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

Holiday 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 town with tightly packed buildings, a prominent tower, and a church.
Holiday HomesHoliday Homes

Siena

Siena

Our top choices for Province of Siena holiday homes

Deluxe Apartment

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
Property grounds

2. 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
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. 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, (41 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
Outdoor dining

5. 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
Interior

6. 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
View from property

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.
Smart TV, fireplace

8. 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, (10 reviews)
"Great place great location "
United States
Paul R.
Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano
Outdoor pool

9. 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
Property grounds

10. 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, ping pong

11. 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
Interior

12. 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

13. 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
Property grounds

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, (16 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
Outdoor dining

15. Tuscan Hilltop Terrace-Poliziano 7

Tuscan Hilltop Terrace-Poliziano 7
Montepulciano
10.0 out of 10, Exceptional, (1 review)
"Stunning apartment with jaw dropping views. Every single thing was thought of"
United States
Natalie L.
Tuscan Hilltop Terrace-Poliziano 7
Outdoor dining

16. GuestHost - Beautiful studio of 25 square meters located on the first floor of a building without elevator (6 steps to access), can comfortably accommodate up to 2 people.The property is located in the historic center (Restricted Traffic Zone), just outs

GuestHost - Beautiful studio of 25 square meters located on the first floor of a building without elevator (6 steps to access), can comfortably accommodate up to 2 people.The property is located in the historic center (Restricted Traffic Zone), just outs
Siena Historical Center
10.0 out of 10, Exceptional, (1 review)
"Traveling in July in Italy was going to be hot, but we didn’t realize how taxing it would be. To our utter astonishment and delight this darling apartment had been equipped with a brand new a/c. It literally saved our lives (and our vacay)! Clean, modern, darling- exactly as advertised!"
United States
Martha N.
GuestHost - Beautiful studio of 25 square meters located on the first floor of a building without elevator (6 steps to access), can comfortably accommodate up to 2 people.The property is located in the historic center (Restricted Traffic Zone), just outs
Outdoor pool

17. 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
Property grounds

18. Holiday at Poggettone

Holiday at Poggettone
Monteroni d'Arbia
Holiday at Poggettone
Pool

19. TYPICAL FARM HOUSE WITH POOL IN CHIANTI NEAR SIENA, FLORENCE ..

TYPICAL FARM HOUSE WITH POOL IN CHIANTI NEAR SIENA, FLORENCE ..
MONTERIGGIONI
9.0 out of 10, Wonderful, (2 reviews)
"Lovely home in a lovely area"
United States
jude d.
TYPICAL FARM HOUSE WITH POOL IN CHIANTI NEAR SIENA, FLORENCE ..
House | Pool

20. Tasteful Countryside Stay

Tasteful Countryside Stay
Montalcino
Tasteful Countryside Stay
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

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Lovely historic hotel, certainly captured the essence of the period it was built in. Room was spacious, beds very comfortable and considering the average temp was 35 degrees for the 3 nights we stayed, the air conditioning worked well enough. C The"
Mark 3-night trip
Posted 7 hours ago
Palazzo Ravizza

Find out more about Province of Siena

Province of Siena Holiday Homes information

Number of reviews
605
Accommodation
979 Holiday Homes
Lowest Price
Highest Price

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