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Vacation Accommodation Chianti Tuscany Villa Rentals

South of Florence lies the Chianti, Italy's definitive wine-growing region. This area boasts hills covered in vineyards, winding roads (favored by sporty drivers and daredevil cyclists), and breathtaking vistas.   Continue >

Displaying 1 to 30 of 179 villas
Save $434 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,190/wk
  • max $4,337/wk
  • min $1,971/wk
  • max $3,903/wk
  • Min Stay: 3 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $434 when you book by Feb-20-2019**
" Couldn't have been any better. Loved every minute...." - Kathy
Save $784 Photo of Beautiful Large Villa Close to Florence
  • min $5,601/wk
  • max $7,841/wk
  • min $5,041/wk
  • max $7,057/wk
  • Min Stay: 5 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $784 when you book by Feb-20-2019**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $356 Photo of Tuscany Villa Rental in Chianti
  • min $2,077/wk
  • max $3,558/wk
  • min $1,869/wk
  • max $3,202/wk
  • Min Stay: 5 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $356 when you book by Feb-20-2019**
" The experience was amazing. It was two perfect weeks...." - Michael
Save $297 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • min $2,075/wk
  • max $2,967/wk
  • min $1,868/wk
  • max $2,670/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $297 when you book by Feb-20-2019**
" The overall experience can be best described in one word- magnifica! We would highly recommend this villa because it had everything we could possible need. It is d..." - Paula
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 Feb-20-2019**
" Overall we had a good week. ..." - Phil
Save $1,284 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,780/wk
  • max $3,235/wk
  • min $1,073/wk
  • max $2,209/wk
  • Min Stay: 5 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,284 when you book by Feb-20-2019**
" Fantastic, better than our high expectations!..." - Harri
  • min $673/wk
  • max $971/wk
  • min $606/wk
  • max $874/wk
  • Min Stay: 7 days
Sleeps 3 to 4 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $97 when you book by Feb-20-2019**
" We had a amazing time in Tuscany and loved our little villa!..." - Melissa
Save $336 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,226/wk
  • max $1,667/wk
  • min $993/wk
  • max $1,500/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $336 when you book by Feb-20-2019**
" It was a beautiful property and the staff was exceptional especially helping us through a difficult situation we encountered. We would return!..." - Kim
Save $163 Photo of One of Four Apartments on Large Tuscan Estate
  • min $1,401/wk
  • max $1,625/wk
  • min $1,261/wk
  • max $1,463/wk
  • Min Stay: 7 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $163 when you book by Feb-20-2019**
" One of our favourite areas on our month-long trip in Italy. After staying in Florence this was such a pleasant, quiet week with gorgeous scenery, pool and friendl..." - Susan
Save $391 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,059/wk
  • min $1,192/wk
  • max $1,668/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $391 when you book by Feb-20-2019**
" This was the most wonderful experience I have ever had. Think of the movie Under the Tuscan Sun... well, this villa is exactly that on steroids! So romantic, staf..." - Jackie
Save $155 Photo of Charming Apartment in Chianti Overlooking the Countryside
  • min $953/wk
  • max $1,550/wk
  • min $858/wk
  • max $1,395/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $155 when you book by Feb-20-2019**
" The view and being in a small town. ..." - Joseph
Save $120 Photo of Cozy Apartment Rental in the Chianti Area
  • min $766/wk
  • max $1,195/wk
  • min $689/wk
  • max $1,076/wk
  • Min Stay: 7 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $120 when you book by Feb-20-2019**
" Enjoyed the villa and its location in the small town very much...." - Richard P
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 Feb-20-2019**
Save $391 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,059/wk
  • min $1,192/wk
  • max $1,668/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $391 when you book by Feb-20-2019**
" My wife and I had a wonderful stay at Machiavelli. The grounds and view of the countryside were exquisite. Our villa was a great mix of old world charm and modern ..." - Aaron
Save $146 Photo of Charming 14th Century Apartment in the Center of a Medieval Town in Tuscany
  • $1,458/wk
  • $1,312/wk
  • Min Stay: 7 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 2 bathrooms
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $146 when you book by Feb-20-2019**
" The restoration is very good quality. Most of the furnishings are Ikea so they are functional and attractive. Antiques and paintings add to the atmosphere of the p..." - Allan
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 Feb-20-2019**
