A cobblestone square with historic buildings, a fountain, and a church with a bell tower.

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Monteriggioni vacation homes

A bedroom with a bed, a vanity with a mirror, and LED strip lighting.

1. Siena Love Nest: Romantic Suite with Spa & Jacuzzi

Siena Love Nest: Romantic Suite with Spa & Jacuzzi
Toscana
The price is ￥17,397
￥30,928 total
includes taxes & fees
Oct 27 - Oct 28
Siena Love Nest: Romantic Suite with Spa & Jacuzzi
A rustic villa with a garden, a pond, and a mountainous backdrop.

2. Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is ￥1,476,093
￥1,476,972 total
includes taxes & fees
Oct 28 - Oct 29
Ebbio – Villa and Organic Farm in Monteriggioni
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

3. 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 ￥19,907
￥22,601 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
A stone building with a gravel path, outdoor seating, and greenery.

4. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is ￥37,957
￥44,810 total
includes taxes & fees
Nov 2 - Nov 3
The Arch Among the Hills of Castellina
A horse grazing under a tree in a grassy area with a small building in the background.

5. A cozy, Tuscan-style apartment perfect for families. Pets Allowed

A cozy, Tuscan-style apartment perfect for families. Pets Allowed
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."
United States
Shanti R.
The price is ￥26,359
￥32,861 total
includes taxes & fees
Oct 27 - Oct 28
A cozy, Tuscan-style apartment perfect for families. Pets Allowed
A two-story house with a stone foundation, wooden shutters, and a covered porch with outdoor furniture.

6. Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning
Casole d'Elsa
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Das Haus ist gut ausgestattet und liegt schön ruhig. Abends kann man das Zirpen der Grillen genießen, den Kauz hören und es kam auch ein Dachs vorbei! Wunderbar für Naturliebhaber. Es ist abseits gelegen. Die Gastgeber sind ausgesprochen nett und haben viele Tipps ! Sehr nette Gastfreundschaft. Ein Ort zum entspannen in der Toscana."
Germany
Anonymous traveler
The price is ￥63,648
￥78,265 total
includes taxes & fees
Nov 2 - Nov 3
Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning
A brick building with a garden, a metal fence, and a clear sky.

7. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is ￥37,957
￥47,446 total
includes taxes & fees
Oct 28 - Oct 29
Casa Marisa in Castellina in Chianti
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and greenery.

8. House with pool for 4 pax

House with pool for 4 pax
Pievescola
9.4 out of 10, Exceptional, (3 reviews)
"Peaceful, tranquil & quiet retreat with gorgeous but unheated pool - so very refreshing! Lovely, airy & cool rooms. Twin beds were hard but double bed was comfortable. Check side of recycling bin by gate to know what items can be recycled - written instructions were confusing. Hostess Lea delightful & welcoming with hostess Camilla very helpful & warmly wishing us the best!"
Canada
Judith C.
The price is ￥25,041
￥48,939 total
includes taxes & fees
Oct 27 - Oct 28
House with pool for 4 pax
A glass on a wooden surface with a pool and a building in the background.

9. Apartment in Chianti With Pool ID 513

Apartment in Chianti With Pool ID 513
Casole d'Elsa
The price is ￥42,395
￥46,985 total
includes taxes & fees
Oct 27 - Oct 28
Apartment in Chianti With Pool ID 513
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

10. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is ￥14,190
￥27,897 total
includes taxes & fees
Oct 27 - Oct 28
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

11. 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 ￥13,697
￥15,946 total
includes taxes & fees
Nov 2 - Nov 3
Casa Vacanze Le Case
A large, dark wooden door with a glass panel above it, set within a brick wall.

12. IL TOLOMEI - new apartment in the middle of the main street

IL TOLOMEI - new apartment in the middle of the main street
Siena City Centre
8.4 out of 10, Very good, (5 reviews)
"I stayed for a month and found the apartment ti be very comfortable and si convenient for all that Siena has to offer."
United States
Louise B.
The price is ￥15,975
￥27,062 total
includes taxes & fees
Oct 27 - Oct 28
IL TOLOMEI - new apartment in the middle of the main street
A bedroom with a bed, a bedside table with a book, a nightstand, and three framed pictures on the wall.

13. 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 ￥21,966
￥26,008 total
includes taxes & fees
Oct 27 - Oct 28
Comfortable double room with a bathroom in the historic center of San Gimignano.
A room with a large window, a view of a balcony with outdoor furniture, and a kitchen area with a sink.

14. CASA ILARIA - Bright apartment with a view in the historic center

CASA ILARIA - Bright apartment with a view in the historic center
Siena City Centre
8.0 out of 10, Very good, (5 reviews)
"Location was close to restaurants and bars. View from the windows is spectacular. Lots of ups and downs for walking but typical of Italy. Would have liked to see a toaster and handrail on stairs to bedroom, otherwise well equipped. An information booklet including operation of appliances would be helpful."
United States
Phil S.
The price is ￥11,183
￥20,033 total
includes taxes & fees
Oct 27 - Oct 28
CASA ILARIA - Bright apartment with a view in the historic center
A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

15. 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 ￥23,723
￥36,024 total
includes taxes & fees
Oct 28 - Oct 29
Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.
A narrow alleyway with a stone archway leading to a building with a brick facade.

16. A Nest with a View - A Romantic Getaway Within the City Walls

A Nest with a View - A Romantic Getaway Within the City Walls
Radicondoli
The price is ￥27,281
￥27,281 total
includes taxes & fees
Nov 1 - Nov 2
A Nest with a View - A Romantic Getaway Within the City Walls
A view through a wooden door of a courtyard with stone walls and potted plants.

17. 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 ￥21,966
￥31,807 total
includes taxes & fees
Oct 28 - Oct 29
Chianti Craft House Badia a Passignano
A rural property with a stone building, a dirt path leading to it, and surrounding olive trees.

18. Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi

Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi
Castelnuovo Berardenga
8.0 out of 10, Very good, (1 review)
"Pros: Posto meraviglioso. Bellissima location e bellissimo panorama Cons: Un po' più di cura e pulizia nella zona piscina. Jacuzzi chiusa e pensavamo di trovarla aperta"
Italy
Anonymous traveler
The price is ￥113,167
￥113,870 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

19. Apartment in Chianti With Pool ID 3939

Apartment in Chianti With Pool ID 3939
Casole d'Elsa
The price is ￥62,475
￥69,074 total
includes taxes & fees
Oct 27 - Oct 28
Apartment in Chianti With Pool ID 3939
An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

20. 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 ￥21,087
￥59,219 total
includes taxes & fees
Nov 15 - Nov 16
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
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 Monteriggioni Hotel Reviews

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Beautiful property, staff was always helpful. Food was excellent."
Anita 5-night trip
Posted 5 hours ago
La Certosa di Pontignano

Find out more about Monteriggioni

Monteriggioni Vacation Homes information

Number of reviews
68
Accommodation
1532 Vacation Homes
Lowest Price
￥15,946
Highest Price
￥1,476,972