Rolling hills, a winding road, and scattered trees.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Montaione vacation homes

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

1. 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 336
AED 390 total
includes taxes & fees
2 Nov - 3 Nov
Casa Vacanze Le Case
A patio with a table and chairs, an umbrella, and a view of a green fence and plants.

2. 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 890
AED 902 total
includes taxes & fees
1 Nov - 2 Nov
Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi
A stone building with a balcony, arched windows, and potted flowers.

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

"Tenuta Acquabona - Entire Country House" Apartment with Pool
Gambassi Terme
The price is AED 8,751
AED 8,763 total
includes taxes & fees
31 Oct - 1 Nov
"Tenuta Acquabona - Entire Country House" Apartment with Pool
Property grounds

4. 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.

5. 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 940
AED 1,162 total
includes taxes & fees
18 Oct - 19 Oct
Holiday Home 'Cottege' with Shared Pool, Private Terrace and Wi-Fi
A pool with lounge chairs and umbrellas, surrounded by greenery and buildings.

6. 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 1,180
AED 1,201 total
includes taxes & fees
18 Oct - 19 Oct
Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano
A stone building with a central archway, multiple windows, and a paved courtyard with potted plants.

7. Farmhouse 'Le Volpaie - San Benedetto' with Shared Garden and Wi-Fi

Farmhouse 'Le Volpaie - San Benedetto' with Shared Garden and Wi-Fi
San Gimignano
10.0 out of 10, Exceptional, (2 reviews)
"The apartment, although a little rustic, suited most of our needs and the location was beautiful. Our host was very a helpful when we discovered there was no freezer to make ice cubes or freeze our ice pack overnight and she provided ice for us daily as well as freezing the ice pack each night. A wonderful host! A lovely relaxing place to wind down after a busy day touring Tuscany. I recommend this apartment."
Canada
Jacquie B.
Farmhouse 'Le Volpaie - San Benedetto' with Shared Garden and Wi-Fi
A modern bedroom with a large bed, a desk, and three framed pictures on the wall.

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

Cozy double room with bathroom in the historic center of San Gimignano.
San Gimignano City Centre
The price is AED 512
AED 606 total
includes taxes & fees
14 Oct - 15 Oct
Cozy double room with bathroom in the historic center of San Gimignano.
A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

9. Deluxe Room- A cozy and elegant room in the heart of San Gimignano.

Deluxe Room- A cozy and elegant room in the heart of San Gimignano.
San Gimignano City Centre
The price is AED 553
AED 840 total
includes taxes & fees
7 Nov - 8 Nov
Deluxe Room- A cozy and elegant room in the heart of San Gimignano.
A room with a large sliding glass door leading to a pool area with a view of rolling hills and a distant village.

10. Your nest in the Tuscany countryside

Your nest in the Tuscany countryside
Certaldo - Firenze
The price is AED 553
AED 938 total
includes taxes & fees
14 Oct - 15 Oct
Your nest in the Tuscany countryside
A stone building with a hot tub, surrounded by greenery.

11. 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.
Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi
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 1,992
AED 2,278 total
includes taxes & fees
15 Oct - 16 Oct
Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

13. 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 1,136
AED 1,144 total
includes taxes & fees
14 Oct - 15 Oct
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
A pool with lounge chairs and umbrellas, surrounded by greenery and buildings.

14. 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 1,328
AED 1,348 total
includes taxes & fees
18 Oct - 19 Oct
Agriturismo I Borghi – Apartment Tabacco with Pool in San Gimignano
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building with a sloped roof.

15. 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 1,475
AED 1,496 total
includes taxes & fees
18 Oct - 19 Oct
Agriturismo I Borghi – Apartment Zenzero with Pool in San Gimignano
A balcony with a table and chairs overlooking a vineyard.

16. "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 5,163
AED 5,512 total
includes taxes & fees
9 Nov - 10 Nov
"Volpe" Apartment with Pool Reserved for Guests, Wi-Fi, and Air Conditioning
A stone building with a covered outdoor seating area and a brick pathway.

17. 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.
Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi
An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

18. 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 820
AED 1,750 total
includes taxes & fees
14 Oct - 15 Oct
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
A stone building with multiple windows and a chimney.

19. 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 469
AED 532 total
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

20. Agriturismo I Borghi – Apartment Liquirizia with Pool in San Gimignano

Agriturismo I Borghi – Apartment Liquirizia with Pool in San Gimignano
San Gimignano
The price is AED 1,926
AED 1,947 total
includes taxes & fees
13 Nov - 14 Nov
Agriturismo I Borghi – Apartment Liquirizia with Pool in San Gimignano
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 Montaione Hotel Reviews

Castelfalfi

Castelfalfi

10/10 Excellent
"Beautiful place to stay!"
Peter 3-night trip
Posted 3 days ago
Castelfalfi

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