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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Siena vacation homes

Exterior detail

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
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
Spa

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

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is CA $145
CA $262 total
includes taxes & fees
Sep 6 - Sep 7
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Property grounds

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 $240
CA $297 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Tuscan-style apartment Suitable for families. Pets allowed
Outdoor dining

4. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is CA $417
CA $479 total
includes taxes & fees
Oct 1 - Oct 2
The Arch Among the Hills of Castellina
Outdoor dining

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 $128
CA $170 total
includes taxes & fees
Sep 28 - Sep 29
Peaceful corner with garden between Chianti and Crete, very close to Old Town
Exterior

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

Vana Hills House - Three Bedroom House, Sleeps 8
Monteriggioni
The price is CA $138
CA $387 total
includes taxes & fees
Sep 7 - Sep 8
Vana Hills House - Three Bedroom House, Sleeps 8
Pool

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 $491
CA $593 total
includes taxes & fees
Sep 11 - Sep 12
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Exterior detail

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 $136
CA $232 total
includes taxes & fees
Sep 30 - Oct 1
Exclusive Stone Tower.
Outdoor dining

9. 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 $387
CA $426 total
includes taxes & fees
Sep 11 - Sep 12
Casa Crevole di Martina in the Heart of Tuscany
Pool

10. 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 $240
CA $462 total
includes taxes & fees
Oct 1 - Oct 2
House with pool for 4 pax
Exterior detail

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 $129
CA $256 total
includes taxes & fees
Sep 14 - Sep 15
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Property grounds

12. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $346
CA $433 total
includes taxes & fees
Sep 8 - Sep 9
Casa Marisa in Castellina in Chianti
Outdoor dining

13. 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 $80
CA $194 total
includes taxes & fees
Sep 16 - Sep 17
Detached house with garden a few minutes from the abbey of San Galgano
Interior

14. 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 $370
CA $588 total
includes taxes & fees
Sep 12 - Sep 13
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
Pool

15. 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 $175
CA $200 total
includes taxes & fees
Sep 17 - Sep 18
Casa Vacanze Le Case
Interior

16. 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 $181
CA $268 total
includes taxes & fees
Sep 6 - Sep 7
Chianti Craft House Badia a Passignano
Exterior

17. 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 $208
CA $213 total
includes taxes & fees
Sep 23 - Sep 24
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Interior

18. THE CASINA OF SANT 'AGOSTINO

THE CASINA OF SANT 'AGOSTINO
Colle di Val d'Elsa
The price is CA $192
CA $244 total
includes taxes & fees
Sep 8 - Sep 9
THE CASINA OF SANT 'AGOSTINO
Pool

19. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...
United States
Lara W.
The price is CA $649
CA $804 total
includes taxes & fees
Sep 14 - Sep 15
Farmhouse in Chianti
Pool

20. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is CA $240
CA $550 total
includes taxes & fees
Sep 9 - Sep 10
Agritourism in val d'orcia
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

Hotel Santa Caterina

Hotel Santa Caterina

10/10 Excellent
"Great location just outside the limited traffic zone, and available parking. Staff were very accommodating and friendly. Fantastic breakfast spread with a lovely view of the Tuscan hills. The room was on the smaller side, but more than adequate for one person for a short stay. The a/c worked very well!"
Gaurav 1-night trip
Posted 23 hours ago
Hotel Santa Caterina

Find out more about Siena

Siena Vacation Homes information

Number of reviews
115
Accommodation
129 Vacation Homes
Lowest Price
CA $170
Highest Price
CA $804

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