Siena Vacation Homes

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 holiday 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

Siena City Centre

Louise B.

HK$1,347 total

includes taxes & fees

2 Nov - 3 Nov

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.

HK$997 total

includes taxes & fees

5 Nov - 6 Nov

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

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.

HK$1,632 total

includes taxes & fees

31 Oct - 1 Nov

A bedroom with a bed, a vanity with a mirror, and LED strip lighting.

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

Toscana

HK$1,536 total

includes taxes & fees

2 Nov - 3 Nov

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

5. The Arch Among the Hills of Castellina

Topina

HK$2,226 total

includes taxes & fees

2 Nov - 3 Nov

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

6. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$73,366 total

includes taxes & fees

30 Oct - 31 Oct

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

7. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

HK$1,134 total

includes taxes & fees

8 Nov - 9 Nov

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

Monteroni d'Arbia

HK$1,030 total

includes taxes & fees

30 Oct - 31 Oct

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

Casetta

HK$855 total

includes taxes & fees

2 Nov - 3 Nov

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

HK$1,386 total

includes taxes & fees

30 Oct - 31 Oct

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

11. Casa Vacanze Le Case

San Gimignano

Andrew

HK$792 total

includes taxes & fees

5 Nov - 6 Nov

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

12. Exclusive Stone Tower.

Casciano

Ryan C.

HK$1,223 total

includes taxes & fees

31 Oct - 1 Nov

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

Radicondoli

HK$1,358 total

includes taxes & fees

10 Nov - 11 Nov

A glass on a wooden surface with a pool and a building in the background.

14. Apartment in Chianti With Pool ID 513

Casole d'Elsa

HK$2,334 total

includes taxes & fees

30 Oct - 31 Oct

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

15. Vacation in Poggettone

Monteroni d'Arbia

HK$1,938 total

includes taxes & fees

30 Oct - 31 Oct

A view through a wooden door of a courtyard with stone walls and potted plants.

16. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

HK$1,597 total

includes taxes & fees

2 Nov - 3 Nov

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.

HK$1,056 total

includes taxes & fees

31 Oct - 1 Nov

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

Castelnuovo Berardenga

Anonymous traveller

HK$5,656 total

includes taxes & fees

2 Nov - 3 Nov

A brick building with a garden, a metal fence, and a clear sky.

19. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,357 total

includes taxes & fees

2 Nov - 3 Nov

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

HK$2,207 total

includes taxes & fees

2 Nov - 3 Nov

View all properties

Find holiday 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

Il Chiostro del Carmine

10/10 Excellent

"Everything about this place is excellent. We had a wonderful stay and beautiful views of the sunrise! One thing to note is that you do have to take a flight of stairs to your room as there is no elevator. If you have luggage you may want to take this into consideration. We did and it was manageable!"

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