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

1. THE TOLOMEI - apartment in the heart of the main street

Siena City Centre

Louise B.

A horse grazing under a tree in a grassy area with a small building in the background.

2. 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$1,648 total

includes taxes & fees

22 Oct - 23 Oct

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

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

Toscana

HK$1,551 total

includes taxes & fees

26 Oct - 27 Oct

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

4. The Arch Among the Hills of Castellina

Topina

HK$2,459 total

includes taxes & fees

2 Nov - 3 Nov

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

5. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$74,069 total

includes taxes & fees

27 Oct - 28 Oct

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

6. Peaceful corner with garden between Chianti and Crete, very close to Old Town

Casetta

HK$864 total

includes taxes & fees

2 Nov - 3 Nov

A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

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

Monteroni d'Arbia

HK$1,040 total

includes taxes & fees

22 Oct - 23 Oct

A stone building with multiple windows and a chimney.

8. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

HK$1,144 total

includes taxes & fees

8 Nov - 9 Nov

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

9. 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$1,399 total

includes taxes & fees

23 Oct - 24 Oct

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

10. Casa Vacanze Le Case

San Gimignano

Andrew

HK$839 total

includes taxes & fees

2 Nov - 3 Nov

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

11. Exclusive Stone Tower.

Casciano

Ryan C.

HK$1,235 total

includes taxes & fees

22 Oct - 23 Oct

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

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

Castelnuovo Berardenga

Anonymous traveller

HK$5,710 total

includes taxes & fees

3 Nov - 4 Nov

A two-story building with a stone facade and a tiled roof.

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

Radicondoli

HK$1,368 total

includes taxes & fees

1 Nov - 2 Nov

A rustic outdoor setting with a stone building, a wooden table with chairs, a brick oven, and a variety of greenery including tall cypress trees and flowering plants.

14. Casa Crevole di Martina in the Heart of Tuscany

Murlo

"Nach einer herzlichen Begrüßung durch die Gastgeberin haben wir ein paar entspannte Tage verbracht. Im Kühlschrank befanden sich für uns schon einmal keiner Erfrischungen. Obwohl wir nur 4 Nächte blieben, gab es einen Handtuchtausch nach 2 Tagen. Total überrascht hat uns aber der selbstgebackene Kuchen der für uns bereit stand. Wir würden hier jeder Zeit wieder Urlaub machen und können die Unterkunft mehr wir nur empehlen."

Sybille F.

HK$2,246 total

includes taxes & fees

25 Oct - 26 Oct

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.

HK$2,428 total

includes taxes & fees

22 Oct - 23 Oct

A stone bench with a rustic fire pit in a garden setting.

16. Apartment in Chianti With Pool ID 513

Casole d'Elsa

HK$2,356 total

includes taxes & fees

22 Oct - 23 Oct

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

17. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,379 total

includes taxes & fees

25 Oct - 26 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$1,066 total

includes taxes & fees

22 Oct - 23 Oct

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

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

Poggiobrucoli

HK$2,228 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Casole d'Elsa

Anonymous traveller

HK$4,186 total

includes taxes & fees

25 Oct - 26 Oct

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Top Siena Hotel Reviews

Il Chiostro del Carmine

8/10 Good

"Breakfast"

Siena Vip

8/10 Good

"Room was clean. Excellent service. As with most cities in Italy, this is slightly in ZTL zone so had to park, walk up hill, check in, walk back down hill, and move car. The hostess helps you register rental car for the ZTL so you can park closer. To see main Sienna, there is an escalator nearby so you can ride to the top."

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."

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