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 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Siena vacation homes

Spa

1. 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
Aug 29 - Aug 30
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Property grounds

2. 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 $241
CA $298 total
includes taxes & fees
Aug 23 - Aug 24
Cozy Tuscan-style apartment Suitable for families. Pets allowed
Outdoor dining

3. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is CA $515
CA $578 total
includes taxes & fees
Aug 31 - Sep 1
The Arch Among the Hills of Castellina
Outdoor dining

4. 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 14 - Sep 15
Peaceful corner with garden between Chianti and Crete, very close to Old Town
Exterior

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

Vana Hills House - Three Bedroom House, Sleeps 8
Monteriggioni
The price is CA $148
CA $397 total
includes taxes & fees
Aug 25 - Aug 26
Vana Hills House - Three Bedroom House, Sleeps 8
Property grounds

6. Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (81 reviews)
"It was a little tricky finding the villa but worth it. Better instructions would be helpful. The home was lovely. The gardens wonderful. A great respite fromThe city."
United States
Julie H.
The price is CA $193
CA $222 total
includes taxes & fees
Sep 1 - Sep 2
Villa with large garden in the Chianti hills
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 $493
CA $596 total
includes taxes & fees
Aug 21 - Aug 22
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, (9 reviews)
"Loved it!"
United States
Ryan C.
The price is CA $155
CA $252 total
includes taxes & fees
Aug 26 - Aug 27
Exclusive Stone Tower.
Pool

9. 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 $274
CA $497 total
includes taxes & fees
Sep 4 - Sep 5
House with pool for 4 pax
Outdoor dining

10. 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 $195 total
includes taxes & fees
Aug 24 - Aug 25
Detached house with garden a few minutes from the abbey of San Galgano
Outdoor dining

11. 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 23 - Aug 24
Casa Crevole di Martina in the Heart of Tuscany
Exterior detail

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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.4 out of 10, Exceptional, (23 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 $255 total
includes taxes & fees
Aug 21 - Aug 22
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Living area

13. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $348
CA $434 total
includes taxes & fees
Aug 31 - Sep 1
Casa Marisa in Castellina in Chianti
Pool

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

Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
Rosennano
The price is CA $403
CA $409 total
includes taxes & fees
Aug 25 - Aug 26
Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
Interior

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 $370
CA $586 total
includes taxes & fees
Sep 12 - Sep 13
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
Pool

16. 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 $652
CA $807 total
includes taxes & fees
Sep 1 - Sep 2
Farmhouse in Chianti
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 $209
CA $214 total
includes taxes & fees
Sep 14 - Sep 15
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Pool

18. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is CA $181
CA $207 total
includes taxes & fees
Aug 28 - Aug 29
Casa Vacanze Le Case
Interior

19. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is CA $181
CA $270 total
includes taxes & fees
Aug 24 - Aug 25
Chianti Craft House Badia a Passignano
Pool

20. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is CA $241
CA $550 total
includes taxes & fees
Aug 21 - Aug 22
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"
Tyler 1-night trip
Posted 2 days ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Siena

Siena Vacation Homes information

Number of reviews
16
Accommodation
129 Vacation Homes
Lowest Price
CA $222
Highest Price
CA $543

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