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Black Friday Specials - Villas Up to 50 Percent Off

Hurry and take advantage of discounts up to 50% off at some of our top villas valid through 12-31-2019! 

Displaying 1 to 15 of 15 villas
    Save $1,058 Photo of Cozy Tuscan Villa near Montepulciano
    • min $5,041/wk
    • max $10,580/wk
    • min $4,537/wk
    • max $9,522/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 $1,058 when you book by May-31-2020**
    " There were 13 of us, 8 adults and 5 children ages 6 to 10. All had a great time and there was plenty of room for all. The adults particularly enjoyed sitting on th..." - Michael
    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: 4 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 May-31-2020**
    " We loved our stay! The location is perfect and very peaceful. With a car everything is close and accessible. The villa was big for our family of 4 but we loved it...." - Pia
    Save $327 Photo of Farmhouse Rental Near Certaldo, Tuscany
    • min $2,440/wk
    • max $3,267/wk
    • min $2,196/wk
    • max $2,940/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 $327 when you book by May-31-2020**
    " Our overall experience staying at Donatella was simply fantastic. The villa is just beautiful. The accommodations were so nice and very comfortable. The views were..." - George
    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: 4 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 May-31-2020**
    " Our experience was very soul-refreshing with the family at La Solaia. We enjoyed the location and the home. The kitchen was stocked with enough basic equipment to ..." - Dana
    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: 4 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 May-31-2020**
    " Wonderful all around!..." - Cinnamon
    Save $340 Photo of Apartment in Siena Overlooking the Famous Piazza del Campo
    • min $2,615/wk
    • max $3,399/wk
    • min $2,354/wk
    • max $3,059/wk
    • Min Stay: 3 days
    Sleeps 2 people
    • 1 double bedrooms
    • 1 bathrooms
    ** Save up to $340 when you book by May-31-2020**
    " Very good...." - Kenneth
    Save $718 Photo of Lakeview Tuscan countryside property has pool, gardens, wine cellar!
    • min $5,250/wk
    • max $7,175/wk
    • min $4,725/wk
    • max $6,458/wk
    • Min Stay: 7 days
    Sleeps 10 people
    • 5 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $718 when you book by May-31-2020**
    Save $1,294 Photo of Rustic Countryside Villa with Pool near San Casciano dei Bagni
    • min $7,106/wk
    • max $12,938/wk
    • min $6,395/wk
    • max $11,644/wk
    • Min Stay: 7 days
    Sleeps 14 people
    • 7 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $1,294 when you book by May-31-2020**
    " Wonderful - We stayed at Villa Orcia with 10 adults and there was plenty of room for everyone. Patrizia is extremely helpful...." - Renee
    Save $496 Photo of Tuscany Villa with Four Bedrooms all with En Suite Baths
    • min $3,000/wk
    • max $4,961/wk
    • min $2,700/wk
    • max $4,465/wk
    • Min Stay: 7 days
    Sleeps 8 to 10 people
    • 4 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Maid Service
    ** Save up to $496 when you book by May-31-2020**
    " Truly excellent. The only thing that could have been better would have been the weather...." - James
    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: 4 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 May-31-2020**
    " Overall, it was positive...." - Cheryl
    Save $752 Photo of Beautiful Estate for Rent with Two Pools Near Certaldo
    • min $4,369/wk
    • max $7,521/wk
    • min $3,932/wk
    • max $6,769/wk
    • Min Stay: 4 days
    Sleeps 12 to 14 people
    • 6 double bedrooms
    • 7 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Maid Service
    ** Save up to $752 when you book by May-31-2020**
    " It was awesome! And meeting Elizabeth and Adi, the owners, was a highlight! Loved them and hiking all over the property!..." - Anne
    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 May-31-2020**
    Save $490 Photo of Villa near Montalcino
    • min $3,675/wk
    • max $4,900/wk
    • min $3,308/wk
    • max $4,410/wk
    • Min Stay: 7 days
    Sleeps 6 people
    • 3 double bedrooms
    • 2 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    ** Save up to $490 when you book by May-31-2020**
    " It was like our own villa. The owners were so helpful in making everything work and we enjoyed our holiday. The sun room was a special place. We set it up as o..." - Geoff
    Save $307 Photo of Villa in Tuscany Near Certaldo and the Chianti Region
    • min $1,794/wk
    • max $3,073/wk
    • min $1,615/wk
    • max $2,766/wk
    • Min Stay: 4 days
    Sleeps 6 to 7 people
    • 3 double bedrooms
    • 3 bathrooms
    • Swimming Pool
    • Washing Machine
    • Maid Service
    ** Save up to $307 when you book by May-31-2020**
    " Fantastic, better than our high expectations!..." - Harri
    Save $683 Photo of Villa Rental in Tuscany, Cortona
    • min $4,480/wk
    • max $6,825/wk
    • min $4,032/wk
    • max $6,143/wk
    • Min Stay: 7 days
    Sleeps 10 people
    • 5 double bedrooms
    • 4 bathrooms
    • Independent House
    • Swimming Pool
    • Washing Machine
    • Air Conditioning
    ** Save up to $683 when you book by May-31-2020**
     
    Displaying 1 to 15 of 15 villas