Siena Holiday Homes from £95: 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

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

Toscana

includes taxes & fees

20 Aug - 21 Aug

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

21 Aug - 22 Aug

3. The Arch Among the Hills of Castellina

Topina

includes taxes & fees

10 Sept - 11 Sept

4. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

includes taxes & fees

16 Aug - 17 Aug

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

Casetta

includes taxes & fees

3 Sept - 4 Sept

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

Monteriggioni

includes taxes & fees

27 Aug - 28 Aug

7. Villa with large garden in the Chianti hills

Siena

Julie H.

includes taxes & fees

2 Sept - 3 Sept

8. Exclusive Stone Tower.

Casciano

Ryan C.

includes taxes & fees

28 Aug - 29 Aug

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

includes taxes & fees

13 Aug - 14 Aug

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

Toscana

includes taxes & fees

12 Sept - 13 Sept

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

Castelnuovo Berardenga

Anonymous traveller

includes taxes & fees

11 Sept - 12 Sept

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

Buonconvento

includes taxes & fees

13 Aug - 14 Aug

13. Casa Vacanze Le Case

San Gimignano

Jackie

includes taxes & fees

28 Aug - 29 Aug

14. House with pool for 4 pax

Casole d'Elsa

Oliver E.

includes taxes & fees

4 Sept - 5 Sept

15. Casa Marisa in Castellina in Chianti

Castellina in Chianti

includes taxes & fees

19 Aug - 20 Aug

16. Chianti Craft House Badia a Passignano

Barberino Tavarnelle

Oscar O.

includes taxes & fees

25 Aug - 26 Aug

17. 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

28 Aug - 29 Aug

18. Agritourism in val d'orcia

montalcino

includes taxes & fees

13 Aug - 14 Aug

19. 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

2 Sept - 3 Sept

20. Holday at Poggettone

Monteroni d'Arbia

includes taxes & fees

24 Aug - 25 Aug

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Top Siena Hotel Reviews

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent

"My husband and I fully enjoyed our stay at the Villa Ermellina. We had a room near the gym, spacious and convenient. Much space to move around, a table with 2 chairs and a very large bathroom. Sufficient closet space as well. Dining on the property offers a wonderful terrasse for breakfast or any meal, but meals are pricey. We still greatly enjoyed our choices. The pool area is certainly a big attraction to this wonderfully located property in Sienna. This completed our vacation feel in Tuscany."

Hotel Alma Domus

10/10 Excellent

"The history of the hotel and its location is special, access is adjacent to famous historical Saint Catherine Church, with an exceptional view of the World Famous Cathedral Duomo de Siena!! The room and breakfast are fantastic for the very reasonable price! t's just outside the historical Piazza del Campo, walkable and truly enjoyable experience with multiple up stepping!!!"

Hotel Chiusarelli

8/10 Good

"Location was great - 5 mins to the bus station and town centre. Staff were friendly and helpful. Room was comfortable. Only issue we faced was with the hairdryer - attached to the wall in the bathroom - it kept cutting out. Luckily one of the team were able to bring a portable one - but was a bit of a pain. Would defo recommend if you are in Siena."

Find out more about Siena

Siena Holiday Homes information

Number of reviews	126
Accommodation	95 Holiday Homes
Lowest Price	£95
Highest Price	£3,555

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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. Ebbio – Villa and Organic Farm in Monteriggioni

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

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

7. Villa with large garden in the Chianti hills

8. Exclusive Stone Tower.

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

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

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

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

13. Casa Vacanze Le Case

14. House with pool for 4 pax

15. Casa Marisa in Castellina in Chianti

16. Chianti Craft House Badia a Passignano

17. Casa Crevole di Martina in the Heart of Tuscany

18. Agritourism in val d'orcia

19. Farmhouse in Chianti

20. Holday at Poggettone

Find holiday rentals that suit your style

Top Siena Hotel Reviews

Villa Ermellina Siena, a Tribute Portfolio Hotel

Palazzo Ravizza

Hotel Alma Domus

Hotel Italia

Hotel Athena

Hotel Chiusarelli

Il Chiostro del Carmine

Villa Scacciapensieri Boutique Hotel

Piccolo Hotel Etruria

Find out more about Siena

Siena Holiday Homes information

Explore a world of travel with Expedia