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Under the Tuscan Sun Villas and Vacation Rentals

You've dreamt of the rolling Tuscan hills; glasses of ruby-red Classico; villas framed with the orange glow of the setting sun; medieval hill towns outlined on the horizon... So come experience Italian life at its best, under the Tuscan sun. 

Displaying 31 to 60 of 59 villas
Save $3,851 Photo of Private luxury villa near Florence with pool, tennis court, beautiful gardens, spectacular views.
  • min $17,503/wk
  • max $38,505/wk
  • min $15,753/wk
  • max $34,655/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,851 when you book by Jan-20-2019**
Save $518 Photo of Chianti Tuscany Villa Rental, Near Siena
  • min $2,451/wk
  • max $5,181/wk
  • min $2,206/wk
  • max $4,663/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $518 when you book by Jan-20-2019**
" We had a wonderful time at the property..." - Leo
Save $1,091 Photo of Historic 16th Century Villa in Tuscany with  Private Pool and Shared Tennis Court
  • min $6,767/wk
  • max $10,905/wk
  • min $6,090/wk
  • max $9,815/wk
  • Min Stay: 7 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Independent House
  • Swimming Pool
  • Maid Service
** Save up to $1,091 when you book by Jan-20-2019**
" Of all the lovely places I've been, it's the one I most want to return to. Sooo relaxing--because of the peaceful, beautiful surroundings, the beauty of th..." - Anne
Save $729 Photo of Tuscany Villa near Siena with Private Pool
  • min $1,868/wk
  • max $7,293/wk
  • min $1,681/wk
  • max $6,564/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 2 single bedrooms
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $729 when you book by Jan-20-2019**
" Very good. The property management had lots of cheeses, meats, bread and wine for us upon arrival. Both kitchens were well stocked with glassware, dishes, pots an..." - Johnnie Lynn
Save $588 Photo of Charming Villa with Pool in Tuscany
  • min $2,801/wk
  • max $5,881/wk
  • min $2,521/wk
  • max $5,293/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 $588 when you book by Jan-20-2019**
" Very Good. A little too far from grocery store and Florence...." - Mary
Save $1,323 Photo of Large Villa in Chianti Hills Close to Florence
  • min $8,555/wk
  • max $13,228/wk
  • min $7,699/wk
  • max $11,905/wk
  • Min Stay: 7 days
Sleeps 19 people
  • 1 single bedrooms
  • 9 double bedrooms
  • 9 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,323 when you book by Jan-20-2019**
" It was a wonderful place to stay. Paolo, Beatrice and all were very helpful. ..." - Jean
Save $735 Photo of Lovely Villa with Countryside Views of Tuscany
  • min $3,493/wk
  • max $7,349/wk
  • min $3,144/wk
  • max $6,614/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $735 when you book by Jan-20-2019**
" Perfect!..." - Michal
Save $1,160 Photo of Large Villa in the Chianti Hills Close to Florence
  • min $7,616/wk
  • max $11,603/wk
  • min $6,854/wk
  • max $10,443/wk
  • Min Stay: 7 days
Sleeps 14 people
  • 7 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,160 when you book by Jan-20-2019**
" Amazing. We has a wonderful time. ..." - Tim
Save $448 Photo of Villa Near Cortona with a Private Pool
  • min $3,003/wk
  • max $4,480/wk
  • min $2,703/wk
  • max $4,032/wk
  • Min Stay: 7 days
Sleeps 9 people
  • 1 single bedrooms
  • 4 double bedrooms
  • 4 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $448 when you book by Jan-20-2019**
" We loved our villa! The home was a vision of what, in our minds, Tuscany would look like. It was so comfortable and perfect for our stay. Louisa was darling and ..." - Cindy
Save $2,296 Photo of Large Resort Estate in Umbria Ideal for Large Groups
  • min $15,122/wk
  • max $22,963/wk
  • min $13,610/wk
  • max $20,667/wk
  • Min Stay: 3 days
Sleeps 26 people
  • 13 double bedrooms
  • 13 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,296 when you book by Jan-20-2019**
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 Jan-20-2019**
" Everything was fine...." - William
Save $1,079 Photo of Beautiful Hilltop Villa in Tuscany with Spectacular Views
  • min $5,220/wk
  • max $10,785/wk
  • min $4,698/wk
  • max $9,707/wk
  • Min Stay: 7 days
Sleeps 13 to 18 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,079 when you book by Jan-20-2019**
" Our group cherishes relationships and therefore thoughtfulness, condsideration and a desire to serve are a valuable component of our friendships. Upon meeting Ale..." - Mark
Save $378 Photo of Charming Cottage for Two Couples or Small Family Near Cortona
  • $3,780/wk
  • $3,402/wk
  • Min Stay: 7 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $378 when you book by Jan-20-2019**
" It was wonderful. It is very comfortable and the views are magnificent. The landscaping is well done and interesting...." - Richard
Save $1,148 Photo of Large Villa in Tuscany with Two Pools
  • min $9,100/wk
  • max $11,480/wk
  • min $8,190/wk
  • max $10,332/wk
  • Min Stay: 7 days
Sleeps 20 people
