Siena Holiday Homes from €110: Search Top House Rentals

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

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

Toscana

includes taxes & fees

21 Sept - 22 Sept

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.

includes taxes & fees

23 Aug - 24 Aug

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

3. The Arch Among the Hills of Castellina

Topina

includes taxes & fees

21 Sept - 22 Sept

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

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

Casetta

includes taxes & fees

14 Sept - 15 Sept

A stone building with a tiled roof, a central door, and a small courtyard with a fountain.

5. Vana Hills House - Three Bedroom House, Sleeps 8

Monteriggioni

includes taxes & fees

25 Aug - 26 Aug

A well-lit garden at night with a large moon in the sky, various potted plants, and a neatly trimmed lawn.

6. Villa with large garden in the Chianti hills

Siena

Julie H.

includes taxes & fees

7 Sept - 8 Sept

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

21 Sept - 22 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

22 Sept - 23 Sept

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

9. House with pool for 4 pax

Casole d'Elsa

Oliver E.

includes taxes & fees

21 Sept - 22 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

24 Aug - 25 Aug

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

23 Aug - 24 Aug

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

12. 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

24 Aug - 25 Aug

A spacious living room with leather sofas, a fireplace, and a kitchen in the background.

13. Casa Marisa in Castellina in Chianti

Castellina in Chianti

includes taxes & fees

20 Sept - 21 Sept

A clear blue pool with a view of green hills and a distant building.

14. Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

Rosennano

includes taxes & fees

31 Aug - 1 Sept

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

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

casole d'elsa siena

Linda T.

includes taxes & fees

12 Sept - 13 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

13 Sept - 14 Sept

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

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

Buonconvento

includes taxes & fees

14 Sept - 15 Sept

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

18. Casa Vacanze Le Case

San Gimignano

Jackie

includes taxes & fees

28 Aug - 29 Aug

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

19. Chianti Craft House Badia a Passignano

Barberino Tavarnelle

Oscar O.

includes taxes & fees

23 Aug - 24 Aug

A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

20. Agritourism in val d'orcia

montalcino

includes taxes & fees

23 Aug - 24 Aug

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Top Siena Hotel Reviews

Hotel Chiusarelli

10/10 Excellent

"The staff were very helpful with my questions. I had a room on the lower floor during a heat wave and the room stayed cool. The bathroom was clean and there was even a nice little balcony."

Il Chiostro del Carmine

10/10 Excellent

"A delight in every aspect—beautiful entrance and grounds, charming, helpful and friendly staff, grand staircase to our large room with high ceilings, and a full breakfast buffet both Italian and American style). Great location for the main sights, but a quiet neighborhood when they are not celebrating the Palio. Highly recommend choosing this place."

Hotel Athena

10/10 Excellent

"We had a superior room, which was very comfortable. We had dinner in the restaurant several times, and the food and drink was excellent. One evening we just enjoyed the cocktail bar, and the staff were fun! Breakfast buffet has everything one could want, and was always fresh. Free parking! You will have an uphill walk to the town centre, but no matter where you go in Siena it’s either up or down. Highly recommended."

Hotel Santa Caterina

10/10 Excellent

"Hotel was located just outside of the gates to sienna. Half of our group walked to the center of town and half of our group took a taxi. The hotel called the taxi for us. The check-in was easy and the night person also ran the bar. We took our drinks out to the back patio area, which had a wonderful view of the city both night and daytime. Rooms were two levels. Ours had a bed downstairs with the bathroom and then a steeper staircase to a loft area with another two beds. It worked out fine. It is a very old building centuries old, which has been peacefully redone with antique accents. Yes I would stay here again."

Find out more about Siena

Siena Holiday Homes information

Number of reviews	195
Accommodation	115 Holiday Homes
Lowest Price	€110
Highest Price	€744

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Siena holiday homes

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

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

3. The Arch Among the Hills of Castellina

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

5. Vana Hills House - Three Bedroom House, Sleeps 8

6. Villa with large garden in the Chianti hills