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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 $416 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,190/wk
  • max $4,130/wk
  • min $1,774/wk
  • max $3,717/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 $416 when you book by Dec-15-2018**
" 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 Dec-20-2018**
" 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 $1,888/wk
  • max $3,558/wk
  • min $1,699/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 Dec-20-2018**
" 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
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $297 when you book by Dec-20-2018**
" 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 $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 Dec-20-2018**
" The view and being in a small town. ..." - Joseph
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 Dec-20-2018**
" 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 $2,084/wk
  • max $3,963/wk
  • min $1,876/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 Dec-20-2018**
" Terrific. ..." - Claudia
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 Dec-20-2018**
" Overall we had a good week. ..." - Phil
Save $313 Photo of Tuscan Villa with a Private Pool in a Village
  • min $644/wk
  • max $3,127/wk
  • min $580/wk
  • max $2,814/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $313 when you book by Dec-20-2018**
" We stayed there for a summer in 2009 it was a wonderful experience then and again this visit. We know the rhythm of the village so enjoy all it has to offer..." - Joy
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 Dec-20-2018**
" The people managing the property are first class. Very conscientious and helpful. ..." - Bo
Save $504 Photo of Two Chianti Farmhouses for Large Group on a Wine Estate
  • min $2,651/wk
  • max $5,041/wk
  • min $2,386/wk
  • max $4,537/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $504 when you book by Dec-20-2018**
" Overall it was a great stay. Rooms were perfect for what we needed. Views are amazing. It is good for big groups of 10 or more. Big upstairs meeting room, plen..." - Jeff
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 Dec-20-2018**
" Fantastic! Just as great as I thought it would be! The outdoor pool seating areas were amazing...." - Mary Ann
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 Dec-20-2018**
" 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 $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 Dec-20-2018**
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 Dec-20-2018**
" 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 $1,313 Photo of Chianti Classico Farmhouse with Stunning Views
  • min $4,138/wk
  • max $13,132/wk
  • min $3,724/wk
  • max $11,819/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 $1,313 when you book by Dec-20-2018**
" SPECTACULAR!..." - Linda
Save $206 Photo of Tuscany Apartment in a Castle Hamlet Close to Florence
  • min $1,471/wk
  • max $2,059/wk
  • min $1,324/wk
  • max $1,853/wk
  • Min Stay: 7 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Maid Service
** Save up to $206 when you book by Dec-20-2018**
" 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 $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 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $154 when you book by Dec-20-2018**
" It was an amazing vacation with our family in this beautiful setting. Our host Leonardo was extremely gracious and very accommodating...." - Diana
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 Dec-20-2018**
" 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 $525 Photo of Traditional Tuscan House West of Florence
  • min $2,976/wk
  • max $5,251/wk
  • min $2,678/wk
  • max $4,726/wk
  • Min Stay: 7 days
Sleeps 7 to 8 people
  • 1 single bedrooms
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $525 when you book by Dec-20-2018**
" My clients loved the property! They spent many hours visiting in the kitchen while they cooked...." - Linda
Save $300 Photo of Tuscany Villa with Private Pool
  • min $1,587/wk
  • max $2,999/wk
  • min $1,428/wk
  • max $2,699/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $300 when you book by Dec-20-2018**
" The property was great but rather far from town...." - Betty
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 Dec-20-2018**
Save $2,021 Photo of Luxury Farmhouse in the Chianti Wine Region
  • min $13,108/wk
  • max $20,214/wk
  • min $11,797/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 Dec-20-2018**
" Wonderful...." - Jackie
Save $308 Photo of Tuscany Villa within Walking Distance to Greve
  • min $1,519/wk
  • max $3,079/wk
  • min $1,367/wk
  • max $2,771/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $308 when you book by Dec-20-2018**
" In very good condition. A real retreat with a fantastic view..." - Andrew
Save $229 Photo of Apartment Rental in Tuscany, San Polo
  • min $1,185/wk
  • max $2,294/wk
  • min $1,067/wk
  • max $2,065/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $229 when you book by Dec-20-2018**
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 Dec-20-2018**
" Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
Save $714 Photo of Villa Rental in Tuscany, San Donato in Poggio
  • min $4,760/wk
  • max $7,140/wk
  • min $4,284/wk
  • max $6,426/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $714 when you book by Dec-20-2018**
Save $637 Photo of Tuscany Villa on a Hill Close to Florence
  • min $4,411/wk
  • max $6,371/wk
  • min $3,970/wk
  • max $5,734/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 $637 when you book by Dec-20-2018**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
Save $279 Photo of Tuscany Farmhouse Close to a Castle
  • min $1,120/wk
  • max $2,793/wk
  • min $1,008/wk
  • max $2,514/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $279 when you book by Dec-20-2018**
" This location is perfectly situated for all the day trips we had planned, from Cinque Terre to Siena. ..." - Sadia
Save $200 Photo of Tuscany Apartment Near Florence with Restaurant
  • min $1,050/wk
  • max $2,000/wk
  • min $945/wk
  • max $1,800/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $200 when you book by Dec-20-2018**
" Very good...." - Leigh
 
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..