Rolling hills, a winding road, and scattered trees.

Search Vacation Homes in Montaione

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Montaione vacation homes

A patio with a table and chairs, an umbrella, and a view of a green fence and plants.

1. Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi

Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi
Certaldo
10.0 out of 10, Exceptional, (1 review)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
Germany
Anonymous traveler
The price is AED 878
AED 891 total
includes taxes & fees
31 Oct - 1 Nov
Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

2. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is AED 338
AED 392 total
includes taxes & fees
2 Nov - 3 Nov
Casa Vacanze Le Case
A modern kitchen with white cabinets, a microwave, and a dining area with a round table and chairs.

3. New Listing

New Listing
Dogana
The price is AED 371
AED 453 total
includes taxes & fees
25 Oct - 26 Oct
New Listing
A stone building with a balcony, arched windows, and potted flowers.

4. "Tenuta Acquabona - Entire Country House" Apartment with Pool

"Tenuta Acquabona - Entire Country House" Apartment with Pool
Gambassi Terme
The price is AED 7,927
AED 7,939 total
includes taxes & fees
31 Oct - 1 Nov
"Tenuta Acquabona - Entire Country House" Apartment with Pool
Outdoor dining

5. Villa Sunshine - traditional tuscan home

Villa Sunshine - traditional tuscan home
Gambassi Terme
Villa Sunshine - traditional tuscan home
A large house with a tennis court, surrounded by hills and trees.

6. Holiday Home 'Cottege' with Shared Pool, Private Terrace and Wi-Fi

Holiday Home 'Cottege' with Shared Pool, Private Terrace and Wi-Fi
Palaia
The price is AED 946
AED 1,168 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Home 'Cottege' with Shared Pool, Private Terrace and Wi-Fi
A pool with lounge chairs and umbrellas, surrounded by greenery and buildings.

7. Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano

Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano
San Gimignano
The price is AED 1,187
AED 1,207 total
includes taxes & fees
25 Oct - 26 Oct
Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano
A bedroom with a bed, a bedside table with a book, a nightstand, and three framed pictures on the wall.

8. Comfortable double room with a bathroom in the historic center of San Gimignano.

Comfortable double room with a bathroom in the historic center of San Gimignano.
San Gimignano City Centre
The price is AED 515
AED 610 total
includes taxes & fees
24 Oct - 25 Oct
Comfortable double room with a bathroom in the historic center of San Gimignano.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

9. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
The price is AED 1,269
AED 1,277 total
includes taxes & fees
17 Nov - 18 Nov
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
A stone building with a hot tub, surrounded by greenery.

10. Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi

Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi
San Gimignano
10.0 out of 10, Exceptional, (2 reviews)
"It was spacious and clean. Nice kitchen though we did not cook. Coffee maker took some getting used to. Showers on the small side but worked well. Lovely property. Enjoyed our time here. "
United States
Dale M.
The price is AED 2,307
AED 2,327 total
includes taxes & fees
28 Oct - 29 Oct
Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi
A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

11. Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.

Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.
San Gimignano City Centre
The price is AED 556
AED 845 total
includes taxes & fees
25 Oct - 26 Oct
Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.
A swimming pool with a hot tub, outdoor seating, and a view of a hillside house.

12. Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden

Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden
San Gimignano
9.2 out of 10, Wonderful, (13 reviews)
"Great place in the Tuscany area. The views are spectacular, the property is just like the pictures. Would definitely stay here again"
United States
Valerie S.
The price is AED 2,390
AED 2,679 total
includes taxes & fees
10 Nov - 11 Nov
Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden
An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

13. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"
United States
Susan A.
The price is AED 495
AED 1,376 total
includes taxes & fees
21 Nov - 22 Nov
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
A stone building with a covered outdoor seating area and a brick pathway.

14. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi
San Gimignano
10.0 out of 10, Exceptional, (1 review)
"We stayed for a week at La Ripa. It is a very beautiful and quiet place. It is a few minutes from San Gimignano and it is a central place to visit nice villages in Toscany. Rodrigo was there to welcome us and securing for us an optimal stay. He was amicable and available. This is a place we are highly recommending."
Canada
Anne-Marie M.
The price is AED 2,359
AED 2,371 total
includes taxes & fees
25 Oct - 26 Oct
Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi
A modern hotel room with a walk-in closet, a vanity with a mirror, and a red accent wall.

15. A beautiful, elegant, and sophisticated superior room in the heart of San Gimignano.

A beautiful, elegant, and sophisticated superior room in the heart of San Gimignano.
San Gimignano City Centre
The price is AED 598
AED 894 total
includes taxes & fees
24 Oct - 25 Oct
A beautiful, elegant, and sophisticated superior room in the heart of San Gimignano.
A pool with lounge chairs and umbrellas, surrounded by greenery and buildings.

16. Agriturismo I Borghi – Apartment Tabacco with Pool in San Gimignano

Agriturismo I Borghi – Apartment Tabacco with Pool in San Gimignano
San Gimignano
The price is AED 1,336
AED 1,357 total
includes taxes & fees
25 Oct - 26 Oct
Agriturismo I Borghi – Apartment Tabacco with Pool in San Gimignano
A stone building with multiple windows and a chimney.

17. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is AED 472
AED 535 total
includes taxes & fees
10 Nov - 11 Nov
Agriturismo La Ferrozzola
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building with a sloped roof.

18. Agriturismo I Borghi – Apartment Zenzero with Pool in San Gimignano

Agriturismo I Borghi – Apartment Zenzero with Pool in San Gimignano
San Gimignano
The price is AED 1,485
AED 1,505 total
includes taxes & fees
25 Oct - 26 Oct
Agriturismo I Borghi – Apartment Zenzero with Pool in San Gimignano
A balcony with a table and chairs overlooking a vineyard.

19. "Volpe" Apartment with Pool Reserved for Guests, Wi-Fi, and Air Conditioning

"Volpe" Apartment with Pool Reserved for Guests, Wi-Fi, and Air Conditioning
San Gimignano
10.0 out of 10, Exceptional, (2 reviews)
"Un séjour très agréable dans cette maison et un merci chaleureux à Roberto pour son accueil parfait."
United States
Bruno G.
The price is AED 1,854
AED 2,205 total
includes taxes & fees
25 Oct - 26 Oct
"Volpe" Apartment with Pool Reserved for Guests, Wi-Fi, and Air Conditioning
A dining area with a table set for two, a view of a vineyard, and a wooden table with a small decorative item.

20. Villa Latini Agriturismo La Capanna

Villa Latini Agriturismo La Capanna
Montespertoli
Villa Latini Agriturismo La Capanna
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montaione Hotel Reviews

Boccioleto Resort&Spa

Boccioleto Resort&Spa

8/10 Good
"Beautiful property in Tuscany with a lovely pool and complimentary breakfast."
Josie 5-night trip
Posted 7 days ago
Boccioleto Resort&Spa

Explore a world of travel with Expedia