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Our top choices for Montemassi vacation homes
Private House with Exclusive Swimming Pool Heated and Amazing View
Private House with Exclusive Swimming Pool Heated and Amazing ViewBoccheggiano
9.6 out of 10, Exceptional, (56)
"Everything was great. The pool was warm. Views are fantastic stretching out to the sea. The town has a good supermarket. Only went to one restaurant, Dell'Upo, but it was good so went back most nights. The hosts were helpful and informative. Planning a return."
Patrick H.
The price is AED 12,472
AED 14,812 total
includes taxes & fees
31 Dec - 1 January 2026
Four-room apartment with 3 double bedrooms and 2 bathrooms
Four-room apartment with 3 double bedrooms and 2 bathroomsGrosseto
10.0 out of 10, Exceptional, (1)
The price is AED 538
AED 729 total
includes taxes & fees
29 Dec - 30 Dec
La Fonte di Vivalda
La Fonte di VivaldaSuvereto
7.0 out of 10, Good, (2)
"tutto molto bello"
Andrea
Comfort, relaxation and nature
Comfort, relaxation and natureMonticiano
10.0 out of 10, Exceptional, (1)
"Appartamento perfetto non manca nulla e proprietari accoglienti, e gentilissimi. Da tornare"
Sandra V.
The price is AED 310
AED 439 total
includes taxes & fees
22 Dec - 23 Dec
Two-room apartment in residence with swimming pool and restaurant
Two-room apartment in residence with swimming pool and restaurantGrosseto
8.0 out of 10, Very Good, (1)
"Tutto ok"
PAOLO T.
The price is AED 263
AED 367 total
includes taxes & fees
22 Dec - 23 Dec
The price is AED 516
AED 594 total
includes taxes & fees
22 Dec - 23 Dec
Exclusive Stone Tower.
Exclusive Stone Tower.Casciano
9.8 out of 10, Exceptional, (7)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
Michael G.
The price is AED 364
AED 622 total
includes taxes & fees
4 Jan - 5 January 2026
Detached house with garden a few minutes from the abbey of San Galgano
Detached house with garden a few minutes from the abbey of San GalganoToscana
The price is AED 215
AED 520 total
includes taxes & fees
22 Dec - 23 Dec
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.
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Top Montemassi Hotel Reviews
Rosewood Castiglion del Bosco
10/10 Excellent
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