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

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

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

includes taxes & fees

29 Sept - 30 Sept

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.

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

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

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.

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

Casetta

includes taxes & fees

28 Sept - 29 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

27 Sept - 28 Sept

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

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

Castelnuovo Berardenga

Anonymous traveller

includes taxes & fees

29 Sept - 30 Sept

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

29 Sept - 30 Sept

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.

11. 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

30 Sept - 1 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 small brick structure with an arched entrance, surrounded by gravel, potted plants, and trees.

13. Holday at Poggettone

Monteroni d'Arbia

includes taxes & fees

28 Sept - 29 Sept

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

includes taxes & fees

30 Sept - 1 Oct

A street with outdoor seating, a building with a shop entrance, and a sign with a prohibition symbol.

15. Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Buonconvento

includes taxes & fees

28 Sept - 29 Sept

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

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

Radicondoli

includes taxes & fees

29 Sept - 30 Sept

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

17. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

includes taxes & fees

27 Sept - 28 Sept

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

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

casole d'elsa siena

Linda T.

includes taxes & fees

9 Oct - 10 Oct

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

19. 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.

20. Casa Marisa in Castellina in Chianti

Castellina in Chianti

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	116
Accommodation	115 Holiday Homes
Lowest Price	£94
Highest Price	£7,227

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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. 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

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

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

5. The Arch Among the Hills of Castellina

6. Ebbio – Villa and Organic Farm in Monteriggioni

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

8. Exclusive Stone Tower.

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

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

11. Casa Crevole di Martina in the Heart of Tuscany

12. House with pool for 4 pax

13. Holday at Poggettone

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

15. Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

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

17. Chianti Craft House Badia a Passignano

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

19. Casa Vacanze Le Case

20. Casa Marisa in Castellina in Chianti

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

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