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

Siena Vacation Rentals

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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 Siena vacation homes

A large, dark wooden door with a glass panel above it, set within a brick wall.

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 CA $142
CA $240 total
includes taxes & fees
Nov 3 - Nov 4
IL TOLOMEI - new apartment in the middle of the main street
A room with a large window, a view of a balcony with outdoor furniture, and a kitchen area with a sink.

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 CA $99
CA $178 total
includes taxes & fees
Nov 5 - Nov 6
CASA ILARIA - Bright apartment with a view in the historic center
A horse grazing under a tree in a grassy area with a small building in the background.

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 CA $234
CA $287 total
includes taxes & fees
Nov 1 - Nov 2
A cozy, Tuscan-style apartment perfect for families. Pets Allowed
A bedroom with a bed, a vanity with a mirror, and LED strip lighting.

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

Siena Love Nest: Romantic Suite with Spa & Jacuzzi
Toscana
The price is CA $154
CA $272 total
includes taxes & fees
Nov 5 - Nov 6
Siena Love Nest: Romantic Suite with Spa & Jacuzzi
A stone building with a gravel path, outdoor seating, and greenery.

5. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is CA $338
CA $399 total
includes taxes & fees
Nov 2 - Nov 3
The Arch Among the Hills of Castellina
A rustic villa with a garden, a pond, and a mountainous backdrop.

6. Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is CA $13,107
CA $13,115 total
includes taxes & fees
Oct 31 - Nov 1
Ebbio – Villa and Organic Farm in Monteriggioni
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

7. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Are you still available? I want to bring my whole family:)"
United States
Kai
The price is CA $166
CA $189 total
includes taxes & fees
Nov 14 - Nov 15
Agriturismo La Ferrozzola
An open doorway leading to an outdoor area with a bench, a television on a cabinet, and a framed picture on the wall.

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 CA $148
CA $184 total
includes taxes & fees
Nov 5 - Nov 6
Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included
A building with a stone facade, a door, a window, and a patio area with chairs and a table.

9. 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 CA $112
CA $153 total
includes taxes & fees
Nov 11 - Nov 12
A peaceful spot with a garden between Chianti and Crete, near the old town
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 CA $126
CA $248 total
includes taxes & fees
Nov 4 - Nov 5
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 CA $122
CA $142 total
includes taxes & fees
Nov 4 - Nov 5
Casa Vacanze Le Case
A stone building with two windows, one with green shutters, and a rose bush in the foreground.

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 CA $125
CA $219 total
includes taxes & fees
Nov 4 - Nov 5
Exclusive Stone Tower.
A narrow alleyway with a stone archway leading to a building with a brick facade.

13. 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 CA $242
CA $242 total
includes taxes & fees
Nov 5 - Nov 6
A Nest with a View - A Romantic Getaway Within the City Walls
A glass on a wooden surface with a pool and a building in the background.

14. Apartment in Chianti With Pool ID 513

Apartment in Chianti With Pool ID 513
Casole d'Elsa
The price is CA $376
CA $417 total
includes taxes & fees
Oct 31 - Nov 1
Apartment in Chianti With Pool ID 513
A living room with a fireplace, two sofas, a glass coffee table, and a fluffy rug.

15. Vacation in Poggettone

Vacation in Poggettone
Monteroni d'Arbia
The price is CA $225
CA $346 total
includes taxes & fees
Nov 11 - Nov 12
Vacation in Poggettone
A view through a wooden door of a courtyard with stone walls and potted plants.

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 CA $195
CA $282 total
includes taxes & fees
Nov 4 - Nov 5
Chianti Craft House Badia a Passignano
A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

17. 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 CA $78
CA $189 total
includes taxes & fees
Nov 5 - Nov 6
Detached house with a garden, just a few minutes from the Abbey of San Galgano
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 traveller
The price is CA $1,005
CA $1,011 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi
A brick building with a garden, a metal fence, and a clear sky.

19. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $338
CA $422 total
includes taxes & fees
Nov 1 - Nov 2
Casa Marisa in Castellina in Chianti
A narrow stone staircase leading to a door with a glass panel, flanked by brick walls and metal railings.

20. 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 CA $345
CA $394 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi
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

Hotel Athena

Hotel Athena

8/10 Good
"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” port!!"
ALLEN 2-night trip
Posted 1 hour ago
Hotel Athena

Find out more about Siena

Siena Vacation Homes information

Number of reviews
74
Accommodation
132 Vacation Homes
Lowest Price
CA $142
Highest Price
CA $13,115

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