Search Vacation Homes in Siena

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Check prices for these dates

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 HK$800
HK$1,355 total
includes taxes & fees
8 Nov - 9 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 HK$561
HK$1,005 total
includes taxes & fees
11 Nov - 12 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 HK$1,320
HK$1,567 total
includes taxes & fees
8 Nov - 9 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 HK$871
HK$1,408 total
includes taxes & fees
8 Nov - 9 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 HK$73,935
HK$73,979 total
includes taxes & fees
8 Nov - 9 Nov
Ebbio – Villa and Organic Farm in Monteriggioni

6. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is HK$1,904
HK$2,248 total
includes taxes & fees
8 Nov - 9 Nov
The Arch Among the Hills of Castellina

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 HK$1,007
HK$1,143 total
includes taxes & fees
8 Nov - 9 Nov
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 HK$634
HK$801 total
includes taxes & fees
10 Nov - 11 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 HK$1,127
HK$1,267 total
includes taxes & fees
23 Nov - 24 Nov
Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

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)
"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 HK$711
HK$1,336 total
includes taxes & fees
9 Nov - 10 Nov
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

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 HK$686
HK$799 total
includes taxes & fees
8 Nov - 9 Nov
Casa Vacanze Le Case

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 HK$705
HK$1,119 total
includes taxes & fees
7 Nov - 8 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 HK$2,123
HK$2,353 total
includes taxes & fees
7 Nov - 8 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 HK$1,426
HK$1,426 total
includes taxes & fees
20 Nov - 21 Nov
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 HK$440
HK$942 total
includes taxes & fees
7 Nov - 8 Nov
Detached house with a garden, just a few minutes from the Abbey of San Galgano

16. 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 HK$1,100
HK$1,523 total
includes taxes & fees
8 Nov - 9 Nov
Chianti Craft House Badia a Passignano

17. 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 HK$5,668
HK$5,704 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi

18. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is HK$1,901
HK$2,376 total
includes taxes & fees
15 Nov - 16 Nov
Casa Marisa in Castellina in Chianti

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 HK$3,188
HK$3,920 total
includes taxes & fees
8 Nov - 9 Nov
Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

20. Vacation in Poggettone

Vacation in Poggettone
Monteroni d'Arbia
The price is HK$1,267
HK$1,857 total
includes taxes & fees
10 Nov - 11 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.

Learn more about Siena

Medieval brick buildings circle the shell-shaped Piazza del Campo where the thrilling Palio horse race happens twice each summer. Climb the Torre del Mangia for sweeping views, then explore the zebra-striped Duomo where even the marble floor tells fascinating stories.

A historic cathedral with a rainbow, surrounded by traditional buildings.

Explore a world of travel with Expedia