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

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

Siena City Centre

Louise B.

HK$1,622 total

includes taxes & fees

9 Sept - 10 Sept

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

2. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Toscana

HK$1,503 total

includes taxes & fees

20 Sept - 21 Sept

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

3. Cozy Tuscan-style apartment Suitable 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$1,703 total

includes taxes & fees

13 Sept - 14 Sept

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

4. The Arch Among the Hills of Castellina

Topina

HK$2,723 total

includes taxes & fees

4 Oct - 5 Oct

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

5. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$76,538 total

includes taxes & fees

8 Oct - 9 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$965 total

includes taxes & fees

21 Sept - 22 Sept

A stone building with a tiled roof, a central door, and a small courtyard with a fountain.

7. Vana Hills House - Three Bedroom House, Sleeps 8

Monteriggioni

HK$2,145 total

includes taxes & fees

10 Sept - 11 Sept

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

8. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Castelnuovo Berardenga

Anonymous traveller

HK$3,369 total

includes taxes & fees

13 Sept - 14 Sept

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

9. Exclusive Stone Tower.

Casciano

Ryan C.

HK$1,341 total

includes taxes & fees

14 Sept - 15 Sept

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.

10. 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$2,421 total

includes taxes & fees

10 Sept - 11 Sept

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$1,446 total

includes taxes & fees

14 Sept - 15 Sept

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

12. House with pool for 4 pax

Casole d'Elsa

Oliver E.

HK$2,559 total

includes taxes & fees

1 Oct - 2 Oct

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

13. Detached house with garden a few minutes from the abbey of San Galgano

Toscana

Julie M.

HK$1,102 total

includes taxes & fees

10 Sept - 11 Sept

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

14. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,459 total

includes taxes & fees

9 Sept - 10 Sept

A dining area with a table set for four, a large window with an arched ceiling, and a view of the outdoors.

15. La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

casole d'elsa siena

Linda T.

HK$3,306 total

includes taxes & fees

12 Sept - 13 Sept

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

16. Casa Vacanze Le Case

San Gimignano

Jackie

HK$1,170 total

includes taxes & fees

20 Sept - 21 Sept

A rustic wall shelf with a 'PALIO' book and various items.

17. THE CASINA OF SANT 'AGOSTINO

Colle di Val d'Elsa

HK$1,386 total

includes taxes & fees

9 Sept - 10 Sept

A street with outdoor seating, a building with a shop entrance, and a sign with a prohibition symbol.

18. Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Buonconvento

HK$1,209 total

includes taxes & fees

23 Sept - 24 Sept

A swimming pool with a colorful inflatable ring and a water fountain.

19. Farmhouse in Chianti

gaiole in chianti

"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...

Lara W.

HK$4,530 total

includes taxes & fees

13 Sept - 14 Sept

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

20. Holday at Poggettone

Monteroni d'Arbia

HK$2,693 total

includes taxes & fees

6 Oct - 7 Oct

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Top Siena Hotel Reviews

Hotel Chiusarelli

10/10 Excellent

"Great location. Wonderful staff, very helpful and polite."

Hotel Santa Caterina

10/10 Excellent

"Great location just outside the limited traffic zone, and available parking. Staff were very accommodating and friendly. Fantastic breakfast spread with a lovely view of the Tuscan hills. The room was on the smaller side, but more than adequate for one person for a short stay. The a/c worked very well!"

Hotel Minerva

10/10 Excellent

"We would first like to thank Alessandra at the front desk she was so friendly, knowledgeable, informative, friendly, she helped us soo much! The hotel is great, clean, rooms decent size , bathroom is average size , the room and bathroom clean, and the staff was so great and friendly. Great location close to everything, and well maintained. They offered underground parking $20 night, no outside parking. The breakfast was great and the staff so friendly. Great outside area for sitting and breakfast.we had a balcony with amazing views."

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