Siena Vacation Home Rentals from CA $145: 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 rustic building with a brick facade, a small arched window, and a door.

1. 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 $295 total

includes taxes & fees

Oct 16 - Oct 17

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 $279 total

includes taxes & fees

Oct 20 - Oct 21

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

3. The Arch Among the Hills of Castellina

Topina

CA $445 total

includes taxes & fees

Nov 2 - Nov 3

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

4. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

CA $13,394 total

includes taxes & fees

Oct 28 - Oct 29

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

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

Casetta

CA $156 total

includes taxes & fees

Nov 2 - Nov 3

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

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

Monteroni d'Arbia

CA $188 total

includes taxes & fees

Oct 15 - Oct 16

A stone building with multiple windows and a chimney.

7. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

CA $207 total

includes taxes & fees

Nov 8 - Nov 9

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

8. Casa Vacanze Le Case

San Gimignano

Andrew

CA $145 total

includes taxes & fees

Nov 5 - Nov 6

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

CA $255 total

includes taxes & fees

Oct 14 - Oct 15

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

10. Exclusive Stone Tower.

Casciano

Ryan C.

CA $223 total

includes taxes & fees

Oct 14 - Oct 15

A balcony with potted plants and a view of rolling hills and mountains.

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

Radicondoli

CA $227 total

includes taxes & fees

Nov 1 - Nov 2

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 $456 total

includes taxes & fees

Oct 22 - Oct 23

A bedroom with a bed, a dresser, a chair, a window, and a view of the outside.

13. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

Poggiobrucoli

CA $403 total

includes taxes & fees

Nov 2 - Nov 3

A stone bench with a rustic fire pit in a garden setting.

14. Apartment in Chianti With Pool ID 513

Casole d'Elsa

CA $448 total

includes taxes & fees

Oct 22 - Oct 23

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.

15. 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 $406 total

includes taxes & fees

Oct 14 - Oct 15

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

16. 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 $757 total

includes taxes & fees

Oct 19 - Oct 20

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

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

Castelnuovo Berardenga

Anonymous traveller

CA $1,033 total

includes taxes & fees

Nov 2 - Nov 3

A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

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

Toscana

Julie M.

CA $193 total

includes taxes & fees

Oct 14 - Oct 15

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

19. Casa Marisa in Castellina in Chianti

Castellina in Chianti

CA $430 total

includes taxes & fees

Oct 18 - Oct 19

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

20. Holday at Poggettone

Monteroni d'Arbia

CA $352 total

includes taxes & fees

Oct 14 - Oct 15

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Top Siena Hotel Reviews

Palazzo Ravizza

10/10 Excellent

"A beautiful palazzo turned hotel! So charming and lovely and extremely walkable to town. Room was huge and so comfortable. The property has a beautiful garden with a lovely view too. We absolutely loved our stay here- already planning our trip back!"

Hotel Athena

10/10 Excellent

"Reception staff very friendly and helpful. Room on top floor had two full length windows with spectacular views. Older property but updated nicely; not modern but comfortable. Comfy bed, linens and pillows. Nice breakfast with lots of variety. There are two floors that have breakfast - the lowest level is more spacious and had food replaced more quickly than upper level. Hotel seems far, but everything is 5 to 15 minutes away. We found our favorite wine spot just a 5 minute walk away at Tuscan Wine School. But do go to the rooftop terrace for lovely views."

Il Chiostro del Carmine

10/10 Excellent

"Great breakfast, stunning views of the Tuscan countryside and felt like walking into the past. Exactly as per the photos, a wonderful ambience, full of charm and character. Well located on the edge of the old town, less than 10 minutes walk to the centre. The staff were so friendly and helpful. I would not hesitate to recommend this hotel and hope to come back myself."

Find out more about Siena

Siena Vacation Homes information

Number of reviews	54
Accommodation	132 Vacation Homes
Lowest Price	CA $145
Highest Price	CA $13,394

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

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

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