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

Siena Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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

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
The price is CA $101
CA $233 total
includes taxes & fees
Oct 18 - Oct 19
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
A stone building with a sign reading "VIA DI CALZOLERIA".

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

THE TOLOMEI - apartment in the heart of the main street
Siena City Centre
8.4 out of 10, Very good, (5 reviews)
"I stayed for a month and found the apartment ti be very comfortable and si convenient for all that Siena has to offer."
United States
Louise B.
The price is CA $145
CA $245 total
includes taxes & fees
Oct 18 - Oct 19
THE TOLOMEI - apartment in the heart of the main street
A rustic building with a brick facade, a small arched window, and a door.

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

Cozy Tuscan-style apartment Suitable for families. Pets allowed
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"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."
United States
Shanti R.
The price is CA $238
CA $296 total
includes taxes & fees
Oct 24 - Oct 25
Cozy Tuscan-style apartment Suitable for families. Pets allowed
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

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is CA $157
CA $277 total
includes taxes & fees
Oct 24 - Oct 25
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
A stone building with a gravel path, outdoor seating, and greenery.

5. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is CA $382
CA $444 total
includes taxes & fees
Nov 2 - Nov 3
The Arch Among the Hills of Castellina
A rustic villa with a garden, a pond, and a mountainous backdrop.

6. Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is CA $13,350
CA $13,358 total
includes taxes & fees
Oct 27 - Oct 28
Ebbio – Villa and Organic Farm in Monteriggioni
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

Peaceful corner with garden between Chianti and Crete, very close to Old Town
Casetta
The price is CA $114
CA $156 total
includes taxes & fees
Nov 16 - Nov 17
Peaceful corner with garden between Chianti and Crete, very close to Old Town
A stone building with multiple windows and a chimney.

8. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is CA $182
CA $206 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

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

Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
Monteroni d'Arbia
The price is CA $151
CA $188 total
includes taxes & fees
Oct 31 - Nov 1
Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

10. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is CA $121
CA $141 total
includes taxes & fees
Nov 5 - Nov 6
Casa Vacanze Le Case
A stone building with two windows, one with green shutters, and a rose bush in the foreground.

11. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is CA $127
CA $223 total
includes taxes & fees
Oct 23 - Oct 24
Exclusive Stone Tower.
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

12. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (27 reviews)
"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...
Canada
James
The price is CA $129
CA $254 total
includes taxes & fees
Oct 19 - Oct 20
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A balcony with potted plants and a view of rolling hills and mountains.

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

A Nest with a View - A Romantic Retreat Within the City Walls
Radicondoli
The price is CA $227
CA $227 total
includes taxes & fees
Nov 8 - Nov 9
A Nest with a View - A Romantic Retreat Within the City Walls
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

Casa Crevole di Martina in the Heart of Tuscany
Murlo
10.0 out of 10, Exceptional, (1 review)
"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."
Germany
Sybille F.
The price is CA $366
CA $405 total
includes taxes & fees
Oct 18 - Oct 19
Casa Crevole di Martina in the Heart of Tuscany
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and greenery.

15. House with pool for 4 pax

House with pool for 4 pax
Pievescola
9.4 out of 10, Exceptional, (3 reviews)
"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"
Germany
Oliver E.
The price is CA $226
CA $444 total
includes taxes & fees
Oct 24 - Oct 25
House with pool for 4 pax
A stone bench with a rustic fire pit in a garden setting.

16. Apartment in Chianti With Pool ID 513

Apartment in Chianti With Pool ID 513
Casole d'Elsa
The price is CA $404
CA $447 total
includes taxes & fees
Oct 26 - Oct 27
Apartment in Chianti With Pool ID 513
A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

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

Detached house with garden a few minutes from the abbey of San Galgano
Toscana
10.0 out of 10, Exceptional, (1 review)
"Petite maison cosy et juste parfaite pour deux personnes. La localisation est très bonne, à l’entrée du village de Monticiano. L’accueil a été enthousiaste et la communication très fluide. Merci pour ce beau séjour ! On recommande !"
United States
Julie M.
The price is CA $79
CA $192 total
includes taxes & fees
Oct 24 - Oct 25
Detached house with garden a few minutes from the abbey of San Galgano
A brick building with a garden, a metal fence, and a clear sky.

18. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $344
CA $430 total
includes taxes & fees
Oct 18 - Oct 19
Casa Marisa in Castellina in Chianti
A rectangular swimming pool with a wooden deck and metal railings, surrounded by a grassy area with trees and a clear sky.

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

Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi
Castelnuovo Berardenga
8.0 out of 10, Very good, (1 review)
"Pros: Posto meraviglioso. Bellissima location e bellissimo panorama Cons: Un po' più di cura e pulizia nella zona piscina. Jacuzzi chiusa e pensavamo di trovarla aperta"
Italy
Anonymous traveller
The price is CA $1,023
CA $1,030 total
includes taxes & fees
Nov 3 - Nov 4
Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi
A view through a wooden door of a courtyard with stone walls and potted plants.

20. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is CA $199
CA $292 total
includes taxes & fees
Oct 28 - Oct 29
Chianti Craft House Badia a Passignano
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Siena Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"We had the most amazing stay in this beautiful hotel. Our room was so charming, and the entire hotel felt warm and welcoming in the most Italian way. Breakfast each morning included a beautiful spread of savory and sweet, and croissants that were better than Paris. The terrace sunsets looking over Siena welcomed us each evening after a long day of walking. Location was top notch. Our only “complaint” was that the bed was VERY firm. We will be back!!"
susan 7-night trip
Posted 7 hours ago
Palazzo Ravizza

Find out more about Siena

Siena Vacation Homes information

Number of reviews
71
Accommodation
132 Vacation Homes
Lowest Price
CA $141
Highest Price
CA $13,358

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