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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 180 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 Sep-30-2018**
" My family and I had an amazing stay at Poggio Antico. The villa was perfect for 6 adults, each of us had our own room and bathroom (and my parents specifically app..." - Rachael
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 Sep-30-2018**
" This was incredible villa and overall experience. The villa itself was more beautiful then the pictures portrayed, but the best part was the family that owned the..." - Thomas
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 Sep-30-2018**
" My family's experience was wonderful. Coffee on the terrace with a incredible view , the salt water pool and the most helpful owners in regards to directions, ..." - Brittania
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: 7 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 Sep-30-2018**
" We thoroughly enjoyed our two weeks in Villa Certaldo. We had stayed there 11 years ago and we enjoyed it more this time than we did the first and that is saying ..." - Jim
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 7 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $206 when you book by Sep-30-2018**
" Perfect. ..." - Mario
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 Sep-30-2018**
" 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 $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: 7 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 Sep-30-2018**
" Wonderful property. So serene and scenic. Easy to unwind and relax yet close to many exciting places to visit..." - Steven
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: 7 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 Sep-30-2018**
" Beautiful views of the countryside. Very Tuscan rural villa. Quiet and restful place...." - Genevieve
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 Sep-30-2018**
" It was a wonderful stay. The home was very spacious. We loved being right next to the adorable town of Barberino Val d'Elsa. The gated entry was a plus sinc..." - Erinn
Save $878 Photo of Family Friendly Villa Rental in Tuscany with Pool
  • min $1,785/wk
  • max $8,777/wk
  • min $1,607/wk
  • max $7,899/wk
  • Min Stay: 7 days
Sleeps 15 people
  • 1 single bedrooms
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $878 when you book by Sep-30-2018**
" Great week...." - Maria
Save $2,058 Photo of Large Luxury Villa Rental in the Chianti with Spectacular Views
  • min $11,832/wk
  • max $20,583/wk
  • min $10,649/wk
  • max $18,525/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $2,058 when you book by Sep-30-2018**
" One of the most enjoyable and memorable family experiences we ever had!..." - Louis
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 Sep-30-2018**
" 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 $174 Photo of Tuscan Apartment in Historic Castle
  • min $957/wk
  • max $1,738/wk
  • min $861/wk
  • max $1,564/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $174 when you book by Sep-30-2018**
Save $971 Photo of Beautiful Tuscany Villa for a Large Group with Spectacular Views
  • min $4,481/wk
  • max $9,708/wk
  • min $4,033/wk
  • max $8,737/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $971 when you book by Sep-30-2018**
" Our experience at Villa Pucci was absolute perfection! The house and view are spectacular. ..." - Amy
Save $245 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,512/wk
  • max $2,450/wk
  • min $1,361/wk
  • max $2,205/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $245 when you book by Sep-30-2018**
" 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 $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 Sep-30-2018**
" Beautiful place for our group. Lovely big villa and lovely grounds. Remote, so needed rental scooters and bikes to explore nearby towns. Pool was a hit. ..." - Anne
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 Sep-30-2018**
" Delightful! We had come from Paris. Lucolena was the perfect contrast to a busy city. Loved the villa. We enjoyed the nearby towns, Greve and Dudda. We enjoye..." - Dennis
Save $155 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,545/wk
  • min $630/wk
  • max $1,391/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $155 when you book by Sep-30-2018**
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 Sep-30-2018**
" It is a beautiful setting for a relaxed vacation...." - ANNAMMA
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 Sep-30-2018**
" 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 $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 Sep-30-2018**
" Lovely, relaxing stay with easy access to onsite property managers. ..." - Katie
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 Sep-30-2018**
" Amazing!! From the moment we arrived it felt like heaven on earth. The villa is beautiful. We had plenty of room and the facilities were immaculate. The pool was t..." - Nichola
Save $313 Photo of Tuscan Villa with a Private Pool in a Village
  • min $615/wk
  • max $3,127/wk
  • min $554/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 Sep-30-2018**
" Outstanding and memorable experience for all of us...." - Bruce
Save $266 Photo of Tuscany Vacation Villa
  • min $1,541/wk
  • max $2,661/wk
  • min $1,387/wk
  • max $2,395/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
  • Air Conditioning
** Save up to $266 when you book by Sep-30-2018**
" It was wonderful. ..." - Cathie
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 Sep-30-2018**
" A wonderful place to relax after travelling non stop for a couple of weeks. A chance to unpack and spread out in such a beautiful part of the world. The refurbishm..." - Murray
Save $1,370 Photo of Villas for Rent on Large Estate Near Certaldo
  • min $8,036/wk
  • max $13,700/wk
  • min $7,232/wk
  • max $12,330/wk
  • Min Stay: 7 days
Sleeps 24 to 28 people
  • 12 double bedrooms
  • 13 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,370 when you book by Sep-30-2018**
" Overall, it was positive...." - Cheryl
Save $404 Photo of Tuscany Villa within Walking Distance to Greve
  • min $1,890/wk
  • max $4,044/wk
  • min $1,701/wk
  • max $3,640/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $404 when you book by Sep-30-2018**
" Enjoyable ..." - Deborah
Save $4,487 Photo of Castle Rental in Tuscany, Montespertoli (Chianti Area)
  • min $23,519/wk
  • max $44,865/wk
  • min $21,167/wk
  • max $40,379/wk
  • Min Stay: 7 days
Sleeps 80 to 120 people
  • 1 single bedrooms
  • 42 double bedrooms
  • 35 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $4,487 when you book by Sep-30-2018**
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 Sep-30-2018**
Save $308 Photo of Chianti Farmhouse on a Wine Estate
  • min $1,625/wk
  • max $3,081/wk
  • min $1,463/wk
  • max $2,773/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $308 when you book by Sep-30-2018**
" Excellent. Beautiful house and property...." - Gary
 
Displaying 1 to 30 of 180 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..