A historic town with a prominent tower and a rainbow arching over it.

Vacation Homes in Province of Siena

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Top Cities in Province of Siena

A historic square with a prominent tower and statues.
Vacation HomesVacation Homes

Pienza

Pienza

Our top choices for Province of Siena vacation homes

A bedroom with a large bed, a wooden ceiling, and a brick archway.

1. Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (88 reviews)
"Amazing staff, clean room, amazing pool!"
United States
Blake
Borgo Argiano
An outdoor dining area with a long wooden table set for four, surrounded by stone walls and a stone bench.

2. La Capanna - Radda in Chianti. Newly renovated stone farmhouse with pool & A/C

La Capanna - Radda in Chianti. Newly renovated stone farmhouse with pool & A/C
Radda in Chianti
10.0 out of 10, Exceptional, (24 reviews)
La Capanna - Radda in Chianti. Newly renovated stone farmhouse with pool & A/C
A table set outdoors with food, wine, and a view of a countryside landscape.

3. Il Palazzetto

Il Palazzetto
Siena
9.6 out of 10, Exceptional, (7 reviews)
"Endroit agréable, idéal pour visiter Sienne à moins de 10mns en voiture et rayonner dans la région."
France
Francois
Il Palazzetto
A well-lit garden at night with a large moon in the sky, various potted plants, and a neatly trimmed lawn.

4. Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (82 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.
Villa with large garden in the Chianti hills
A swimming pool with a covered seating area and stone walls.

5. Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome
Cetona
10.0 out of 10, Exceptional, (130 reviews)
"We had a wonderful stay at this amazing villa close to Montepulciano, Montalcino and Pienza! The villa was beautiful inside, including 4 large bedrooms with very comfortable beds, a spacious kitchen and dining area, and a very relaxing living area. The outside of the villa was amazing with a gorgeous view of the countryside from the backyard pool as well as a separate building for the hot tub! Our host Valario was very accessible and helpful throughout the check in process as well as during...
United States
Diane K.
Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome
A balcony with a view of a green landscape, including hills and a tall tree.

6. Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi

Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi
Radicondoli
9.4 out of 10, Exceptional, (42 reviews)
"absolutely stunning place to relax, enjoy the view on the terrace/balcony, and explore tuscany! a handful of amazing spots to eat in the town itself"
United States
MARK P.
Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi
A table set with food and drinks, a vase with flowers, and a view of a green landscape.

7. INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Montepulciano
9.6 out of 10, Exceptional, (90 reviews)
"Loved this property. Right at the edge of town. Beautiful views"
United States
Celya F.
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
A stone building with a wooden door and arched windows, surrounded by a well-maintained garden with flowering plants.

8. Independent house in the hills of the Sienese countryside

Independent house in the hills of the Sienese countryside
Siena
10.0 out of 10, Exceptional, (84 reviews)
"Wonderful hosts. Lovely location. "
Australia
Michael C.
Independent house in the hills of the Sienese countryside
A view through a window with a rural landscape, including fields and a small building with a tiled roof.

9. Sweet home, the home of the small village

Sweet home, the home of the small village
Colle di Val d'Elsa
9.4 out of 10, Exceptional, (13 reviews)
"It is a lovely place to stay and discover Tuscany. The house is clean, big and the pool is great to have a refeshing dive. We enjoyed our stay a lot."
United States
Djip d.
Sweet home, the home of the small village
A stone building with a swimming pool, surrounded by trees and a clear blue sky.

10. Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!
Sarteano
10.0 out of 10, Exceptional, (34 reviews)
"The house was very clean and comfortable. The showers are a bit small and the road to the house is a little challenging but overall we enjoyed our stay. The key holders re wonderful people and left us surprises almost daily. It included bottles of wine, pastries and groceries. They stocked the house with bottles of water, laundry detergent, trash bags, basically all our needs. I would highly recommend a stay at this villa."
United States
Michael W.
Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!
A stone house with a covered patio, potted plants, and a grassy yard.

