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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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

Deluxe Apartment | Premium bedding, down comforters, in-room safe, desk

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
Outdoor dining

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)
"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
Premium Apartment, 2 Bedrooms, 2 Bathrooms, Annex Building | Lanai

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
Property grounds

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
Outdoor pool

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
Property grounds

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
Property grounds

7. 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
Outdoor dining

8. 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
Interior

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
Outdoor pool

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, (33 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!!!
Exterior

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.
3 bedrooms, in-room safe, desk, iron/ironing board

12. 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
Property grounds

13. 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
Flat-screen TV, fireplace, table tennis

14. 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
Front of property

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
Outdoor pool

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
Outdoor dining

17. 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.
Interior

18. 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
Interior

19. 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
Terrace/patio

20. Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
Monteriggioni
10.0 out of 10, Exceptional, (16 reviews)
"Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really...
United States
Daniel D.
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
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

Hotel Athena

Hotel Athena

10/10 Excellent
"Excellent location with free. And easy parking. Great breakfast, extremely kind and helpful staff, small but adequate shower. Would definitely stay here in the future!!"
Lynne 3-night trip
Posted 6 hours ago
Hotel Athena

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