Siena Vacation Home Rentals from CA $152: 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 brick building with a sliding glass door entrance, a large potted plant, and two smaller potted plants outside.

1. GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

Siena

CA $289 total

includes taxes & fees

Oct 18 - Oct 19

A stone building with a sign reading "VIA DI CALZOLERIA".

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

Siena City Centre

Louise B.

CA $274 total

includes taxes & fees

Oct 7 - Oct 8

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 $294 total

includes taxes & fees

Oct 7 - Oct 8

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

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

Toscana

CA $277 total

includes taxes & fees

Oct 8 - Oct 9

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

5. The Arch Among the Hills of Castellina

Topina

CA $446 total

includes taxes & fees

Nov 2 - Nov 3

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

6. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

CA $13,449 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.

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

Casetta

CA $157 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.

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

Monteroni d'Arbia

CA $189 total

includes taxes & fees

Nov 1 - Nov 2

A stone building with multiple windows and a chimney.

9. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

CA $218 total

includes taxes & fees

Nov 3 - Nov 4

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

10. Casa Vacanze Le Case

San Gimignano

Andrew

CA $152 total

includes taxes & fees

Nov 2 - Nov 3

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 $254 total

includes taxes & fees

Oct 9 - Oct 10

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

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

Castelnuovo Berardenga

Anonymous traveller

CA $585 total

includes taxes & fees

Oct 12 - Oct 13

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

13. Exclusive Stone Tower.

Casciano

Ryan C.

CA $224 total

includes taxes & fees

Oct 7 - Oct 8

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

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

Radicondoli

CA $227 total

includes taxes & fees

Nov 1 - Nov 2

A glass on a wooden table with a pool and a building in the background.

15. Apartment in Chianti With Pool ID 513

Casole d'Elsa

CA $403 total

includes taxes & fees

Oct 7 - Oct 8

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.

16. 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 $408 total

includes taxes & fees

Oct 11 - Oct 12

A bedroom with a stone wall, a bed, a bookshelf, and a hanging light fixture.

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

Poggiobrucoli

CA $405 total

includes taxes & fees

Nov 2 - Nov 3

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

18. House with pool for 4 pax

Pievescola

Oliver E.

CA $444 total

includes taxes & fees

Oct 7 - Oct 8

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

19. 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 $760 total

includes taxes & fees

Oct 13 - Oct 14

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

20. Casa Marisa in Castellina in Chianti

Castellina in Chianti

CA $432 total

includes taxes & fees

Oct 11 - Oct 12

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Top Siena Hotel Reviews

Hotel Executive

10/10 Excellent

"Nice modern business hotel with spacious rooms. Mine had a balcony too. Plenty of parking on site. I ate in the restaurant which was good and reasonably priced. It’s a bit out of the way, so definitely not somewhere to explore Siena on foot by!"

Piccolo Hotel Etruria

10/10 Excellent

"Great location near the plaza and many stores/restaurants. Everything works except for in room safe. No electric kettle even though I requested it. Good grocery store and coffee shop only steps away. Located in historic area and building. Big triple room and quiet setting and nice lounge on second floor. AC works well. I recommend this place and will stay there again. Richard from Canada."

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"This hotel was PERFECT for our honeymoon trip to Siena. It was peaceful and quiet, but still close enough to get to the city centre and the train station easily. The pool was a perfect oasis after hot days. The staff were so friendly and helpful. The terrace was a gorgeous place for a night cap at the end of the night. We would definitely stay here again."

Hotel Certosa Di Maggiano

10/10 Excellent

"Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc. The property was beautiful, maintained nicely, and was very quiet. Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!"

Find out more about Siena

Siena Vacation Homes information

Number of reviews	70
Accommodation	132 Vacation Homes
Lowest Price	CA $152
Highest Price	CA $13,449

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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. GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

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

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

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

5. The Arch Among the Hills of Castellina

6. Ebbio – Villa and Organic Farm in Monteriggioni

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