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 38 villas
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 5 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $157 when you book by Feb-20-2019**
" 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 $133 Photo of Tuscan Apartment in Historic Castle
  • min $817/wk
  • max $1,326/wk
  • min $735/wk
  • max $1,193/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $133 when you book by Feb-20-2019**
" 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 $249 Photo of Tuscan Apartment in Historic Castle
  • min $1,385/wk
  • max $2,487/wk
  • min $1,247/wk
  • max $2,238/wk
  • Min Stay: 3 days
Sleeps 6 people
  • 3 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $249 when you book by Feb-20-2019**
" Overall our stay at the villa was a wonderful experience and the views amazing. Just wish we could have stayed around long enough to enjoy more!..." - Anne
Save $103 Photo of Tuscan Apartment in Historic Castle
  • min $516/wk
  • max $1,029/wk
  • min $464/wk
  • max $926/wk
  • Min Stay: 3 days
Sleeps 2 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $103 when you book by Feb-20-2019**
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $735/wk
  • max $1,617/wk
  • min $662/wk
  • max $1,455/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 single bedrooms
  • 1 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $162 when you book by Feb-20-2019**
" 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 $157 Photo of Tuscan Apartment in Historic Castle
  • min $978/wk
  • max $1,568/wk
  • min $880/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 Feb-20-2019**
" 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
Save $138 Photo of CastleApartment Rental in Tuscany, Montespertoli (Chianti Area)
  • min $899/wk
  • max $1,381/wk
  • min $809/wk
  • max $1,243/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $138 when you book by Feb-20-2019**
Save $135 Photo of Tuscan Apartment in Historic Castle
  • min $793/wk
  • max $1,350/wk
  • min $714/wk
  • max $1,215/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $135 when you book by Feb-20-2019**
Save $155 Photo of Tuscan Apartment in Historic Castle
  • min $735/wk
  • max $1,545/wk
  • min $662/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 Feb-20-2019**
Save $125 Photo of Tuscan Apartment in Historic Castle
  • min $663/wk
  • max $1,252/wk
  • min $597/wk
  • max $1,127/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Independent House
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $125 when you book by Feb-20-2019**
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 Feb-20-2019**
" 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 $213 Photo of Tuscan Apartment in Historic Castle
  • min $1,104/wk
  • max $2,133/wk
  • min $994/wk
  • max $1,920/wk
  • Min Stay: 3 days
Sleeps 8 people
  • 4 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $213 when you book by Feb-20-2019**
" We loved it. We were 6 woman so we bought local fare and cooked in our big kitchen. ..." - Alice Celine
Save $174 Photo of Tuscan Apartment in Historic Castle
  • min $1,066/wk
  • max $1,738/wk
  • min $959/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 Feb-20-2019**
Save $118 Photo of Tuscan Apartment in Historic Castle
  • min $559/wk
  • max $1,176/wk
  • min $503/wk
  • max $1,058/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $118 when you book by Feb-20-2019**
" Love this property. Second year in a row I have been there...." - Sadia
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $735/wk
  • max $1,617/wk
  • min $662/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 Feb-20-2019**
" 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 $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 Feb-20-2019**
Save $179 Photo of Tuscan Apartment in Historic Castle
  • min $916/wk
  • max $1,790/wk
  • min $824/wk
  • max $1,611/wk
  • Min Stay: 3 days
Sleeps 4 to 6 people
  • 3 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $179 when you book by Feb-20-2019**
" Very good. However, it was 104 most days and didn't cool off much at night. Good home base for day trips...." - Kelly
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 Feb-20-2019**
Save $167 Photo of Tuscan Apartment in Historic Castle
  • min $748/wk
  • max $1,668/wk
  • min $673/wk
  • max $1,501/wk
  • Min Stay: 3 days
Sleeps 2 to 4 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $167 when you book by Feb-20-2019**
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $810/wk
  • max $1,617/wk
  • min $729/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 Feb-20-2019**
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $882/wk
  • max $1,617/wk
  • min $794/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 Feb-20-2019**
" Beautiful, large castle in a picture perfect location that seemed like something out of a Tuscan fantasy. ..." - Deborah
Save $119 Photo of Tuscan Apartment in Historic Castle
  • min $727/wk
  • max $1,192/wk
  • min $654/wk
  • max $1,073/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $119 when you book by Feb-20-2019**
" Ambiance. Staff was very good...." - Will
Save $168 Photo of Tuscan Apartment in Historic Castle
  • min $735/wk
  • max $1,676/wk
  • min $662/wk
  • max $1,508/wk
  • Min Stay: 3 days
Sleeps 4 people
  • 2 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $168 when you book by Feb-20-2019**
" 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 $191 Photo of Tuscan Apartment in Historic Castle
  • min $882/wk
  • max $1,911/wk
  • min $794/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 Feb-20-2019**
" It was comfortable, clean, and conveniently located. ..." - Misty
Save $162 Photo of Tuscan Apartment in Historic Castle
  • min $735/wk
  • max $1,617/wk
  • min $662/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
** Save up to $162 when you book by Feb-20-2019**
" 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 $412 Photo of Tuscan Apartment in Historic Castle
  • min $2,058/wk
  • max $4,116/wk
  • min $1,852/wk
  • max $3,704/wk
  • Min Stay: 3 days
Sleeps 8 to 9 people
  • 4 double bedrooms
  • 3 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $412 when you book by Feb-20-2019**
" We had a very pleasant stay and would recommend the property...." - Amy
Save $226 Photo of Tuscan Apartment in Historic Castle
  • min $1,206/wk
  • max $2,261/wk
  • min $1,085/wk
  • max $2,035/wk
  • Min Stay: 3 days
Sleeps 4 to 5 people
  • 2 double bedrooms
  • 2 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $226 when you book by Feb-20-2019**
" Good...." - Randee
Save $127 Photo of Tuscan Apartment in Historic Castle
  • min $647/wk
  • max $1,265/wk
  • min $582/wk
  • max $1,139/wk
  • Min Stay: 3 days
Sleeps 2 to 3 people
  • 1 double bedrooms
  • 1 bathrooms
  • Swimming Pool
  • Washing Machine
  • Maid Service
** Save up to $127 when you book by Feb-20-2019**
" The castle is beautiful...." - Serena
Save $176 Photo of Tuscan Apartment in Historic Castle
  • min $810/wk
  • max $1,764/wk
  • min $729/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 Feb-20-2019**
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 Feb-20-2019**
 
Displaying 1 to 30 of 38 villas