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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Roccastrada villas

Exterior

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

Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
Roccastrada GR
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
Exterior

2. 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 €1,332
includes taxes & fees
1 Oct - 2 Oct
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
Exterior

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

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Exterior

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

Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
Pool

5. 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 €3,024
includes taxes & fees
20 Sept - 21 Sept
Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning
Exterior

6. Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups

Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups
Montenero
The price is €619
includes taxes & fees
14 Oct - 15 Oct
Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups
Exterior detail

7. 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 €496
includes taxes & fees
5 Oct - 6 Oct
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
Outdoor dining

8. 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 €489
includes taxes & fees
16 Oct - 17 Oct
Villa Gelsomino a Casa Conti di Sotto-Toscana mare piscine/spa- idromassaggio
Property grounds

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

VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Montalcino
The price is €5,928
includes taxes & fees
19 Sept - 20 Sept
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Property grounds

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 €612
includes taxes & fees
20 Sept - 21 Sept
Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning
Outdoor dining

11. 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 €1,952
includes taxes & fees
29 Sept - 30 Sept
Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi
Pool

12. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is €5,458
includes taxes & fees
20 Sept - 21 Sept
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Exterior

13. 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
Villa "Bouganville - Colleberto" with Sea View, Private Terrace & Wi-Fi
Property grounds

14. 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
Villa 'Paradiso' with Private Terrace, Private Garden and Wi-Fi
Property grounds

15. Charming Tuscany Villa w/ Private Infinity Pool

Charming Tuscany Villa w/ Private Infinity Pool
Castel del Piano
The price is €1,320
includes taxes & fees
19 Sept - 20 Sept
Charming Tuscany Villa w/ Private Infinity Pool
Exterior

16. WPRELAIS BORGO VIGNALUNGA

WPRELAIS BORGO VIGNALUNGA
Toscana
10.0 out of 10, Exceptional, (39 reviews)
"This villa is amazing! The views are spectacular. The home is awesome! The property is beautiful! "
United States
Jeremy F.
The price is €1,427
includes taxes & fees
24 Sept - 25 Sept
WPRELAIS BORGO VIGNALUNGA
Property grounds

17. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Siena
The price is €7,014
includes taxes & fees
19 Sept - 20 Sept
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Terrace/patio

18. 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 €2,659
includes taxes & fees
27 Sept - 28 Sept
Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
Outdoor dining

19. Villa Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is €2,769
includes taxes & fees
18 Oct - 19 Oct
Villa Mami: A Tuscan Retreat of Elegance and Charm
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

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Perfect hotel. Quiet, safe, great location, staff was fabulous, breakfast was very good. This hotel had it all. Highly recommend."
Shannon 3-night trip
Posted 1 day ago
Hotel Chiusarelli

Find out more about Roccastrada

Roccastrada Villas information

Number of reviews
65
Accommodation
542 Villas
Lowest Price
€489
Highest Price
€7,014