A historic town with terracotta-roof buildings, a prominent church, and a hilltop fortress.

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Our top choices for Siena holiday homes

1. 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 £129
includes taxes & fees
12 Nov - 13 Nov
IL TOLOMEI - new apartment in the middle of the main street

2. 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 £95
includes taxes & fees
12 Nov - 13 Nov
CASA ILARIA - Bright apartment with a view in the historic center

3. 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 £143
includes taxes & fees
15 Nov - 16 Nov
A cozy, Tuscan-style apartment perfect for families. Pets Allowed

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

Siena Love Nest: Romantic Suite with Spa & Jacuzzi
Toscana
The price is £142
includes taxes & fees
12 Nov - 13 Nov
Siena Love Nest: Romantic Suite with Spa & Jacuzzi

5. Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is £7,018
includes taxes & fees
15 Nov - 16 Nov
Ebbio – Villa and Organic Farm in Monteriggioni

6. 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 £108
includes taxes & fees
12 Nov - 13 Nov
Agriturismo La Ferrozzola

7. A peaceful spot with a garden between Chianti and Crete, near the old town

A peaceful spot with a garden between Chianti and Crete, near the old town
Casetta
The price is £78
includes taxes & fees
12 Nov - 13 Nov
A peaceful spot with a garden between Chianti and Crete, near the old town

8. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included
Monteroni d'Arbia
The price is £95
includes taxes & fees
23 Nov - 24 Nov
Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

9. 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 £130
includes taxes & fees
16 Nov - 17 Nov
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

10. 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 £76
includes taxes & fees
14 Nov - 15 Nov
Casa Vacanze Le Case

11. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is £107
includes taxes & fees
12 Nov - 13 Nov
Exclusive Stone Tower.

12. 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 £135
includes taxes & fees
12 Nov - 13 Nov
A Nest with a View - A Romantic Getaway Within the City Walls

13. Apartment in Chianti With Pool ID 513

Apartment in Chianti With Pool ID 513
Casole d'Elsa
The price is £223
includes taxes & fees
16 Nov - 17 Nov
Apartment in Chianti With Pool ID 513

14. Detached house with a garden, just a few minutes from the Abbey of San Galgano

Detached house with a garden, just a few minutes from the Abbey of San Galgano
Toscana
10.0 out of 10, Exceptional, (1 review)
"Petite maison cosy et juste parfaite pour deux personnes. La localisation est très bonne, à l’entrée du village de Monticiano. L’accueil a été enthousiaste et la communication très fluide. Merci pour ce beau séjour ! On recommande !"
United States
Julie M.
The price is £97
includes taxes & fees
13 Nov - 14 Nov
Detached house with a garden, just a few minutes from the Abbey of San Galgano

15. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (13 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is £148
includes taxes & fees
12 Nov - 13 Nov
Chianti Craft House Badia a Passignano

16. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is £226
includes taxes & fees
15 Nov - 16 Nov
Casa Marisa in Castellina in Chianti

17. Vacation in Poggettone

Vacation in Poggettone
Monteroni d'Arbia
The price is £173
includes taxes & fees
23 Nov - 24 Nov
Vacation in Poggettone

18. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi
Poggiobrucoli
The price is £211
includes taxes & fees
24 Nov - 25 Nov
Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

19. 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 traveller
The price is £372
includes taxes & fees
16 Nov - 17 Nov
Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

20. 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 £120
includes taxes & fees
12 Nov - 13 Nov
Comfortable double room with a bathroom in the historic center 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 Siena Hotel Reviews

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Siena Holiday Homes information

Number of reviews
75
Accommodation
109 Holiday Homes
Lowest Price
£76
Highest Price
£7,018