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

Holiday Homes in Siena

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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 NZ$310
includes taxes & fees
11 Nov - 12 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 NZ$229
includes taxes & fees
11 Nov - 12 Nov
CASA ILARIA - Bright apartment with a view in the historic center

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

Siena Love Nest: Romantic Suite with Spa & Jacuzzi
Toscana
The price is NZ$329
includes taxes & fees
22 Nov - 23 Nov
Siena Love Nest: Romantic Suite with Spa & Jacuzzi

4. 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 NZ$339
includes taxes & fees
17 Nov - 18 Nov
A cozy, Tuscan-style apartment perfect for families. Pets Allowed

5. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The Arch Among the Hills of Castellina

6. Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is NZ$16,742
includes taxes & fees
15 Nov - 16 Nov
Ebbio – Villa and Organic Farm in Monteriggioni

7. 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 NZ$259
includes taxes & fees
30 Nov - 1 Dec
Agriturismo La Ferrozzola

8. 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 NZ$181
includes taxes & fees
22 Nov - 23 Nov
A peaceful spot with a garden between Chianti and Crete, near the old town

9. 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 NZ$221
includes taxes & fees
23 Nov - 24 Nov
Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

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 NZ$170
includes taxes & fees
13 Nov - 14 Nov
Casa Vacanze Le Case

11. 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)
"Unable to sleep! Do not stay here during the summer. Even though it seemed to cool off at night, and even with a fan, it was so hot in the top bedroom that we sweat all night and did not sleep a wink. Also, there was a dog barking next door so that made it even harder to sleep. For some reason, there isn’t a pool listed in the description but when we complained about the heat, we were told we could use the pool. The property is beautiful but unbearable in terms of getting sleep, I do not...
United States
Michael F.
The price is NZ$302
includes taxes & fees
13 Nov - 14 Nov
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

12. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is NZ$268
includes taxes & fees
11 Nov - 12 Nov
Exclusive Stone Tower.

13. Apartment in Chianti With Pool ID 513

Apartment in Chianti With Pool ID 513
Casole d'Elsa
The price is NZ$533
includes taxes & fees
18 Nov - 19 Nov
Apartment in Chianti With Pool ID 513

14. 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 NZ$325
includes taxes & fees
10 Dec - 11 Dec
A Nest with a View - A Romantic Getaway Within the City Walls

15. 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 NZ$227
includes taxes & fees
10 Dec - 11 Dec
Detached house with a garden, just a few minutes from the Abbey of San Galgano

16. 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 traveller
The price is NZ$1,267
includes taxes & fees
8 Dec - 9 Dec
Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi

17. 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 NZ$996
includes taxes & fees
10 Dec - 11 Dec
Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

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 NZ$504
includes taxes & fees
24 Nov - 25 Nov
Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

19. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is NZ$538
includes taxes & fees
15 Nov - 16 Nov
Casa Marisa in Castellina in Chianti

20. Vacation in Poggettone

Vacation in Poggettone
Monteroni d'Arbia
The price is NZ$410
includes taxes & fees
23 Nov - 24 Nov
Vacation in Poggettone
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

Find out more about Siena

Siena Holiday Homes information

Number of reviews
63
Accommodation
119 Holiday Homes
Lowest Price
NZ$170
Highest Price
NZ$16,742

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