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

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

Toscana

CA $263 total

includes taxes & fees

Aug 29 - Aug 30

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.

CA $297 total

includes taxes & fees

Aug 28 - Aug 29

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

3. The Arch Among the Hills of Castellina

Topina

CA $528 total

includes taxes & fees

Sep 7 - Sep 8

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

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

Casetta

CA $171 total

includes taxes & fees

Sep 20 - Sep 21

A stone building with a tiled roof, a central door, and a small courtyard with a fountain.

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

Monteriggioni

CA $380 total

includes taxes & fees

Aug 31 - Sep 1

A well-lit garden at night with a large moon in the sky, various potted plants, and a neatly trimmed lawn.

6. Villa with large garden in the Chianti hills

Siena

Julie H.

CA $239 total

includes taxes & fees

Sep 7 - Sep 8

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 $598 total

includes taxes & fees

Aug 28 - Aug 29

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

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

Toscana

Julie M.

CA $195 total

includes taxes & fees

Aug 27 - Aug 28

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

9. Exclusive Stone Tower.

Casciano

Ryan C.

CA $247 total

includes taxes & fees

Sep 25 - Sep 26

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.

10. 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 $430 total

includes taxes & fees

Aug 28 - Aug 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 $256 total

includes taxes & fees

Aug 28 - Aug 29

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and greenery.

12. House with pool for 4 pax

Casole d'Elsa

Oliver E.

CA $480 total

includes taxes & fees

Sep 21 - Sep 22

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

13. Casa Vacanze Le Case

San Gimignano

Jackie

CA $204 total

includes taxes & fees

Aug 28 - Aug 29

A dining area with a table set for four, a large window with an arched ceiling, and a view of the outdoors.

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

casole d'elsa siena

Linda T.

CA $591 total

includes taxes & fees

Sep 12 - Sep 13

A street with outdoor seating, a building with a shop entrance, and a sign with a prohibition symbol.

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

Buonconvento

CA $194 total

includes taxes & fees

Aug 31 - Sep 1

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

16. Holday at Poggettone

Monteroni d'Arbia

CA $472 total

includes taxes & fees

Sep 22 - Sep 23

A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

17. Agritourism in val d'orcia

montalcino

CA $552 total

includes taxes & fees

Aug 27 - Aug 28

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

Radicondoli

CA $325 total

includes taxes & fees

Aug 28 - Aug 29

A spacious living room with leather sofas, a fireplace, and a kitchen in the background.

19. Casa Marisa in Castellina in Chianti

Castellina in Chianti

CA $436 total

includes taxes & fees

Aug 31 - Sep 1

A clear blue pool with a view of green hills and a distant building.

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

Rosennano

CA $395 total

includes taxes & fees

Aug 31 - Sep 1

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Top Siena Hotel Reviews

Hotel Chiusarelli

10/10 Excellent

"Perfectly clean, not the biggest room but worked for our one night stay. The staff were lovely and the location was perfect. Would stay again."

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."

Find out more about Siena

Siena Vacation Homes information

Number of reviews	177
Accommodation	129 Vacation Homes
Lowest Price	CA $171
Highest Price	CA $598

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Siena vacation 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. Peaceful corner with garden between Chianti and Crete, very close to Old Town

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

6. Villa with large garden in the Chianti hills

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