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$1,426 total

includes taxes & fees

29 Sept - 30 Sept

A brick building with a sliding glass door entrance, a large potted plant, and two smaller potted plants outside.

2. GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

Siena

HK$1,334 total

includes taxes & fees

23 Sept - 24 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$1,682 total

includes taxes & fees

2 Oct - 3 Oct

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

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

Toscana

HK$1,586 total

includes taxes & fees

27 Sept - 28 Sept

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

5. The Arch Among the Hills of Castellina

Topina

HK$2,694 total

includes taxes & fees

1 Oct - 2 Oct

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

6. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$75,728 total

includes taxes & fees

8 Oct - 9 Oct

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

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

Castelnuovo Berardenga

Anonymous traveller

HK$3,438 total

includes taxes & fees

23 Sept - 24 Sept

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

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

Casetta

HK$953 total

includes taxes & fees

22 Oct - 23 Oct

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

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

Casole d'Elsa

"Pros: Das Haus ist liebevoll eingerichtet, hat zwei schöne Bäder und eine wunderbare schattige Terrasse, von der man ins Grüne schaut, tagsüber ab und zu die Schafe nebenan und abends die Wildschweine hören kann. Das Haus liegt sehr ruhig in einem abgeschiedenen Weiler. Es sind ausreichend Liegestühle vorhanden, um im Garten zu entspannen. Die Klimaanlage im Haus funktioniert bestens. Besonders hervorzuheben sind die sehr herzlichen und hilfsbereiten Vermieter, die auch in dem kleinen Ort wohnen...

Anonymous traveller

HK$4,672 total

includes taxes & fees

12 Oct - 13 Oct

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$2,395 total

includes taxes & fees

23 Sept - 24 Sept

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$1,260 total

includes taxes & fees

23 Sept - 24 Sept

A clear blue pool with a view of green hills and a distant building.

12. Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

Rosennano

HK$3,442 total

includes taxes & fees

24 Sept - 25 Sept

A table set outdoors with fruits, a pitcher of red drink, and a vase of flowers.

13. Holiday Home 'Rustico Con Jacuzzi In Toscana' with Shared Pool, Wi-Fi and Air Conditioning

Colle di Val d'Elsa

Anonymous traveller

HK$2,919 total

includes taxes & fees

24 Sept - 25 Sept

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

14. House with pool for 4 pax

Pievescola

Oliver E.

HK$2,564 total

includes taxes & fees

2 Oct - 3 Oct

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

15. 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$4,482 total

includes taxes & fees

27 Sept - 28 Sept

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

16. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,433 total

includes taxes & fees

23 Sept - 24 Sept

A covered patio with a wooden table and chairs, stone walls, and a view of a garden.

17. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

Anonymous traveller

HK$3,566 total

includes taxes & fees

24 Sept - 25 Sept

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

18. Casa Vacanze Le Case

San Gimignano

Jackie

HK$1,156 total

includes taxes & fees

4 Oct - 5 Oct

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

19. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

HK$1,631 total

includes taxes & fees

24 Sept - 25 Sept

A stone building with a blue door, a wicker basket, and a clear vase with pink flowers.

20. Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi

Colle Val d'Elsa

Rupert H.

HK$3,666 total

includes taxes & fees

30 Sept - 1 Oct

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Top Siena Hotel Reviews

Best Western Hotel San Marco

10/10 Excellent

"Property was clean and comfortable. Enjoyed our stay"

Piccolo Hotel Etruria

10/10 Excellent

"The hotel was very close to the plaza El Campo. The one night we ate in the plaza there was a celebration, which was wonderful to observe, while we were eating our dinner in a wonderful restaurant. Food was excellent service was excellent. The Central city of Siena was fun to experience with narrow passages and lots to see."

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good

"Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty."

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