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

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.

HK$1,358 total

includes taxes & fees

25 Oct - 26 Oct

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.

HK$1,645 total

includes taxes & fees

21 Oct - 22 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

HK$1,549 total

includes taxes & fees

3 Nov - 4 Nov

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

4. The Arch Among the Hills of Castellina

Topina

HK$2,455 total

includes taxes & fees

8 Nov - 9 Nov

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

5. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$73,955 total

includes taxes & fees

27 Oct - 28 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

HK$862 total

includes taxes & fees

9 Nov - 10 Nov

A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

7. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

Monteroni d'Arbia

HK$1,038 total

includes taxes & fees

25 Oct - 26 Oct

A stone building with multiple windows and a chimney.

8. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

HK$1,143 total

includes taxes & fees

16 Nov - 17 Nov

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

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

HK$1,400 total

includes taxes & fees

21 Oct - 22 Oct

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

10. Casa Vacanze Le Case

San Gimignano

Andrew

HK$840 total

includes taxes & fees

2 Nov - 3 Nov

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

11. Exclusive Stone Tower.

Casciano

Ryan C.

HK$1,233 total

includes taxes & fees

22 Oct - 23 Oct

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

12. Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi

Castelnuovo Berardenga

Anonymous traveller

HK$5,702 total

includes taxes & fees

3 Nov - 4 Nov

A bedroom with a bed, a dresser, a red cabinet, a window, and a chair.

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

Radicondoli

HK$1,247 total

includes taxes & fees

19 Nov - 20 Nov

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.

14. 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."