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

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 ￥14,521
￥16,857 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥38,422
￥38,953 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥378,641
￥379,173 total
includes taxes & fees
Oct 31 - Nov 1
"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 ￥40,620
￥50,178 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥50,974
￥51,859 total
includes taxes & fees
Oct 18 - Oct 19
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 price is ￥46,624
￥47,509 total
includes taxes & fees
Oct 14 - Oct 15
Farmhouse 'Le Volpaie - San Benedetto' with Shared Garden and Wi-Fi
A bedroom with a bed, a bedside table with a book, a nightstand, 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 ￥22,124
￥26,195 total
includes taxes & fees
Oct 14 - Oct 15
Cozy double room with bathroom in the historic center 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.

9. Your nest in the Tuscany countryside

Your nest in the Tuscany countryside
Certaldo - Firenze
The price is ￥23,894
￥40,531 total
includes taxes & fees
Oct 14 - Oct 15
Your nest in the Tuscany countryside
A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

10. 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 ￥23,894
￥36,284 total
includes taxes & fees
Oct 14 - Oct 15
Deluxe Room- A cozy and elegant room in the heart of San Gimignano.
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.
The price is ￥110,285
￥111,172 total
includes taxes & fees
Oct 28 - Oct 29
Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

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

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
The price is ￥49,063
￥49,417 total
includes taxes & fees
Oct 14 - Oct 15
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
A swimming pool with a hot tub, outdoor seating, and a view of a hillside house.

13. 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 ￥86,019
￥98,409 total
includes taxes & fees
Oct 15 - Oct 16
Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden
An aerial view of a property with a swimming pool, a large house, and surrounding gardens.

14. 'La Ripa - Apartment Il Fienile' with Shared Pool & Wi-Fi

'La Ripa - Apartment Il Fienile' with Shared Pool & Wi-Fi
San Gimignano
The price is ￥85,124
￥85,656 total
includes taxes & fees
Oct 14 - Oct 15
'La Ripa - Apartment Il Fienile' with Shared Pool & Wi-Fi
A pool with lounge chairs and umbrellas, surrounded by greenery and buildings.

15. 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 ￥57,451
￥58,338 total
includes taxes & fees
Oct 18 - Oct 19
Agriturismo I Borghi – Apartment Tabacco with Pool in San Gimignano
An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

16. 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 ￥35,399
￥75,577 total
includes taxes & fees
Oct 14 - Oct 15
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
A rectangular swimming pool with a stone border, surrounded by lounge chairs and umbrellas, set against a stone building with a tiled roof, amidst a grassy area with trees.

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 ￥20,253
￥22,986 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
A dining area with a table set for two, a view of a vineyard, and a wooden table with a small decorative item.

18. Villa Latini Agriturismo La Capanna

Villa Latini Agriturismo La Capanna
Montespertoli
Villa Latini Agriturismo La Capanna
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building with a sloped roof.

19. 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 ￥63,835
￥64,722 total
includes taxes & fees
Oct 18 - Oct 19
Agriturismo I Borghi – Apartment Zenzero with Pool in San Gimignano
A view through a wooden door of a courtyard with stone walls and potted plants.

20. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is ￥22,124
￥32,036 total
includes taxes & fees
Oct 18 - Oct 19
Chianti Craft House Badia a Passignano
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

Castelfalfi

Castelfalfi

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

Find out more about Montaione

Montaione Vacation Homes information

Number of reviews
40
Accommodation
101 Vacation Homes
Lowest Price
￥16,857
Highest Price
￥379,173