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$1,456 total

includes taxes & fees

5 Oct - 6 Oct

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$1,652 total

includes taxes & fees

4 Oct - 5 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$1,554 total

includes taxes & fees

7 Oct - 8 Oct

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

4. The Arch Among the Hills of Castellina

Topina

HK$2,411 total

includes taxes & fees

5 Oct - 6 Oct

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

5. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$74,235 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$866 total

includes taxes & fees

2 Nov - 3 Nov

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$1,042 total

includes taxes & fees

13 Oct - 14 Oct

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

8. Exclusive Stone Tower.

Casciano

Ryan C.

HK$1,237 total

includes taxes & fees

5 Oct - 6 Oct

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$1,402 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$3,442 total

includes taxes & fees

8 Oct - 9 Oct

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

11. House with pool for 4 pax

Pievescola

Oliver E.

HK$2,433 total

includes taxes & fees

4 Oct - 5 Oct

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

12. Casa Vacanze Le Case

San Gimignano

Andrew

HK$841 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Radicondoli

HK$1,252 total

includes taxes & fees

1 Nov - 2 Nov

A glass on a wooden table with a pool and a building in the background.

14. Apartment in Chianti With Pool ID 513

Casole d'Elsa

HK$2,227 total

includes taxes & fees

4 Oct - 5 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.

15. 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$2,251 total

includes taxes & fees

4 Oct - 5 Oct

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

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

Toscana

Julie M.

HK$1,069 total

includes taxes & fees

4 Oct - 5 Oct

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

17. Holday at Poggettone

Monteroni d'Arbia

HK$1,961 total

includes taxes & fees

5 Oct - 6 Oct

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

18. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,385 total

includes taxes & fees

11 Oct - 12 Oct

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

19. 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$4,195 total

includes taxes & fees

12 Oct - 13 Oct

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

20. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

HK$1,599 total

includes taxes & fees

5 Oct - 6 Oct

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Top Siena Hotel Reviews

Piccolo Hotel Etruria

10/10 Excellent

"Great location near the plaza and many stores/restaurants. Everything works except for in room safe. No electric kettle even though I requested it. Good grocery store and coffee shop only steps away. Located in historic area and building. Big triple room and quiet setting and nice lounge on second floor. AC works well. I recommend this place and will stay there again. Richard from Canada."

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"This hotel was PERFECT for our honeymoon trip to Siena. It was peaceful and quiet, but still close enough to get to the city centre and the train station easily. The pool was a perfect oasis after hot days. The staff were so friendly and helpful. The terrace was a gorgeous place for a night cap at the end of the night. We would definitely stay here again."

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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