  • 10 double bedrooms
  • 10 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,148 when you book by Jan-20-2019**
" Our expectations were exceeded. We rented the villa for the month of October 2015. The property manager, is a master of customer service and charm...." - Alice
Save $1,688 Photo of Villa Rental near Florence with Pool and Fruit Orchard
  • min $5,625/wk
  • max $16,875/wk
  • min $5,063/wk
  • max $15,188/wk
  • Min Stay: 7 days
Sleeps 8 to 10 people
  • 4 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,688 when you book by Jan-20-2019**
" Fantastic. Beyond our expectations...." - Maggie
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 Jan-20-2019**
" In very good condition. A real retreat with a fantastic view..." - Andrew
Save $910 Photo of Self Catering Accommodation in Tuscany
  • min $4,901/wk
  • max $9,102/wk
  • min $4,411/wk
  • max $8,192/wk
  • Min Stay: 7 days
Sleeps 18 people
  • 9 double bedrooms
  • 7 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $910 when you book by Jan-20-2019**
" Overall experience was wonderful. Gabriella, the manager, was well-informed and provided great insight as to local restaurants, local markets, local stores and tr..." - Dorothy
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 Jan-20-2019**
" Amazing! Staying here was like being in paradise. ..." - Cassandra
Save $672 Photo of Exclusive  Hilltop  Medieval  Villa  Features  Modern  Comforts,  Panoramic  Sea  Views,  Garden,  Pool  and  Jacuzzi  in  Pistoia,  Tuscany
  • min $2,731/wk
  • max $6,721/wk
  • min $2,458/wk
  • max $6,049/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $672 when you book by Jan-20-2019**
Save $653 Photo of Villa for a Group Near Trasimeno Lake
  • min $4,107/wk
  • max $6,534/wk
  • min $3,696/wk
  • max $5,881/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $653 when you book by Jan-20-2019**
Save $1,400 Photo of Rural Lucca Villa with Pool and Spectacular Views
  • min $8,752/wk
  • max $14,002/wk
  • min $7,877/wk
  • max $12,602/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,400 when you book by Jan-20-2019**
Save $902 Photo of Tuscan Farmhouse with Private Pool and Beautiful Views
  • min $5,880/wk
  • max $9,016/wk
  • min $5,292/wk
  • max $8,114/wk
  • Min Stay: 7 days
Sleeps 12 people
  • 6 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $902 when you book by Jan-20-2019**
Save $2,685 Photo of Villa Rental Tuscany
  • min $4,900/wk
  • max $7,140/wk
  • min $3,749/wk
  • max $5,462/wk
  • Min Stay: 4 days
Sleeps 16 people
  • 8 double bedrooms
  • 8 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $2,685 when you book by Jan-20-2019**
" Adequate space for a large group - wonderful views and ability to walk around. The manager at the reception was wonderful, efficient and accommodating...." - Sumaya
Save $600 Photo of Tuscany Villa Near Florence
  • min $2,000/wk
  • max $6,000/wk
  • min $1,800/wk
  • max $5,400/wk
  • Min Stay: 7 days
Sleeps 8 people
  • 4 double bedrooms
  • 4 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $600 when you book by Jan-20-2019**
" The property is gorgeous and nicely furnished...." - Deann
Save $2,199 Photo of Luxury Tuscany Villa Near Lucca and Walking Distance to a Small Village
  • $21,994/wk
  • $19,795/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 $2,199 when you book by Jan-20-2019**
" The villa was spectacular, even better than the photos. The grounds and surrounding areas were beautiful. It has been recently renovated and the owner spared no ..." - Elyce
Save $3,857 Photo of Renovated Farmhouse Villa in Southern Tuscany for Families
  • min $16,240/wk
  • max $20,300/wk
  • min $13,154/wk
  • max $17,357/wk
  • Min Stay: 7 days
Sleeps 11 to 13 people
  • 1 single bedrooms
  • 6 double bedrooms
  • 6 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $3,857 when you book by Jan-20-2019**
Save $1,094 Photo of Beautiful Historic Villa Near Monteriggioni in Tuscany
  • min $8,629/wk
  • max $10,935/wk
  • min $7,766/wk
  • max $9,842/wk
  • Min Stay: 7 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $1,094 when you book by Jan-20-2019**
" I would and already have recommended the villa to anyone. My experience with your firm was excellent. When I return to Tuscany I intend to stay at the same locatio..." - Hal
Save $1,276 Photo of Large Villa Rental near Vorno, Lucca with Air Conditioning
  • $12,759/wk
  • $11,483/wk
  • Min Stay: 7 days
Sleeps 10 people
  • 5 double bedrooms
  • 5 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $1,276 when you book by Jan-20-2019**
" Pool area, kitchen, comfortable furnishings...." - Colleen
Save $1,050 Photo of Gorgeous Toscana Villa with pools, private garden and views
  • min $6,126/wk
  • max $10,502/wk
  • min $5,513/wk
  • max $9,452/wk
  • Min Stay: 7 days
Sleeps 10 to 12 people
  • 5 double bedrooms
  • 5 bathrooms
  • Swimming Pool
  • Washing Machine
  • Air Conditioning
** Save up to $1,050 when you book by Jan-20-2019**
 
Displaying 31 to 60 of 59 villas