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
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

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, (86 reviews)
"Amazing staff, clean room, amazing pool!"
United States
Blake
Borgo Argiano
TV, fireplace, DVD player, table tennis

2. Idyllic guest house in Tuscan country house style with swimming pool

Idyllic guest house in Tuscan country house style with swimming pool
Sinalunga
10.0 out of 10, Exceptional, (28 reviews)
"A truly beautiful place. It's quiet and idyllic and feels just like living in Italy. You can spend the day going to places that might have tons of tourists and then come back here to a peaceful beautiful house."
United States
Dean B.
Idyllic guest house in Tuscan country house style with swimming pool
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
Outdoor pool

4. 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, (128 reviews)
"This property is AMAZING. The photos online do not do it justice. It is a Tuscan paradise and the house is truly a HOME. The kitchen is well appointed with every item you could possibly need. The gardens have multiple sitting areas for you glass of wine or cup of cappuccino! We came with children AND grandparents and it was perfect for everyone!!"
United States
aubry r.
Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome
Property grounds

5. 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
9.2 out of 10, Wonderful, (38 reviews)
"Wonderful location. Interesting villa. Beautiful views. Generous owner/manager."
United States
Carol L.
Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi
Outdoor dining

6. 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, (89 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
Property grounds

7. Old Tuscan house in the medieval village of Castiglione d'Orcia

Old Tuscan house in the medieval village of Castiglione d'Orcia
Castiglione d'Orcia
9.2 out of 10, Wonderful, (21 reviews)
"Great location"
United States
Bei
Old Tuscan house in the medieval village of Castiglione d'Orcia
Outdoor pool

8. 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 AED 457
AED 524 total
includes taxes & fees
2 Aug - 3 Aug
Casa Vacanze Le Case
Interior

9. Sweet home, the home of the small village

Sweet home, the home of the small village
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (11 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
View from property

10. Beautiful house on Chianti hilltop with exceptional views.

Beautiful house on Chianti hilltop with exceptional views.
Siena
10.0 out of 10, Exceptional, (75 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.
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.
Property grounds

12. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (75 reviews)
"Lovely charming home and town"
United States
Dana S.
The House of Alice, charm and relaxation
Outdoor pool

13. 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, (30 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!!!
Smart TV, fireplace

14. Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano

Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano
Montepulciano
9.8 out of 10, Exceptional, (9 reviews)
"Great place great location "
United States
Paul R.
Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano
Property grounds

15. Splendid farmhouse in Val d'Orcia with private swimming pool and sauna

Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
Radicofani
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed a relaxing time at you house. Close to a lot of nearby activities. "
United States
Michael B.
The price is AED 4,214
AED 5,313 total
includes taxes & fees
15 Aug - 16 Aug
Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
Property grounds

16. 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
Interior

17. 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
Property grounds

18. 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, (16 reviews)
"The setting is truly incredible! Stunning views, a well kept and comfortable house to stay in. We spent lots of family time in the pool and loved being just 15 minutes outside of Siena yet feeling so removed from everything. I highly recommend staying here!"
United States
Mark C.
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
3 bedrooms, in-room safe, desk, iron/ironing board

19. detached villa with private pool and garden

detached villa with private pool and garden
Castellina in Chianti
8.8 out of 10, Excellent, (29 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
Outdoor pool

20. Casa Rossella,charming house in historical Chianti Estate ,private pool

Casa Rossella,charming house in historical Chianti Estate ,private pool
San Gusme
10.0 out of 10, Exceptional, (53 reviews)
"Beautiful property. Great for a relaxing time in Tuscany"
United States
Peggy R.
Casa Rossella,charming house in historical Chianti Estate ,private pool
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

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Really nice hotel! The gardens at the back of the property were a really nice surprise!"
Jerome 1-night trip
Posted 9 hours ago
La Certosa di Pontignano

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