Siena Vacation Home Rentals from CA $171: Search Top Private Vacation Homes for Rent

A historic town with terracotta-roof buildings, a prominent church, and a hilltop fortress.

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Our top choices for Siena vacation 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.

CA $255 total

includes taxes & fees

Sep 29 - Sep 30

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

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

Toscana

CA $278 total

includes taxes & fees

Sep 27 - Sep 28

A rustic building with a brick facade, a small arched window, and a door.

3. 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.

CA $299 total

includes taxes & fees

Oct 2 - Oct 3

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

4. The Arch Among the Hills of Castellina

Topina

CA $481 total

includes taxes & fees

Oct 5 - Oct 6

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

5. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

CA $13,523 total

includes taxes & fees

Oct 8 - Oct 9

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

CA $171 total

includes taxes & fees

Sep 28 - Sep 29

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

CA $614 total

includes taxes & fees

Sep 27 - Sep 28

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

8. Exclusive Stone Tower.

Casciano

Ryan C.

CA $225 total

includes taxes & fees

Sep 24 - Sep 25

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.

9. 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.

CA $419 total

includes taxes & fees

Sep 30 - Oct 1

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.

CA $195 total

includes taxes & fees

Sep 28 - Sep 29

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

11. 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

CA $257 total

includes taxes & fees

Sep 29 - Sep 30

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.

CA $434 total

includes taxes & fees

Oct 3 - Oct 4

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

13. Casa Vacanze Le Case

San Gimignano

Jackie

CA $207 total

includes taxes & fees

Sep 25 - Sep 26

A brick building with a garden, a metal fence, and a clear sky.

14. Casa Marisa in Castellina in Chianti

Castellina in Chianti

CA $434 total

includes taxes & fees

Sep 29 - Sep 30

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

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

Radicondoli

CA $275 total

includes taxes & fees

Sep 24 - Sep 25

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.

CA $807 total

includes taxes & fees

Oct 5 - Oct 6

A two-story house with a stone foundation, wooden shutters, and a covered porch with outdoor furniture.

17. Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

Casole d'Elsa

"Pros: Das Haus ist liebevoll eingerichtet, hat zwei schöne Bäder und eine wunderbare schattige Terrasse, von der man ins Grüne schaut, tagsüber ab und zu die Schafe nebenan und abends die Wildschweine hören kann. Das Haus liegt sehr ruhig in einem abgeschiedenen Weiler. Es sind ausreichend Liegestühle vorhanden, um im Garten zu entspannen. Die Klimaanlage im Haus funktioniert bestens. Besonders hervorzuheben sind die sehr herzlichen und hilfsbereiten Vermieter, die auch in dem kleinen Ort wohnen...

Anonymous traveller

CA $834 total

includes taxes & fees

Oct 12 - Oct 13

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

18. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

CA $291 total

includes taxes & fees

Sep 24 - Sep 25

A table set outdoors with fruits, a pitcher of red drink, and a vase of flowers.

19. Holiday Home 'Rustico Con Jacuzzi In Toscana' with Shared Pool, Wi-Fi and Air Conditioning

Colle di Val d'Elsa

Anonymous traveller

CA $521 total

includes taxes & fees

Sep 24 - Sep 25

A small brick structure with an arched entrance, surrounded by gravel, potted plants, and trees.

20. Holday at Poggettone

Monteroni d'Arbia

CA $354 total

includes taxes & fees

Oct 5 - Oct 6

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Top Siena Hotel Reviews

Hotel Chiusarelli

8/10 Good

"This hotel is well maintained and delicious breakfast. Great location to walk to everything in Siena"

Piccolo Hotel Etruria

10/10 Excellent

"The hotel was very close to the plaza El Campo. The one night we ate in the plaza there was a celebration, which was wonderful to observe, while we were eating our dinner in a wonderful restaurant. Food was excellent service was excellent. The Central city of Siena was fun to experience with narrow passages and lots to see."

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good

"Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty."

Find out more about Siena

Siena Vacation Homes information

Number of reviews	80
Accommodation	132 Vacation Homes
Lowest Price	CA $171
Highest Price	CA $13,523

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Siena vacation homes

1. THE TOLOMEI - apartment in the heart of the main street

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

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

4. The Arch Among the Hills of Castellina

5. Ebbio – Villa and Organic Farm in Monteriggioni

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