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

1. 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

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

2. 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$1,635 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Toscana

HK$1,547 total

includes taxes & fees

18 Oct - 19 Oct

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

4. The Arch Among the Hills of Castellina

Topina

HK$2,452 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$73,879 total

includes taxes & fees

12 Oct - 13 Oct

A stone building with multiple windows and a chimney.

6. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

HK$1,142 total

includes taxes & fees

8 Nov - 9 Nov

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

A concrete outdoor grill with a metal grate and a metal handle.

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

Monteroni d'Arbia

HK$1,037 total

includes taxes & fees

23 Oct - 24 Oct

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

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

Casetta

HK$861 total

includes taxes & fees

9 Nov - 10 Nov

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$1,231 total

includes taxes & fees

12 Oct - 13 Oct

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

11. Casa Vacanze Le Case

San Gimignano

Andrew

HK$837 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.

12. 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$4,269 total

includes taxes & fees

8 Nov - 9 Nov

A stone building with a tiled roof, surrounded by lush greenery and a wooden pergola.

13. Apartment in Chianti With Pool ID 450

Casole d'Elsa

HK$3,898 total

includes taxes & fees

12 Oct - 13 Oct

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

14. 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$1,395 total

includes taxes & fees

12 Oct - 13 Oct

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

15. Farmhouse in Chianti

gaiole in chianti

"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."

Johanna K.

HK$4,373 total

includes taxes & fees

12 Oct - 13 Oct

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

16. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,373 total

includes taxes & fees

14 Oct - 15 Oct

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

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

Toscana

Julie M.

HK$1,064 total

includes taxes & fees

12 Oct - 13 Oct

A bedroom with a stone wall, a bed with pink bedding, a green chair, a small table with a lamp, and a bookshelf.

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

Poggiobrucoli

HK$2,222 total

includes taxes & fees

2 Nov - 3 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.

19. 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$2,240 total

includes taxes & fees

13 Oct - 14 Oct

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

20. House with pool for 4 pax

Pievescola

Oliver E.

HK$2,422 total

includes taxes & fees

12 Oct - 13 Oct

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Top Siena Hotel Reviews

Villa Scacciapensieri Boutique Hotel

8/10 Good

"Very helpful staff with easy access to Siena by local buses. Good variety of breakfast items. Quiet location."

Il Chiostro del Carmine

10/10 Excellent

"Great breakfast, stunning views of the Tuscan countryside and felt like walking into the past. Exactly as per the photos, a wonderful ambience, full of charm and character. Well located on the edge of the old town, less than 10 minutes walk to the centre. The staff were so friendly and helpful. I would not hesitate to recommend this hotel and hope to come back myself."

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