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

Siena Vacation Rentals

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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

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 $169
CA $318 total
includes taxes & fees
Sep 23 - Sep 24
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. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is CA $145
CA $263 total
includes taxes & fees
Sep 6 - Sep 7
Love Nest Siena: Romantic Suite with SPA & Jacuzzi

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 $242
CA $296 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Tuscan-style apartment Suitable for families. Pets allowed

4. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is CA $464
CA $527 total
includes taxes & fees
Sep 6 - Sep 7
The Arch Among the Hills of Castellina

5. 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 $129
CA $171 total
includes taxes & fees
Sep 20 - Sep 21
Peaceful corner with garden between Chianti and Crete, very close to Old Town

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

Vana Hills House - Three Bedroom House, Sleeps 8
Monteriggioni
The price is CA $130
CA $379 total
includes taxes & fees
Sep 2 - Sep 3
Vana Hills House - Three Bedroom House, Sleeps 8

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

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (1 review)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveller
The price is CA $493
CA $596 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

8. 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 $143
CA $240 total
includes taxes & fees
Sep 21 - Sep 22
Exclusive Stone Tower.

9. 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 $81
CA $195 total
includes taxes & fees
Aug 31 - Sep 1
Detached house with garden a few minutes from the abbey of San Galgano

10. 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 $389
CA $428 total
includes taxes & fees
Aug 31 - Sep 1
Casa Crevole di Martina in the Heart of Tuscany

11. 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, (24 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 $130
CA $257 total
includes taxes & fees
Aug 31 - Sep 1
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

12. House with pool for 4 pax

House with pool for 4 pax
Casole d'Elsa
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 $258
CA $477 total
includes taxes & fees
Sep 23 - Sep 24
House with pool for 4 pax

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

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Buonconvento
The price is CA $209
CA $214 total
includes taxes & fees
Sep 14 - Sep 15
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

14. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is CA $179
CA $205 total
includes taxes & fees
Sep 17 - Sep 18
Casa Vacanze Le Case

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

La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
casole d'elsa siena
10.0 out of 10, Exceptional, (43 reviews)
"We stayed in this beautiful clean, fully airconditioned apartment for 12 days, perfect location for trips to the surrounding area like Siena, Florence, Monteriggioni, Volterra & San Gimignano. The apartment is situated in a peaceful Agriturismo with lots of privacy and a great swimming pool. The owners are really hospitable and you feel welcome right away. Highly recommendable."
Netherlands
Linda T.
The price is CA $371
CA $588 total
includes taxes & fees
Sep 12 - Sep 13
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

16. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $348
CA $435 total
includes taxes & fees
Aug 31 - Sep 1
Casa Marisa in Castellina in Chianti

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

Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
Rosennano
The price is CA $387
CA $394 total
includes taxes & fees
Aug 31 - Sep 1
Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

18. 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 $274
CA $274 total
includes taxes & fees
Aug 31 - Sep 1
A Nest with a View - A Romantic Retreat Within the City Walls

19. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is CA $242
CA $551 total
includes taxes & fees
Aug 31 - Sep 1
Agritourism in val d'orcia

20. THE CASINA OF SANT 'AGOSTINO

THE CASINA OF SANT 'AGOSTINO
Colle di Val d'Elsa
The price is CA $193
CA $245 total
includes taxes & fees
Sep 4 - Sep 5
THE CASINA OF SANT 'AGOSTINO
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

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Siena Vacation Homes information

Number of reviews
97
Accommodation
129 Vacation Homes
Lowest Price
CA $171
Highest Price
CA $596

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