Siena Holiday Homes from £94: Search Holiday Homes in Siena

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.

includes taxes & fees

29 Sept - 30 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

includes taxes & fees

29 Sept - 30 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.

includes taxes & fees

4 Oct - 5 Oct

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

4. The Arch Among the Hills of Castellina

Topina

includes taxes & fees

1 Oct - 2 Oct

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

5. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

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

includes taxes & fees

1 Oct - 2 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

includes taxes & fees

29 Sept - 30 Sept

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

8. Exclusive Stone Tower.

Casciano

Ryan C.

includes taxes & fees

30 Sept - 1 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.

9. 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.

includes taxes & fees

1 Oct - 2 Oct

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

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

Toscana

Julie M.

includes taxes & fees

1 Oct - 2 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

includes taxes & fees

2 Oct - 3 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.

includes taxes & fees

1 Oct - 2 Oct

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

13. Casa Vacanze Le Case

San Gimignano

Jackie

includes taxes & fees

4 Oct - 5 Oct

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

14. Casa Marisa in Castellina in Chianti

Castellina in Chianti

includes taxes & fees

29 Sept - 30 Sept

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

includes taxes & fees

29 Sept - 30 Sept

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

16. 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.

includes taxes & fees

1 Oct - 2 Oct

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

17. 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

includes taxes & fees

27 Oct - 28 Oct

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

18. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

includes taxes & fees

27 Sept - 28 Sept

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

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

Colle di Val d'Elsa

Anonymous traveller

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

20. Holday at Poggettone

Monteroni d'Arbia

includes taxes & fees

29 Sept - 30 Sept

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Top Siena Hotel Reviews

Il Chiostro del Carmine

10/10 Excellent

"Muy bien ubicado. La llegada en auto es complicada. Hay que coordinar antes de llegar porque no se puede entrar al centro sin permiso. El hotel está bien, buen desayuno y buen personal, el baño buenisimo el tamaño"

Relais La Corte Dei Cavalieri

8/10 Good

"Staff was exceedingly helpful and accommodating. Self check in and Check Out were easy. Staff communicated well, but if you prefer to be left alone, you don't have to interact with anyone at all. Very good for an awkward, anxious North American traveller. Main property, rooms, and hallway were well maintained. I really liked the decor and space provided. However, patio was overgrown, dirty, and unusable except if you need to smoke. Bedding and bathroom were clean; but bed had a corner that sunk and one of the towels had an odd rust stain on it perhaps from the towel rail? I would stay there again if they'd have me. Great value for a last minute nip into Siena for a week."

Find out more about Siena

Siena Holiday Homes information

Number of reviews	81
Accommodation	115 Holiday Homes
Lowest Price	£94
Highest Price	£7,227

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Siena holiday homes

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

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

3. Cozy Tuscan-style apartment Suitable for families. Pets allowed

4. The Arch Among the Hills of Castellina

5. Ebbio – Villa and Organic Farm in Monteriggioni

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

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

8. Exclusive Stone Tower.

9. Casa Crevole di Martina in the Heart of Tuscany

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

11. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

12. House with pool for 4 pax

13. Casa Vacanze Le Case

14. Casa Marisa in Castellina in Chianti

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

16. Farmhouse in Chianti

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

18. Chianti Craft House Badia a Passignano

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

20. Holday at Poggettone

Find holiday rentals that suit your style

Top Siena Hotel Reviews

Il Chiostro del Carmine

Hotel Chiusarelli

Hotel Athena

Villa Ermellina Siena, a Tribute Portfolio Hotel

Relais La Corte Dei Cavalieri

Piccolo Hotel Etruria

Siena Vip

Best Western Hotel San Marco

Hotel Alma Domus

Find out more about Siena

Siena Holiday Homes information

Explore a world of travel with Expedia