Siena Vacation Homes

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

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Our top choices for Siena holiday homes

A historic building with a statue on the steps, a wooden door, and a brick facade.

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

Siena City Centre

Louise B.

HK$1,354 total

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with white cabinets, a built-in oven, and a large window.

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

Siena City Centre

Phil S.

HK$1,002 total

includes taxes & fees

27 Oct - 28 Oct

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$1,644 total

includes taxes & fees

24 Oct - 25 Oct

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$1,547 total

includes taxes & fees

26 Oct - 27 Oct

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

5. The Arch Among the Hills of Castellina

Topina

HK$2,453 total

includes taxes & fees

3 Nov - 4 Nov

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

6. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$73,901 total

includes taxes & fees

27 Oct - 28 Oct

A stone building with multiple windows and a chimney.

7. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

HK$1,142 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Casetta

HK$862 total

includes taxes & fees

2 Nov - 3 Nov

9. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

Monteroni d'Arbia

HK$1,038 total

includes taxes & fees

27 Oct - 28 Oct

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

10. Exclusive Stone Tower.

Casciano

Ryan C.

HK$1,232 total

includes taxes & fees

27 Oct - 28 Oct

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

11. 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$1,396 total

includes taxes & fees

26 Oct - 27 Oct

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

12. Casa Vacanze Le Case

San Gimignano

Andrew

HK$837 total

includes taxes & fees

2 Nov - 3 Nov

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

13. House with pool for 4 pax

Pievescola

Judith C.

HK$2,422 total

includes taxes & fees

25 Oct - 26 Oct

A rural property with a stone building, a dirt path leading to it, and surrounding olive trees.

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

Castelnuovo Berardenga

Anonymous traveller

HK$5,698 total

includes taxes & fees

2 Nov - 3 Nov

A traditional stone building with a tiled roof, surrounded by terraced fields and mountains in the background.

15. A Nest with a View - A Romantic Retreat Within the City Walls

Radicondoli

HK$1,365 total

includes taxes & fees

2 Nov - 3 Nov

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

16. Apartment in Chianti With Pool ID 513

Casole d'Elsa

HK$2,351 total

includes taxes & fees

29 Oct - 30 Oct

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

17. Vacation in Poggettone

Monteroni d'Arbia

HK$1,952 total

includes taxes & fees

29 Oct - 30 Oct

A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

18. Detached house with a garden, just a few minutes from the Abbey of San Galgano

Toscana

Julie M.

HK$1,064 total

includes taxes & fees

24 Oct - 25 Oct

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

19. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,374 total

includes taxes & fees

25 Oct - 26 Oct

A balcony with a tiled roof, a table with chairs, and a guitar leaning against the wall.

20. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

Poggiobrucoli

HK$2,223 total

includes taxes & fees

2 Nov - 3 Nov

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Top Siena Hotel Reviews

NH Siena

10/10 Excellent

"The room isn't cleaned too well. There were some crumbs that were attracting ants. Other than that- no issues"

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."

Villa Ermellina Siena, a Tribute Portfolio Hotel

8/10 Good

"We were in one of the other wings so it wasn't in the main building. It was a rainy week and we had a wedding and there were no rooms in the main building to accommodate us. There is no overhead so you will get wet and there are a million stairs to get to that wing (you will need help if you have a ton of luggage as well). The hotel is far from city center too, you need to plan your cabs out accordingly."

Find out more about Siena