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

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

Toscana

HK$1,492 total

includes taxes & fees

29 Aug - 30 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.

HK$1,702 total

includes taxes & fees

22 Aug - 23 Aug

3. The Arch Among the Hills of Castellina

Topina

HK$3,286 total

includes taxes & fees

31 Aug - 1 Sept

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

Casetta

HK$970 total

includes taxes & fees

14 Sept - 15 Sept

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

Monteriggioni

HK$2,261 total

includes taxes & fees

25 Aug - 26 Aug

6. Villa with large garden in the Chianti hills

Siena

Julie H.

HK$1,263 total

includes taxes & fees

1 Sept - 2 Sept

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

Castelnuovo Berardenga

Anonymous traveller

HK$3,387 total

includes taxes & fees

22 Aug - 23 Aug

8. Exclusive Stone Tower.

Casciano

Ryan C.

HK$1,449 total

includes taxes & fees

26 Aug - 27 Aug

9. House with pool for 4 pax

Casole d'Elsa

Oliver E.

HK$2,703 total

includes taxes & fees

21 Sept - 22 Sept

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

Toscana

Julie M.

HK$1,108 total

includes taxes & fees

24 Aug - 25 Aug

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.

HK$2,434 total

includes taxes & fees

23 Aug - 24 Aug

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

HK$1,471 total

includes taxes & fees

24 Aug - 25 Aug

13. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,471 total

includes taxes & fees

24 Aug - 25 Aug

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

Rosennano

HK$2,327 total

includes taxes & fees

22 Aug - 23 Aug

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

casole d'elsa siena

Linda T.

HK$3,350 total

includes taxes & fees

12 Sept - 13 Sept

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.

HK$4,599 total

includes taxes & fees

1 Sept - 2 Sept

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

Buonconvento

HK$1,215 total

includes taxes & fees

14 Sept - 15 Sept

18. Casa Vacanze Le Case

San Gimignano

Jackie

HK$1,176 total

includes taxes & fees

28 Aug - 29 Aug

19. Chianti Craft House Badia a Passignano

Barberino Tavarnelle

Oscar O.

HK$1,675 total

includes taxes & fees

23 Aug - 24 Aug

20. Agritourism in val d'orcia

montalcino

HK$3,130 total

includes taxes & fees

22 Aug - 23 Aug

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Top Siena Hotel Reviews

Hotel Chiusarelli

8/10 Good

"The hotel itself was very nice. The staff were super helpful and we enjoyed our time. The AC and wifi were both a little weak, but otherwise, it was a pleasant stay. The breakfast buffet was also very good with a large selection."

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."

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