" The people managing the property are first class. Very conscientious and helpful. ..." - Bo
Save $1,372 Photo of Chianti Classico Farmhouse with Stunning Views
  • min $4,323/wk
  • max $13,720/wk
  • min $3,891/wk
  • max $12,348/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 2 single bedrooms
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $1,372 when you book by Feb-20-2019**
" SPECTACULAR!..." - Linda
Save $324 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $1,888/wk
  • max $3,235/wk
  • min $1,699/wk
  • max $2,912/wk
  • Min Stay: 5 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $324 when you book by Feb-20-2019**
" Loved La Solaia, very cozy and comfortable and it was everything we hoped for and more. The location was excellent to surrounding areas and the views were to die f..." - John
Save $396 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • min $2,293/wk
  • max $3,963/wk
  • min $2,064/wk
  • max $3,567/wk
  • Min Stay: 5 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $396 when you book by Feb-20-2019**
" Terrific. ..." - Claudia
Save $2,021 Photo of Luxury Farmhouse in the Chianti Wine Region
  • min $13,109/wk
  • max $20,214/wk
  • min $11,798/wk
  • max $18,193/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 $2,021 when you book by Feb-20-2019**
" Wonderful...." - Jackie
Save $155 Photo of Walk To Small Town for Cappuccino in Tuscany
  • min $953/wk
  • max $1,550/wk
  • min $858/wk
  • max $1,395/wk
  • Min Stay: 7 days
Sleeps 5 to 6 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $155 when you book by Feb-20-2019**
" It was excellent. The pool was great, very clean and Sonia was very helpful when we arrived. ..." - David
Save $1,210 Photo of Tuscany Villa on a Hill Close to Florence
  • min $4,411/wk
  • max $6,371/wk
  • min $3,573/wk
  • max $5,161/wk
  • Min Stay: 7 days
Sleeps 8 to 11 people
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,210 when you book by Feb-20-2019**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
Save $1,470 Photo of Rural Woodland Tuscan villa with Pool and BBQ near Montaione
  • min $8,402/wk
  • max $14,702/wk
  • min $7,562/wk
  • max $13,232/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,470 when you book by Feb-20-2019**
Save $1,733 Photo of Luxury Chianti Villa Near a Small Town
  • min $11,375/wk
  • max $17,325/wk
  • min $10,238/wk
  • max $15,593/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,733 when you book by Feb-20-2019**
" What a lovely villa! The location was perfect to get away from the crowds of Florence. Such a beautiful setting amongst the olive trees and vineyards nearby...." - Cyndi
Save $248 Photo of Chianti Farmhouse on a Wine Estate
  • min $1,289/wk
  • max $2,483/wk
  • min $1,160/wk
  • max $2,235/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $248 when you book by Feb-20-2019**
" It is a beautiful setting for a relaxed vacation...." - ANNAMMA
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 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Feb-20-2019**
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
Save $570 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $4,032/wk
  • max $5,701/wk
  • min $3,629/wk
  • max $5,131/wk
  • Min Stay: 7 days
Sleeps 12 to 15 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $570 when you book by Feb-20-2019**
Save $221 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,512/wk
  • max $2,205/wk
  • min $1,361/wk
  • max $1,985/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $221 when you book by Feb-20-2019**
" We loved everything about our stay. Three couples stayed in Poggio 2. We were very comfortable--the 3 bedroom, 3 bath apartment was perfect. It was quiet and p..." - Mary
Save $170 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,071/wk
  • max $1,701/wk
  • min $964/wk
  • max $1,531/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $170 when you book by Feb-20-2019**
Save $256 Photo of Charming Apartment in Tuscany Perfect for a Family Holiday
  • min $2,063/wk
  • max $2,560/wk
  • min $1,857/wk
  • max $2,304/wk
  • Min Stay: 7 days
Sleeps 3 to 5 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $256 when you book by Feb-20-2019**
" The villa was very nice. Spacious and well appointed. The setting was beautiful. The villa itself was very close to a road that took some getting used to...." - alan
 
Displaying 1 to 30 of 179 villas

Following the old Chiantigiana road you see the heart of this region, including the northerly reaches of San Casciano and its environs and the Chianti Classico. What to do while in the Chianti? Eat, drink, and be merry. Towns like Panzano, Greve-in-Chianti, and Radda-in-Chianti---and all the wineries in between---are filled with gastronomic delights and a dizzying selection of wine shops. A wonderful place to bring your family or friends for an unforgettable Tuscan experience. With so much to do in the area, everyone in your group will love the area. View our Rental Villas in South Florence..