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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (91 reviews)
"Amazing staff, clean room, amazing pool!"
United States
Blake
Borgo Argiano
A swimming pool with a covered seating area and stone walls.

2. 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, (134 reviews)
"The property and it's facilities are more than ample for a family or group of friends wanting the space to relax in the amazing tuscan countryside with easy access to many wonderful towns. A car is required to really get the full benefit of the property. The pool and hot tub were both well used."
United States
Alastair B.
Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome
A swimming pool with lounge chairs and a tiled deck.

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, (83 reviews)
"Property had a pool and a big yard, very relaxing."
United States
Justyna C.
Villa with large garden in the Chianti hills
A bedroom with a bed, window, and a view of the outdoors. There is a bathroom with a sink and mirror.

5. Detached villa with a private pool and garden

Detached villa with a private pool and garden
Castellina in Chianti
9.0 out of 10, Wonderful, (31 reviews)
"Lovely little house. This was our second year staying and it did not disappoint. The extra bonus is the 5 minute walk into Castellina. One of our favourites."
United States
Catherine M.
Detached villa with a private pool and garden
An outdoor dining area with a long wooden table set for four, surrounded by stone walls and a stone bench.

6. 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, (26 reviews)
"Stunningly beautiful place to stay surrounded by hills and vineyards. Short drive to great restaurants or grocery stores. The host is thoughtful and accommodating. We loved our stay here "
United States
Aubrey S.
La Capanna - Radda in Chianti. Newly renovated stone farmhouse with pool & A/C
A stone arch window with a view of a rural landscape, including fields and a tree with red flowers.

7. Beautiful house on Chianti hilltop with exceptional views.

Beautiful house on Chianti hilltop with exceptional views.
Siena
10.0 out of 10, Exceptional, (79 reviews)
"House was clean and comfortable and the place was even better than the pictures online. Stunning views and a great location to explore the many beautiful towns in the area. "
United States
Darren S.
Beautiful house on Chianti hilltop with exceptional views.
A balcony with a view of a green landscape, including hills and a tall tree.

8. 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 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 house with a wooden door and shutters, surrounded by potted plants and a stone pathway.

10. Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire
Castellina in Chianti
10.0 out of 10, Exceptional, (159 reviews)
"A charming farmhouse with a beautiful view. The hosts were extremely accommodating, especially when our car rental was inoperative. Excellent communication!"
United States
Annie L.
Farmhouse in the heart of the real chiantishire
An outdoor patio with a wooden table and chairs, a hanging light fixture, and a view of a valley.

11. Private villa with swimming pool and spectacular views of Siena

Private villa with swimming pool and spectacular views of Siena
Casetta
9.6 out of 10, Exceptional, (69 reviews)
"Beautiful area and spacious house. Very enjoyable stay."
United States
Philip G.
Private villa with swimming pool and spectacular views of Siena
A stone building with a swimming pool, surrounded by trees and a clear blue sky.

12. 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, (35 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.

13. 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, (27 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 rustic room with a stone wall, a fireplace, a white sofa, and a wooden bench.

14. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (78 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is AED 619
AED 841 total
includes taxes & fees
2 Nov - 3 Nov
The House of Alice, charm and relaxation
A pool area with lounge chairs, a clear blue pool, and a garden with daisies.

15. House with private pool with beautiful view Val d 'Orcia

House with private pool with beautiful view Val d 'Orcia
Monticchiello
9.8 out of 10, Exceptional, (50 reviews)
"Fantastic location, quiet house."
Canada
Nik V.
House with private pool with beautiful view Val d 'Orcia
A large, historic building with multiple floors and a courtyard, surrounded by lush greenery and rolling hills.

16. Borgo Villa Certano

Borgo Villa Certano
Siena
10.0 out of 10, Exceptional, (1 review)
"Absolutely beautiful setting out in the hills of Siena. Our apartment was clean and functional. It really needed some easy comfortable chairs to sit in. There was definitely room in the apartment."
United States
Angela
Borgo Villa Certano
A swimming pool with clear blue water, surrounded by lush greenery and a view of distant hills.

17. Casale di Villore

Casale di Villore
Poggibonsi
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic property. Can’t wait to return next year. "
Canada
Owen
Casale di Villore
A wooden barrel structure with an open door, situated on a wooden deck surrounded by lavender fields and olive trees.

18. Magnificent farmhouse in Val d'Orcia with a private pool and sauna

Magnificent farmhouse in Val d'Orcia with a private pool and sauna
Radicofani
10.0 out of 10, Exceptional, (14 reviews)
"We enjoyed a relaxing time at you house. Close to a lot of nearby activities. "
United States
Michael B.
Magnificent farmhouse in Val d'Orcia with a private pool and sauna
A stone building with multiple windows and a chimney.

19. 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 AED 472
AED 536 total
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
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.

20. 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
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

8/10 Good
"When we arrived the gate to the hotel was locked. Called the hotel and then a person drove up and helped us to check in. He was very nice. The hotel is very old, but a decent place to stay for a night."
John 1-night trip
Posted 5 hours ago
Nuovo Etruria Resort

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