1,133/wk
  • max $2,162/wk
  • min $1,020/wk
  • max $1,946/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $216 when you book by Jun-20-2019**
" Overall the property and atmosphere were great. The location was convenient to Siena and we found this to be very enjoyable, much more so than Florence...." - Peter
Save $137 Photo of Holiday Apartment in the Center of San Gimignano
  • $1,371/wk
  • $1,234/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Washing Machine
** Save up to $137 when you book by Jun-20-2019**
" This property is well situated and is quite comfortable for 2 couples...." - Sonia
 
Displaying 61 to 90 of 101 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..