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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Monteriggioni vacation homes

A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

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

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is AED 409
AED 728 total
includes taxes & fees
7 Oct - 8 Oct
Love Nest Siena: 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 AED 34,725
AED 34,746 total
includes taxes & fees
2 Nov - 3 Nov
Ebbio – Villa and Organic Farm in Monteriggioni
A stone building with multiple windows and a chimney.

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 AED 450
AED 511 total
includes taxes & fees
4 Nov - 5 Nov
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 AED 967
AED 1,129 total
includes taxes & fees
6 Oct - 7 Oct
The Arch Among the Hills of Castellina
A two-story house with a stone foundation, wooden shutters, and a covered porch with outdoor furniture.

5. 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
10.0 out of 10, Exceptional, (1 review)
"Pros: Das Haus ist liebevoll eingerichtet, hat zwei schöne Bäder und eine wunderbare schattige Terrasse, von der man ins Grüne schaut, tagsüber ab und zu die Schafe nebenan und abends die Wildschweine hören kann. Das Haus liegt sehr ruhig in einem abgeschiedenen Weiler. Es sind ausreichend Liegestühle vorhanden, um im Garten zu entspannen. Die Klimaanlage im Haus funktioniert bestens. Besonders hervorzuheben sind die sehr herzlichen und hilfsbereiten Vermieter, die auch in dem kleinen Ort wohnen...
Germany
Anonymous traveler
The price is AED 1,620
AED 1,964 total
includes taxes & fees
12 Oct - 13 Oct
Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning
A rustic building with a brick facade, a small arched window, and a door.

6. Cozy Tuscan-style apartment Suitable for families. Pets allowed

Cozy Tuscan-style apartment Suitable 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 AED 620
AED 773 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Tuscan-style apartment Suitable for families. Pets allowed
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and greenery.

7. House with pool for 4 pax

House with pool for 4 pax
Pievescola
9.4 out of 10, Exceptional, (3 reviews)
"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"
Germany
Oliver E.
The price is AED 589
AED 1,139 total
includes taxes & fees
6 Oct - 7 Oct
House with pool for 4 pax
A dining area with a table set for four, a large window with an arched ceiling, and a view of the outdoors.

8. La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
casole d'elsa siena
10.0 out of 10, Exceptional, (43 reviews)
"We stayed in this beautiful clean, fully airconditioned apartment for 12 days, perfect location for trips to the surrounding area like Siena, Florence, Monteriggioni, Volterra & San Gimignano. The apartment is situated in a peaceful Agriturismo with lots of privacy and a great swimming pool. The owners are really hospitable and you feel welcome right away. Highly recommendable."
Netherlands
Linda T.
The price is AED 825
AED 1,358 total
includes taxes & fees
9 Oct - 10 Oct
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
A glass on a wooden table 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 AED 940
AED 1,042 total
includes taxes & fees
6 Oct - 7 Oct
Apartment in Chianti With Pool ID 513
A brick building with a sliding glass door entrance, a large potted plant, and two smaller potted plants outside.

10. GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of
Siena
The price is AED 268
AED 612 total
includes taxes & fees
6 Oct - 7 Oct
GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of
A stone building with a sign reading "VIA DI CALZOLERIA".

11. THE TOLOMEI - apartment in the heart of the main street

THE TOLOMEI - apartment in the heart 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 AED 417
AED 682 total
includes taxes & fees
6 Oct - 7 Oct
THE TOLOMEI - apartment in the heart of the main street
A brick building with a garden, a metal fence, and a clear sky.

12. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is AED 893
AED 1,116 total
includes taxes & fees
11 Oct - 12 Oct
Casa Marisa in Castellina in Chianti
A balcony with potted plants and a view of rolling hills and mountains.

13. A Nest with a View - A Romantic Retreat Within the City Walls

A Nest with a View - A Romantic Retreat Within the City Walls
Radicondoli
The price is AED 590
AED 590 total
includes taxes & fees
1 Nov - 2 Nov
A Nest with a View - A Romantic Retreat Within the City Walls
A rectangular swimming pool with a wooden deck and metal railing, surrounded by a grassy area with trees and a clear sky.

14. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (1 review)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveler
The price is AED 1,287
AED 1,511 total
includes taxes & fees
12 Oct - 13 Oct
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

15. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (13 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 326
AED 379 total
includes taxes & fees
2 Nov - 3 Nov
Casa Vacanze Le Case
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

16. 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, (25 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 AED 334
AED 665 total
includes taxes & fees
6 Oct - 7 Oct
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A bedroom with a bed, a bedside table with a book, a nightstand, and three framed pictures on the wall.

17. 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 517
AED 612 total
includes taxes & fees
5 Nov - 6 Nov
Cozy double room with bathroom in the historic center of San Gimignano.
A building with a stone facade, a door, a window, and a patio area with chairs and a table.

18. Peaceful corner with garden between Chianti and Crete, very close to Old Town

Peaceful corner with garden between Chianti and Crete, very close to Old Town
Casetta
The price is AED 298
AED 405 total
includes taxes & fees
2 Nov - 3 Nov
Peaceful corner with garden between Chianti and Crete, very close to Old Town
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 AED 1,410
AED 1,559 total
includes taxes & fees
7 Oct - 8 Oct
Apartment in Chianti With Pool ID 3939
A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

20. 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
Deluxe Room- A cozy and elegant room in the heart of 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 Monteriggioni Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

8/10 Good
"Although the property and the staff were great, our room was a bit of a disappointment. Junior Sweet was just a giant room with furniture that was uncomfortable to use. In general the room needs an update. Not exactly what we expected. We unfortunately had a neighbor who opened up the gate outside in between our terrace which should have never happen if it had been locked. He did that because he said my husbands iPad was too loud when in fact, his was too loud and my husband who had headphones on could not hear his show so took them off so he could hear it. Needless to say we avoided our terrace after that. Shout out to Chiara and Samantha who took a desert request seriously and made two of my evenings! Michael and David’s were also wonderful!"
Ellen 5-night trip
Posted 16 hours ago
Castiglion del Bosco, A Rosewood Hotel

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