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 Lucente with Mountain View, Pool, Garden & Wi-Fi

Roccastrada GR

HK$12,059 total

includes taxes & fees

1 Oct - 2 Oct

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

Roccastrada GR

HK$12,059 total

includes taxes & fees

8 Oct - 9 Oct

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

Roccastrada GR

HK$12,059 total

includes taxes & fees

1 Oct - 2 Oct

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

Roccastrada GR

HK$12,059 total

includes taxes & fees

1 Oct - 2 Oct

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

Gavorrano

HK$27,374 total

includes taxes & fees

19 Sept - 20 Sept

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

Toscana

"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."

Matthias W.

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

Montalcino

HK$53,662 total

includes taxes & fees

17 Sept - 18 Sept

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

Montenero

HK$5,697 total

includes taxes & fees

14 Oct - 15 Oct

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

Massa Marittima

HK$4,490 total

includes taxes & fees

5 Oct - 6 Oct

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

Porrona

HK$5,540 total

includes taxes & fees

18 Sept - 19 Sept

11. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

HK$49,411 total

includes taxes & fees

17 Sept - 18 Sept

12. 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$17,666 total

includes taxes & fees

29 Sept - 30 Sept

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

Follonica

Anonymous traveller

HK$4,726 total

includes taxes & fees

7 Oct - 8 Oct

14. Charming Tuscany Villa w/ Private Infinity Pool

Castel del Piano

HK$11,768 total

includes taxes & fees

17 Sept - 18 Sept

15. 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$6,862 total

includes taxes & fees

11 Oct - 12 Oct

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

Castiglione della Pescaia

Anonymous traveller

HK$3,330 total

includes taxes & fees

3 Oct - 4 Oct

17. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

HK$63,489 total

includes taxes & fees

17 Sept - 18 Sept

18. WPRELAIS BORGO VIGNALUNGA

Toscana

Jeremy F.

HK$13,207 total

includes taxes & fees

24 Sept - 25 Sept

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

Monteverdi Marittimo

HK$24,066 total

includes taxes & fees

27 Sept - 28 Sept

20. VILLA ALBA CHIARA - Six Bedroom Villa, Sleeps 12

Roccamare

HK$35,177 total

includes taxes & fees

17 Oct - 18 Oct

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Top Roccastrada Hotel Reviews

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"The villa is amazing and the perfect little world in itself. Its closeness to Siena makes it easier to visit the city. The patio is the perfect place to view Siena at sunset. The staff was very courteous and ready to help. This hotel is a gem."

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