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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 $909 Photo of Villa Rental Chianti Tuscany Near Florence
  • min $2,409/wk
  • max $4,543/wk
  • min $1,734/wk
  • max $3,634/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 $909 when you book by Oct-31-2018**
" 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 $653 Photo of Farmhouse Rental Near Certaldo, Tuscany
  • min $2,283/wk
  • max $3,264/wk
  • min $1,826/wk
  • max $2,611/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 $653 when you book by Oct-31-2018**
" 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 Oct-31-2018**
" It was an amazing experience. The property was lovely and we used the pool daily...." - Linda
Save $1,245 Photo of Tuscany Villa Rental in Chianti
  • min $1,888/wk
  • max $3,558/wk
  • min $1,227/wk
  • max $2,313/wk
  • Min Stay: 5 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,245 when you book by Oct-31-2018**
" The experience was amazing. It was two perfect weeks...." - Michael
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 Oct-31-2018**
" 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 $1,601 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
  • min $2,077/wk
  • max $3,559/wk
  • min $1,142/wk
  • max $1,957/wk
  • Min Stay: 5 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,601 when you book by Oct-31-2018**
" We loved it and would stay there each time we go to Tuscany! The villa could not have been nicer. Elizabeth was fantastic. The outside area was far better than we ..." - Ronald
Save $1,387 Photo of Family-Friendly Villa Rental in Tuscany with Pool
  • min $2,084/wk
  • max $3,963/wk
  • min $1,355/wk
  • max $2,576/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 $1,387 when you book by Oct-31-2018**
" Beautiful views of the countryside. Very Tuscan rural villa. Quiet and restful place...." - Genevieve
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 Oct-31-2018**
" Enjoyable ..." - Deborah
Save $539 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $1,663/wk
  • max $2,695/wk
  • min $1,331/wk
  • max $2,156/wk
  • Min Stay: 7 days
Sleeps 6 to 7 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
** Save up to $539 when you book by Oct-31-2018**
" 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 $1,088 Photo of Family-Friendly Tuscan Villa with Private Pool
  • min $2,157/wk
  • max $5,442/wk
  • min $1,726/wk
  • max $4,353/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,088 when you book by Oct-31-2018**
" Fabulous...." - Tom
Save $2,156 Photo of Villa Rental in Tuscany, Gambassi Terme
  • min $7,470/wk
  • max $10,782/wk
  • min $5,976/wk
  • max $8,626/wk
  • Min Stay: 3 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $2,156 when you book by Oct-31-2018**
" 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 $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 Oct-31-2018**
" 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 $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 Oct-31-2018**
" 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 $339 Photo of Holiday Accommodation in Chianti
  • min $848/wk
  • max $1,695/wk
  • min $678/wk
  • max $1,356/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 $339 when you book by Oct-31-2018**
" It was an amazing vacation with our family in this beautiful setting. Our host Leonardo was extremely gracious and very accommodating...." - Diana
Save $1,162 Photo of Luxury Chianti Villa on a Wine Estate
  • $11,622/wk
  • $10,460/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,162 when you book by Oct-31-2018**
" Exceptional villa...." - Jerry
Save $339 Photo of Holiday Accommodation in Chianti
  • min $848/wk
  • max $1,695/wk
  • min $678/wk
  • max $1,356/wk
  • Min Stay: 7 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $339 when you book by Oct-31-2018**
" Fantastic place with beautiful views, very secluded and quiet. Great and very large covered outdoor patio...." - Liz
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 Oct-31-2018**
" 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 $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 Oct-31-2018**
" 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 $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 Oct-31-2018**
" It was wonderful and we would recommend it to anyone...." - Dolores
Save $1,394 Photo of Tuscany Accommodation Within Walking Distance of Town
  • min $4,435/wk
  • max $6,969/wk
  • min $3,548/wk
  • max $5,575/wk
  • Min Stay: 7 days
Sleeps 12 to 15 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
** Save up to $1,394 when you book by Oct-31-2018**
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $700/wk
  • max $1,617/wk
  • min $630/wk
  • max $1,455/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Oct-31-2018**
" Wonderful. A magnificent building in beautiful countryside. We rented 5 units - all in the out-buildings. I entered the same comments for all 5 units. ..." - Michael
Save $677 Photo of Tuscany Villa within Walking Distance to Greve
  • min $1,671/wk
  • max $3,387/wk
  • min $1,337/wk
  • max $2,710/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $677 when you book by Oct-31-2018**
" In very good condition. A real retreat with a fantastic view..." - Andrew
Save $2,136 Photo of Beautiful Tuscany Villa for a Large Group with Spectacular Views
  • min $4,929/wk
  • max $10,679/wk
  • min $3,943/wk
  • max $8,543/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 $2,136 when you book by Oct-31-2018**
" Our experience at Villa Pucci was absolute perfection! The house and view are spectacular. ..." - Amy
Save $214 Photo of Pleasant Apartment in San Barberino Val d'Elsa
  • min $740/wk
  • max $1,068/wk
  • min $592/wk
  • max $854/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 $214 when you book by Oct-31-2018**
" We had a amazing time in Tuscany and loved our little villa!..." - Melissa
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 Oct-31-2018**
" 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 $4,447 Photo of Luxury Farmhouse in the Chianti Wine Region
  • min $14,419/wk
  • max $22,235/wk
  • min $11,535/wk
  • max $17,788/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 $4,447 when you book by Oct-31-2018**
" Wonderful...." - Jackie
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 Oct-31-2018**
" Outstanding and memorable experience for all of us...." - Bruce
Save $1,571 Photo of Villa Rental in Tuscany, San Donato in Poggio
  • min $5,236/wk
  • max $7,854/wk
  • min $4,189/wk
  • max $6,283/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,571 when you book by Oct-31-2018**
Save $3,881 Photo of Historic Tuscan Villa on a Wine Estate in the Chianti Region
  • min $10,320/wk
  • max $19,407/wk
  • min $8,256/wk
  • max $15,526/wk
  • Min Stay: 7 days
Sleeps 13 to 14 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,881 when you book by Oct-31-2018**
" Villa Carmina is wonderful. There were 13 adults in our party and the villa easily accommodated a group of that size. ..." - Bruce
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 Oct-31-2018**
 
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..