Siena Vacation Home Rentals from CA $142: Search Top Private Vacation Homes for Rent

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Siena vacation homes

A stone building with a sign reading "VIA DI CALZOLERIA".

1. IL TOLOMEI - new apartment in the middle of the main street

Siena City Centre

Louise B.

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

Siena City Centre

Phil S.

A rustic building with a brick facade, a small arched window, and a door.

3. A cozy, Tuscan-style apartment perfect for families. Pets Allowed

Toscana

"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."

Shanti R.

CA $288 total

includes taxes & fees

Oct 28 - Oct 29

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

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

Toscana

CA $272 total

includes taxes & fees

Nov 3 - Nov 4

A stone building with a gravel path, outdoor seating, and greenery.

5. The Arch Among the Hills of Castellina

Topina

CA $399 total

includes taxes & fees

Nov 3 - Nov 4

A rustic villa with a garden, a pond, and a mountainous backdrop.

6. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

CA $13,162 total

includes taxes & fees

Nov 3 - Nov 4

A building with a stone facade, a door, a window, and a patio area with chairs and a table.

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

Casetta

CA $153 total

includes taxes & fees

Nov 10 - Nov 11

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

8. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

CA $201 total

includes taxes & fees

Nov 8 - Nov 9

An open doorway leading to an outdoor area with a bench, a television on a cabinet, and a framed picture on the wall.

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

Monteroni d'Arbia

CA $185 total

includes taxes & fees

Nov 23 - Nov 24

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

Ruffoli

"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...

James

CA $249 total

includes taxes & fees

Oct 29 - Oct 30

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

11. Casa Vacanze Le Case

San Gimignano

Andrew

CA $142 total

includes taxes & fees

Nov 3 - Nov 4

A stone building with two windows, one with green shutters, and a rose bush in the foreground.

12. Exclusive Stone Tower.

Casciano

Ryan C.

CA $219 total

includes taxes & fees

Nov 3 - Nov 4

A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

13. Apartment in Chianti With Pool ID 513

Casole d'Elsa

CA $419 total

includes taxes & fees

Oct 28 - Oct 29

A balcony with a view of a stone building and surrounding landscape.

14. A Nest with a View - A Romantic Getaway Within the City Walls

Radicondoli

CA $243 total

includes taxes & fees

Nov 3 - Nov 4

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and greenery.

15. House with pool for 4 pax

Pievescola

Judith C.

A rectangular swimming pool with a wooden deck and metal railings, surrounded by a grassy area with trees and a clear sky.

16. Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi

Castelnuovo Berardenga

Anonymous traveller

CA $1,015 total

includes taxes & fees

Nov 3 - Nov 4

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

Toscana

Julie M.

CA $189 total

includes taxes & fees

Nov 5 - Nov 6

A small brick structure with an arched entrance, surrounded by gravel, potted plants, and trees.

18. Vacation in Poggettone

Monteroni d'Arbia

CA $345 total

includes taxes & fees

Oct 28 - Oct 29

A two-story house with a stone foundation, wooden shutters, and a covered porch with outdoor furniture.

19. Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

Casole d'Elsa

Anonymous traveller

CA $697 total

includes taxes & fees

Nov 3 - Nov 4

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

Poggiobrucoli

CA $396 total

includes taxes & fees

Nov 3 - Nov 4

View all properties

Find vacation rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Siena Hotel Reviews

Hotel Minerva

10/10 Excellent

"Clean, great breakfast, lovely view!"

Hotel Italia

10/10 Excellent

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."

Find out more about Siena

Siena Vacation Homes information

Number of reviews	66
Accommodation	132 Vacation Homes
Lowest Price	CA $142
Highest Price	CA $13,162

Explore a world of travel with Expedia

Book Vacation Homes in Siena on Expedia.it

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Siena vacation homes

1. IL TOLOMEI - new apartment in the middle of the main street

2. CASA ILARIA - Bright apartment with a view in the historic center

3. A cozy, Tuscan-style apartment perfect for families. Pets Allowed

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

5. The Arch Among the Hills of Castellina

6. Ebbio – Villa and Organic Farm in Monteriggioni