Suitcase

Your Suitcase contains your favorite villas and details of your upcoming trip. Sign up to use this feature.
Rated Excellent By Trip Advisor

Quick Filter

Travelers
Arrival Date
Departure Date
Max Price per Week

Montespertoli (Chianti Area) Villas and Vacation Rentals

 

Displaying 1 to 30 of 37 villas
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 $369 Photo of Tuscan Apartment in Historic Castle
  • min $809/wk
  • max $1,844/wk
  • min $647/wk
  • max $1,475/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $369 when you book by Oct-31-2018**
" We thoroughly enjoyed our stay and the property was very well-maintained. We would recommend staying here to others. We quickly realized, however, that some of the..." - Wendy
Save $292 Photo of Tuscan Apartment in Historic Castle
  • min $855/wk
  • max $1,459/wk
  • min $684/wk
  • max $1,167/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $292 when you book by Oct-31-2018**
" We loved everything about it, the architecture is wonderful, the grounds are like heaven. I would like to think the people-staff are the best, and we are going ba..." - Barbara
Save $356 Photo of Tuscan Apartment in Historic Castle
  • min $770/wk
  • max $1,779/wk
  • min $616/wk
  • max $1,423/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $356 when you book by Oct-31-2018**
" Wonderful. A magnificent castle with out-buildings in beautiful countryside. We rented 5 units - all in the out-buildings. I entered the same comments for all 5 ..." - Michael
Save $226 Photo of Tuscan Apartment in Historic Castle
  • min $568/wk
  • max $1,132/wk
  • min $454/wk
  • max $906/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $226 when you book by Oct-31-2018**
Save $191 Photo of Tuscan Apartment in Historic Castle
  • min $840/wk
  • max $1,911/wk
  • min $756/wk
  • max $1,720/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $191 when you book by Oct-31-2018**
" It was comfortable, clean, and conveniently located. ..." - Misty
Save $275 Photo of Tuscan Apartment in Historic Castle
  • min $693/wk
  • max $1,377/wk
  • min $554/wk
  • max $1,102/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $275 when you book by Oct-31-2018**
Save $469 Photo of Tuscan Apartment in Historic Castle
  • min $1,001/wk
  • max $2,346/wk
  • min $801/wk
  • max $1,877/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $469 when you book by Oct-31-2018**
" We loved it. We were 6 woman so we bought local fare and cooked in our big kitchen. ..." - Alice Celine
Save $323 Photo of Tuscan Apartment in Historic Castle
  • min $770/wk
  • max $1,617/wk
  • min $616/wk
  • max $1,294/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $323 when you book by Oct-31-2018**
" We liked the gardens and the castle next door, the views of the country, and the quietness. We slept well, but in the summer it's warm, and there is no A/C. A ..." - Carlos
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 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Oct-31-2018**
Save $304 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $942/wk
  • max $1,519/wk
  • min $753/wk
  • max $1,215/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $304 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 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
  • Air Conditioning
** Save up to $162 when you book by Oct-31-2018**
" The location was very good. Easy driving to some of the towns we wanted to visit, such as Pisa, Lucca and Siena. The beds were comfortable and the villa was roomy..." - Cheryl
Save $133 Photo of Tuscan Apartment in Historic Castle
  • min $653/wk
  • max $1,326/wk
  • min $588/wk
  • max $1,193/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $133 when you book by Oct-31-2018**
Save $176 Photo of Tuscan Apartment in Historic Castle
  • min $770/wk
  • max $1,764/wk
  • min $693/wk
  • max $1,588/wk
  • Min Stay: 3 days
Sleeps 5 people
  • 1 single bedrooms
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $176 when you book by Oct-31-2018**
Save $259 Photo of Tuscan Apartment in Historic Castle
  • min $585/wk
  • max $1,294/wk
  • min $468/wk
  • max $1,035/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $259 when you book by Oct-31-2018**
" Spacious apartment, clean and appropriately furnished. The bedroom is very good and comfortable, as is the bathroom...." - Real
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 Oct-31-2018**
Save $292 Photo of Tuscan Apartment in Historic Castle
  • min $809/wk
  • max $1,459/wk
  • min $647/wk
  • max $1,167/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $292 when you book by Oct-31-2018**
" We had a delightful time at the castle. The apartment was lovely and well maintained. The castle was very scenic...." - Joan
Save $157 Photo of Tuscan Apartment in Historic Castle
  • min $744/wk
  • max $1,568/wk
  • min $670/wk
  • max $1,411/wk
  • Min Stay: 3 days
Sleeps 3 to 4 people
  • 1 single bedrooms
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Oct-31-2018**
Save $356 Photo of Tuscan Apartment in Historic Castle
  • min $970/wk
  • max $1,779/wk
  • min $776/wk
  • max $1,423/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $356 when you book by Oct-31-2018**
" Beautiful, large castle in a picture perfect location that seemed like something out of a Tuscan fantasy. ..." - Deborah
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 Oct-31-2018**
" We'll be back...." - Tammy
Save $259 Photo of Tuscan Apartment in Historic Castle
  • min $585/wk
  • max $1,294/wk
  • min $468/wk
  • max $1,035/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $259 when you book by Oct-31-2018**
Save $174 Photo of Tuscan Apartment in Historic Castle
  • min $882/wk
  • max $1,738/wk
  • min $794/wk
  • max $1,564/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $174 when you book by Oct-31-2018**
" We absolutely loved our time at Il Castello 27! Our family loved the property and the people that worked there were so friendly and helpful!..." - Sharon
Save $345 Photo of Tuscan Apartment in Historic Castle
  • min $976/wk
  • max $1,725/wk
  • min $781/wk
  • max $1,380/wk
  • Min Stay: 3 days
Sleeps 2 to 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $345 when you book by Oct-31-2018**
" Excellent. Relaxing. Different. One of the highlights was 25 school childen fom New Zealand staying overnight. Sharing a bus with them and then dinner later. They ..." - Edward
Save $394 Photo of Tuscan Apartment in Historic Castle
  • min $1,008/wk
  • max $1,969/wk
  • min $806/wk
  • max $1,575/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 3 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $394 when you book by Oct-31-2018**
" Very good. However, it was 104 most days and didn't cool off much at night. Good home base for day trips...." - Kelly
Save $297 Photo of Tuscan Apartment in Historic Castle
  • min $872/wk
  • max $1,485/wk
  • min $698/wk
  • max $1,188/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $297 when you book by Oct-31-2018**
Save $174 Photo of Tuscan Apartment in Historic Castle
  • min $1,015/wk
  • max $1,738/wk
  • min $914/wk
  • max $1,564/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $174 when you book by Oct-31-2018**
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 Oct-31-2018**
Save $497 Photo of Tuscan Apartment in Historic Castle
  • min $1,263/wk
  • max $2,487/wk
  • min $1,010/wk
  • max $1,990/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $497 when you book by Oct-31-2018**
" Good...." - Randee
Save $262 Photo of Tuscan Apartment in Historic Castle
  • min $761/wk
  • max $1,311/wk
  • min $609/wk
  • max $1,049/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $262 when you book by Oct-31-2018**
" Ambiance. Staff was very good...." - Will
Save $157 Photo of Tuscan Apartment in Historic Castle
  • min $931/wk
  • max $1,568/wk
  • min $838/wk
  • max $1,411/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Oct-31-2018**
" Driving up to the Castle was a surreal experience. It looks like a castle from a story book. The frescoes were everywhere, including the entire room. It made fo..." - Lauren
 
Displaying 1 to 30 of 37 villas