Photo by Paula Warren

Find Hotels with a Pool in Montespertoli

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Montespertoli Hotels with a Pool

Next weekend
In two weeks

Top Montespertoli Hotels with a Pool

Tenuta Moriano

Montespertoli
10.0 out of 10, Exceptional, (6)
"We stayed as a family and enjoyed the properties facilities including pool swings and outdoor games. The Tuscan dinner was enjoyable with amazing views. Property in convenient to local restaurants and provided a great recommendation list. We thoroughly enjoyed our stay and would return. Great value. My only suggestion would be to provide some basics on arrival such as tea, coffee, milk. A hairdryer would also be useful."
Australia
Amy
The price is SAR 201
SAR 523 total
includes taxes & fees
11 Dec - 12 Dec
Tenuta Moriano

Podere dell'Anselmo

Montespertoli
9.6 out of 10, Exceptional, (31)
"Excellent stay, would highly recommend "
United States
Santina
The price is SAR 479
SAR 544 total
includes taxes & fees
18 Dec - 19 Dec
Podere dell'Anselmo

Romantic apartment in Chianti with pool and vineyard views

Toscana
The price is SAR 481
SAR 817 total
includes taxes & fees
8 Dec - 9 Dec
Romantic apartment in Chianti with pool and vineyard views

Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Montespertoli
10.0 out of 10, Exceptional, (1)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is SAR 6,686
SAR 6,695 total
includes taxes & fees
8 Dec - 9 Dec
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Montespertoli
10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
United States
Ed M.
The price is SAR 5,681
SAR 6,507 total
includes taxes & fees
7 Jan - 8 January 2026
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Montespertoli
10.0 out of 10, Exceptional, (12)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
The price is SAR 5,462
SAR 6,240 total
includes taxes & fees
9 Dec - 10 Dec
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country

Montespertoli
10.0 out of 10, Exceptional, (22)
"We stayed for 4 nights with our 2 sons using this as a base to explore Tuscany including Florence, Sienna, and Pisa. It was a perfect location arriving back each evening to enjoy the pool and relax on the beautiful Tuscan countryside. Nicola was an excellent host and was there to answer any questions, make excellent recommendations and provide any services we needed. "
United States
John P.
The price is SAR 1,136
SAR 1,298 total
includes taxes & fees
7 Jan - 8 January 2026
Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country

Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef

Poppiano
8.0 out of 10, Very Good, (3)
"Tuscany really is as lovely as we dreamed. We found the property communication to be excellent and registration very informative. The recommendations for sights and restaurants were absolutely spot on. We were two couples and the space does work well for two couples. One bedroom had an ensuite and the second bedroom had a bathroom adjacent. The kitchen is small but functional for 2. We would suggest that the property description be updated as it is a little misleading. The kitchen supplies are...
Canada
Dinah H.
The price is SAR 1,508
SAR 1,713 total
includes taxes & fees
8 Dec - 9 Dec
Cozy apartment for 4/5 pax in a cottage in Chianti,Wifi,Swimmingpool,AIR-CO,Chef

Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi

Montespertoli
10.0 out of 10, Exceptional, (2)
"We had the best time. The view is spectacular. The rooms are spacious very secure property. The property was clean and well appointed. We had a special request during our stay of a chef to cook us a real Italian meal. Our host Elena took the challenge on herself with the help of her family. The meal she cooked was the highlight of our entire vacation. She was a great host to deal with and we’d love to go back there again."
United States
Charlie B.
The price is SAR 3,496
SAR 3,505 total
includes taxes & fees
20 Dec - 21 Dec
Apartment 'La Terrazza' with Shared Pool, Private Terrace & Wi-Fi

Charming apartment in the heart of Tuscany

Montespertoli
The price is SAR 874
SAR 979 total
includes taxes & fees
20 Dec - 21 Dec
Charming apartment in the heart of Tuscany
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Montespertoli Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

What's it like visiting Montespertoli?
If lounging next to a pool is your idea of the perfect getaway, you may want to check out relaxing Montespertoli, which offers 37 places to stay with pools. During your trip, you can explore sights such as Montegufoni Castle and Piazza Machiavelli, and then relax and unwind poolside at one of the accommodations in Montespertoli that guests like for their pools.
What are some hotels with pools in Montespertoli?
Villa Le Calvane: Features 3 outdoor pools, a children's pool, and a full-service spa. Tenuta Moriano: Offers a children's pool, a seasonal outdoor pool, and spa services. Le Mandrie di Ripalta: Provides free self parking, a seasonal outdoor pool, and complimentary bicycles. Tuscan Refuge with Private Pool: Features complimentary wireless internet access, a pool, and kitchens. Montegufoni 23 - Apartment with swimming pool: Offers complimentary wireless internet access, a communal pool, and kitchens.
How many hotels with pools are there in Montespertoli?
Expedia's 37 hotels in Montespertoli give you a great choice for your poolside getaway.
What is there to see and do in Montespertoli?
Make a point to visit attractions like Il Fiaschetto. Discover sights such as Montegufoni Castle, Piazza Machiavelli, and Castello Sonnino during your stay. The countryside and biking are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Montespertoli?
You may want to consider a place to stay that has an outdoor pool if you plan to visit Montespertoli in the warmest months of August, July, or June when the average temperature is 73°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 44°F.