11. Villa Banditello, secluded, panoramic view over Montepulciano valley.

Villa Banditello, secluded, panoramic view over Montepulciano valley.
torrita di siena, fraz. montefollonico
10.0 out of 10, Exceptional, (26 reviews)
"Just amazing. From views of the countryside, to the peaceful surroundings, this home is a one of a kind. We absolutely loved our stay. Highly recommend to ALL!! "
United States
Nicol A.
Villa Banditello, secluded, panoramic view over Montepulciano valley.
A stone building with a door, surrounded by a field of white flowers.

12. MONTEGONFOLI 4, Apartment for 4 adults with amazing views on San Gimignano

MONTEGONFOLI 4, Apartment for 4 adults with amazing views on San Gimignano
san gimignano
9.4 out of 10, Exceptional, (26 reviews)
"Beautiful views and quiet surroundings. "
United States
Barbara F.
MONTEGONFOLI 4, Apartment for 4 adults with amazing views on San Gimignano
A hallway leading to an outdoor patio with a table and chairs, framed artwork on the walls, and a rustic ceiling.

13. Casale di Villore

Casale di Villore
Poggibonsi
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic property. Can’t wait to return next year. "
Canada
Owen
Casale di Villore
An outdoor reading area with a book, a glass of water, and a glass of juice on a table under a tree, with a brick building in the background.

14. Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Siena
10.0 out of 10, Exceptional, (17 reviews)
"Very special Villa on the winery. Great host and will be coming back next time we are in Tuscany."
United States
Michael H.
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
A stone building with multiple windows and a chimney.

15. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
A swimming pool with a view of a hill and trees.

16. Beautiful Tuscan farmhouse with stunning views of Chianti countryside

Beautiful Tuscan farmhouse with stunning views of Chianti countryside
Castellina in Chianti
10.0 out of 10, Exceptional, (52 reviews)
"The house and grounds were absolutely wonderful! There is no place I'd rather stay in Tuscany."
United States
Jonathan S.
Beautiful Tuscan farmhouse with stunning views of Chianti countryside
A bedroom with a bed, window, and a view of the outdoors. There is a bathroom with a sink and mirror.

17. detached villa with private pool and garden

detached villa with private pool and garden
Castellina in Chianti
9.0 out of 10, Wonderful, (31 reviews)
"Brilliant location, very easy access to village. Fantastic pool and garden for relaxation both of a very high standard. Check in was easy, kitchen and interior facilities were adequate. "
United Kingdom
Elaine D.
detached villa with private pool and garden
A terrace with a table and chairs, overlooking a scenic landscape.

18. Villa Mulinello, secluded, panoramic view over Montepulciano valley.

Villa Mulinello, secluded, panoramic view over Montepulciano valley.
torrita di siena, fraz. montefollonico
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful villa overlooking the countryside. It’s off the main road and a little distance from town."
United States
Sean L.
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
A spacious living room with a high ceiling, ornate ceiling beams, a chandelier, and a view of a historic building outside.

19. Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Siena City Centre
10.0 out of 10, Exceptional, (25 reviews)
"Perfect location!"
United States
Brent F.
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
An open wooden door leading to a stone pathway with a metal gate.

20. Esclusivo per te

Esclusivo per te
COLLE VAL D' ELSA
9.8 out of 10, Exceptional, (16 reviews)
"Location is out in the country but an easy drive to Volterra, San Gimignano and beyond. Property is very well maintained and the hosts are lovely people."
United States
Norman K.
Esclusivo per te
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 Province of Siena Hotel Reviews

Nuovo Etruria Resort

Nuovo Etruria Resort

10/10 Excellent
"Great big room with excellent amenities. Wonderful staff."
Nasser 1-night trip
Posted 11 hours ago
Nuovo Etruria Resort

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