An ancient stone tower with a view of rolling hills and fields in the background.

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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

Our top choices for Roccastrada villas

A two-story house with a stone facade, a tiled roof, and a well-maintained lawn.

1. Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is £1,145
includes taxes & fees
1 Oct - 2 Oct
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
A two-story house with a stone facade, a tiled roof, and a well-maintained lawn.

2. Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi

Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
Roccastrada GR
The price is £1,145
includes taxes & fees
1 Oct - 2 Oct
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
A two-story house with a stone facade, a tiled roof, and a well-maintained lawn.

3. Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is £1,145
includes taxes & fees
3 Oct - 4 Oct
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
A house with a stone wall, a large tree, and a patio area with a bench and table.

4. Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is £1,145
includes taxes & fees
3 Oct - 4 Oct
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
A gazebo with a thatched roof overlooking a scenic landscape.

5. Villa Gelsomino a Casa Conti di Sotto-Toscana mare piscine/spa- idromassaggio

Villa Gelsomino a Casa Conti di Sotto-Toscana mare piscine/spa- idromassaggio
Toscana
9.8 out of 10, Exceptional, (21 reviews)
"Posto magnifico, le ville molto curate e pulite, con tutto il necessario e anche di più. La posizione davvero ottima, si arriva in un attimo in paese e in pochi minuti di auto si può raggiungere la costa. Consigliatissimo, sicuramente ritorneremo anche con la bella stagione."
Italy
Giulia O.
The price is £280
includes taxes & fees
29 Sept - 30 Sept
Villa Gelsomino a Casa Conti di Sotto-Toscana mare piscine/spa- idromassaggio
A clear pool with lounge chairs, a wooden deck, and a view of hills in the background.

6. Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning

Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning
Gavorrano
The price is £2,600
includes taxes & fees
30 Sept - 1 Oct
Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning
A wooden deck with a glass enclosure overlooking a mountainous landscape.

7. Villa Biancospino to Casa Conti di Sotto, private heated hydromassage,sea,spa

Villa Biancospino to Casa Conti di Sotto, private heated hydromassage,sea,spa
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"It was a very nice vacation at Casa Conti Di Sotto. The VIP area is really private, you only have one neighbour in the other part of the house. The house and garden are well equipped. The main house is located a few meters away from the VIP area. There are all the other things like swimming pool and sauna. The upper part at the sauna has a nice view of the landscape. Vasile was also very nice and helpful."
Germany
Matthias W.
The price is £281
includes taxes & fees
1 Oct - 2 Oct
Villa Biancospino to Casa Conti di Sotto, private heated hydromassage,sea,spa
A stone house with a tiled roof, a small porch, and potted plants.

8. Quercetino: An Authentic Tuscan Country House Near Val d'Orcia & Hot Springs - Sleeps 10

Quercetino: An Authentic Tuscan Country House Near Val d'Orcia & Hot Springs - Sleeps 10
Montenero
The price is £516
includes taxes & fees
26 Oct - 27 Oct
Quercetino: An Authentic Tuscan Country House Near Val d'Orcia & Hot Springs - Sleeps 10
A stone building with a garden pathway leading to it.

9. VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Montalcino
The price is £5,097
includes taxes & fees
29 Sept - 30 Sept
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
A stone wall, a pine tree, and a view of a green valley with hills.

10. Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning

Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning
Porrona
The price is £461
includes taxes & fees
6 Oct - 7 Oct
Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning
A stone exterior wall, a glass door entrance, and a brick pathway leading to a staircase.

11. Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center

Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
Massa Marittima
The price is £409
includes taxes & fees
5 Oct - 6 Oct
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
A stone building with balconies, a gravel path, and a tree.

12. Villa "Bouganville - Colleberto" with Sea View, Private Terrace & Wi-Fi

Villa "Bouganville - Colleberto" with Sea View, Private Terrace & Wi-Fi
Follonica
10.0 out of 10, Exceptional, (1 review)
"Pros: La vue proximité mer et ville superbe villa vue sur mer"
France
Anonymous traveller
The price is £449
includes taxes & fees
7 Oct - 8 Oct
Villa "Bouganville - Colleberto" with Sea View, Private Terrace & Wi-Fi
A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

13. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is £4,694
includes taxes & fees
29 Sept - 30 Sept
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
A table with a red and white checkered tablecloth, a hanging light fixture, and a view of green hills and trees.

14. Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi

Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi
Murlo
10.0 out of 10, Exceptional, (1 review)
"Our stay at this property was absolutely excellent! The home was spotless, beautifully decorated, and even more spacious than the photos showed. Every amenity listed was fully functional, and the brand new swimming pool was amazing. The location was perfect— isolated peaceful and quiet, yet just a short drive from the Buonconvento .The host was wonderful to work with. Communication was lightning-fast, and the check-in and checkout instructions were crystal clear. They truly went above and beyond...
United States
martina p.
The price is £2,799
includes taxes & fees
29 Sept - 30 Sept
Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi
A yellow building with a tiled walkway leading to a door, flanked by two small, colorful lighthouse models.

15. Villa 'Paradiso' with Private Terrace, Private Garden and Wi-Fi

Villa 'Paradiso' with Private Terrace, Private Garden and Wi-Fi
Castiglione della Pescaia
8.0 out of 10, Very good, (3 reviews)
"Pros: Die Gastfreundlichkeit des Vermieters vor Ort. Die ruhige, schöne Lage. Toll ausgestattete Ferienwohnung mit wunderbarem Rundumblick."
Germany
Anonymous traveller
The price is £316
includes taxes & fees
3 Oct - 4 Oct
Villa 'Paradiso' with Private Terrace, Private Garden and Wi-Fi
A stone building with a car parked in front, surrounded by trees and a gravel path.

16. Charming Tuscany Villa w/ Private Infinity Pool

Charming Tuscany Villa w/ Private Infinity Pool
Castel del Piano
The price is £1,136
includes taxes & fees
29 Sept - 30 Sept
Charming Tuscany Villa w/ Private Infinity Pool
A covered outdoor area with a pool, wicker furniture, and a view of the countryside.

17. Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning

Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
Monteverdi Marittimo
The price is £2,286
includes taxes & fees
30 Sept - 1 Oct
Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
A brick building with a gravel courtyard, a staircase, and potted plants.

18. GuestHost - Porta Romana Elegant House with Private Parking!

GuestHost - Porta Romana Elegant House with Private Parking!
Siena
9.0 out of 10, Wonderful, (4 reviews)
"Excellent location 15 mi minute walk to the center of town. Towels and linens were fresh and fragrant. On site parking was super convenient because of limited parking around the town. The property manager was immediately available by phone and delivered an extra blanket which in 5 minutes of our request."
United States
Kathleen M.
The price is £269
includes taxes & fees
5 Oct - 6 Oct
GuestHost - Porta Romana Elegant House with Private Parking!
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

19. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is £6,031
includes taxes & fees
30 Sept - 1 Oct
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
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 Roccastrada Hotel Reviews

Four Points by Sheraton Siena

Four Points by Sheraton Siena

10/10 Excellent
"Excellent property. It was well maintained, and the staff was friendly. I would definitely stay here again."
Ralph 1-night trip
Posted 11 hours ago
Four Points by Sheraton Siena

Find out more about Roccastrada

Roccastrada Villas information

Number of reviews
33
Accommodation
542 Villas
Lowest Price
£269
Highest Price
£6,031