Roccastrada Villas

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

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Our top choices for Roccastrada villas

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

Roccastrada GR

HK$11,983 total

includes taxes & fees

8 Oct - 9 Oct

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

Roccastrada GR

HK$11,983 total

includes taxes & fees

1 Oct - 2 Oct

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

Roccastrada GR

HK$11,983 total

includes taxes & fees

1 Oct - 2 Oct

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

Roccastrada GR

HK$11,983 total

includes taxes & fees

1 Oct - 2 Oct

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

Gavorrano

HK$27,201 total

includes taxes & fees

20 Sept - 21 Sept

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

Montenero

HK$5,661 total

includes taxes & fees

14 Oct - 15 Oct

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

Massa Marittima

HK$4,462 total

includes taxes & fees

5 Oct - 6 Oct

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

Toscana

Giulia O.

HK$4,435 total

includes taxes & fees

16 Oct - 17 Oct

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

Montalcino

HK$53,323 total

includes taxes & fees

19 Sept - 20 Sept

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

Porrona

HK$5,505 total

includes taxes & fees

19 Sept - 20 Sept

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

Murlo

"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...

martina p.

HK$17,554 total

includes taxes & fees

29 Sept - 30 Sept

12. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

HK$49,099 total

includes taxes & fees

19 Sept - 20 Sept

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

Follonica

Anonymous traveller

HK$4,696 total

includes taxes & fees

7 Oct - 8 Oct

14. Wp Relais Villa Vignalunga

CASTIGLIONE D'ORCIA (SI)

"Incredible stay! Property was beautifully restored and outfitted, and immaculately clean when we arrived. The host was very responsive, helping us bring in a local chef and responded quickly to our various questions during our stay. The heated pool was wonderful. The property was the right size for seven guests. We hope to return because six nights here wasn’t enough! I wish there was an option to give higher than five stars!"

Marshall W.

HK$6,818 total

includes taxes & fees

11 Oct - 12 Oct

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

Castiglione della Pescaia

Anonymous traveller

HK$3,309 total

includes taxes & fees

3 Oct - 4 Oct

16. Charming Tuscany Villa w/ Private Infinity Pool

Castel del Piano

HK$11,694 total

includes taxes & fees

19 Sept - 20 Sept

17. WPRELAIS BORGO VIGNALUNGA

Toscana

Jeremy F.

HK$13,178 total

includes taxes & fees

24 Sept - 25 Sept

18. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

HK$63,089 total

includes taxes & fees

19 Sept - 20 Sept

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

Monteverdi Marittimo

HK$23,914 total

includes taxes & fees

4 Oct - 5 Oct

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

Toscana

HK$24,440 total

includes taxes & fees

18 Oct - 19 Oct

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Top Roccastrada Hotel Reviews

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."

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good

"Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty."

Palazzo Ravizza

10/10 Excellent

"We had a wonderful time at this hotel. Everything was excellent and everyone so helpful. Great room ,that had a wonderful view of the gardens . The room was very clean and well equipt with all you need to enjoy your stay. Walkable access to the centre with some lovely shops ,bars and restaurants on the way. A massive thank you to Francesca who was brilliant. So knowledgable about the area and friendly and helpful. Her and the team are doing a wonderful job. Would highly recommend and I would visit again."

Grand Hotel Bastiani

10/10 Excellent

"The breakfast buffet was absolutely delicious, the barista made the best cappuccinos! The rooms are clean and beautiful. The bathrooms are glorious, glorious. The bathtubs are deep and long, for a luxurious soak after a long day of walking in the old town. This is close to cafés and Gelateria’s. Front desk staff are kind and allowed us an hour extra checkout."

Find out more about Roccastrada