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$1,455 total

includes taxes & fees

5 Oct - 6 Oct

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$1,489 total

includes taxes & fees

6 Oct - 7 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$1,553 total

includes taxes & fees

7 Oct - 8 Oct

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

4. 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$1,650 total

includes taxes & fees

4 Oct - 5 Oct

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

5. The Arch Among the Hills of Castellina

Topina

HK$2,409 total

includes taxes & fees

5 Oct - 6 Oct

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

6. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$74,155 total

includes taxes & fees

8 Oct - 9 Oct

A bedroom with a bed, a chair, a nightstand, a lamp, a decorative headboard, and a window with curtains.

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

Monteroni d'Arbia

HK$1,041 total

includes taxes & fees

29 Oct - 30 Oct

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$865 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.

9. Exclusive Stone Tower.

Casciano

Ryan C.

HK$1,236 total

includes taxes & fees

5 Oct - 6 Oct

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

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

Castelnuovo Berardenga

Anonymous traveller

HK$3,438 total

includes taxes & fees

8 Oct - 9 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$1,401 total

includes taxes & fees

5 Oct - 6 Oct

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

12. House with pool for 4 pax

Pievescola

Oliver E.

HK$2,431 total

includes taxes & fees

5 Oct - 6 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$1,068 total

includes taxes & fees

3 Oct - 4 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.

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$2,266 total

includes taxes & fees

4 Oct - 5 Oct

A balcony with potted plants and a view of rolling hills and mountains.

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

Radicondoli

HK$1,251 total

includes taxes & fees

1 Nov - 2 Nov

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

16. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,382 total

includes taxes & fees

11 Oct - 12 Oct

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

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

casole d'elsa siena

Linda T.

HK$2,898 total

includes taxes & fees

9 Oct - 10 Oct

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

18. 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$4,284 total

includes taxes & fees

2 Nov - 3 Nov

A dining area with a table set for four, an arched doorway, and a kitchen visible through the doorway.

19. Holday at Poggettone

Monteroni d'Arbia

HK$1,959 total

includes taxes & fees

5 Oct - 6 Oct

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

20. 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$4,380 total

includes taxes & fees

5 Oct - 6 Oct

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Top Siena Hotel Reviews

Piccolo Hotel Etruria

8/10 Good

"Helpful friendly staff and lovely area Bathroom didn’t have soap and toothpaste but other than that it was a cosy comfortable stay"

Hotel Alma Domus

8/10 Good

"The hotel is right in the historic site and as a result there was a very short walk to see the main piazza and attractions. Trying to find parking outside of the restricted vehicle access points was a total frustrating nightmare. The directions we were given to find free parking turned out to be metered parking and our vehicle would have had have been moved before midnight. Luckily we were directed by a local resident where the free parking was but we had to wait over an hour for a spot to open. The walk back to the the hotel was over 400 meters and it was very busy with tourists. The room was small but clean. The male receptionist we dealt with upon arrival was very short and not friendly. His replacement worker was much more accommodating and friendlier. The most frustrating part was trying to find parking. We went in September which was not even the peak season so good luck with the parking if you go."

Hotel Certosa Di Maggiano

10/10 Excellent

"Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc. The property was beautiful, maintained nicely, and was very quiet. Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!"

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