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

Roccastrada Vacation Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Roccastrada holiday rentals

A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

1. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is RM390
RM438 total
includes taxes & fees
9 Oct - 10 Oct
Country House il Ciliegio
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

2. Agriturismo Benvenuti

Agriturismo Benvenuti
Roccastrada
6.0 out of 10, (3 reviews)
"La stanza era molto grande e tranquilla. C'è anche un giardino abbastanza ampio a disposizione esclusiva di ogni camera/appartamento. Estrema cortesia. Ovviamente si è in aperta campagna, non in vicinanza del mare o dentro un borgo, ma in auto si raggiungo facilmente molte località interessanti del luogo. Su alcuni particolari, potrebbe essere tenuto un po' meglio, ma nel complesso ha un ottimo rapporto qualità/prezzo per la zona."
Italy
Ivano
The price is RM311
RM398 total
includes taxes & fees
1 Oct - 2 Oct
Agriturismo Benvenuti
An outdoor dining area with a table set for two, overlooking a lush green landscape and a hill in the distance.

3. Podere Cascatelle & Agriletizia

Podere Cascatelle & Agriletizia
Massa Marittima
10.0 out of 10, Exceptional, (2 reviews)
"Ótimo local, limpo, amplo, piscina boa, cascata boa, espaço amplo, adorei o local."
Brazil
Alan Cesar
The price is RM236
RM292 total
includes taxes & fees
30 Sept - 1 Oct
Podere Cascatelle & Agriletizia
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

4. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (5 reviews)
"Excellent boutique hotel with a very welcoming staff. Rooms were wonderful. Location was terrific - very easy short walk to restaurants in town. Would highly recommend"
United States
BRIAN
The price is RM1,587
RM1,783 total
includes taxes & fees
10 Sept - 11 Sept
Palazzo Saloni
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

5. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (13 reviews)
"The apartments and pool are fantastic. The location and breakfast boxes are perfect. The only real complaint was the parking lot was difficult to manage even in a smaller SUV. Staff were extremely communicative and made everything very easy for us."
United States
Ryan
The price is RM699
RM816 total
includes taxes & fees
5 Oct - 6 Oct
Corte Francigena - Apartments

6. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (7 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is RM557
RM627 total
includes taxes & fees
16 Sept - 17 Sept
Residence Arianna
A swimming pool with lounge chairs and an umbrella, surrounded by a wooden fence and trees.

7. Casale Vigna Carbona

Casale Vigna Carbona
Gavorrano
10.0 out of 10, Exceptional, (1 review)
"Cosa scrivere su questo magnifico angolo della maremma. Posto stupendo immerso nella natura, pulizia delle camere impeccabile così come la piscina se poi ci metti anche la cordialità di Luigi e di sua figlia Agnese padroni di casa impeccabili direi che non potevo scegliere posto migliore. Bravi, bravi , bravi "
Italy
Gennaro
The price is RM393
RM633 total
includes taxes & fees
12 Sept - 13 Sept
Casale Vigna Carbona
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

8. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (101 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is RM547
RM620 total
includes taxes & fees
15 Sept - 16 Sept
B&B Le Scalette di Piazza
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

9. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (178 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is RM454
RM538 total
includes taxes & fees
5 Oct - 6 Oct
Bosco della Spina
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

10. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is RM323
RM416 total
includes taxes & fees
26 Sept - 27 Sept
Tuscasì Aparthotel
A poolside area with two glasses of water, candles, and a stone pathway.

11. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (94 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is RM715
RM805 total
includes taxes & fees
13 Sept - 14 Sept
Casanova - Panoramic Rooms and Suites
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

12. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is RM520
RM610 total
includes taxes & fees
29 Sept - 30 Sept
Idolina Guest House
A large estate with multiple buildings, a swimming pool, and a well-maintained garden.

13. Dimora Santa Margherita - Boutique Hotel

Dimora Santa Margherita - Boutique Hotel
Cinigiano
8.2 out of 10, Very good, (11 reviews)
"The place was great! Food from their was amazing but also a bit expensive. Poolarea was so beautiful and the view was amazing! Only negative thing is that the wine tasting is not in hotel, need to take own car drive for that. Also the last 2km was sand road, which was not that good shape."
Finland
Anonymous traveller
The price is RM1,634
RM1,806 total
includes taxes & fees
27 Sept - 28 Sept
Dimora Santa Margherita - Boutique Hotel
A stone courtyard with a bench, potted plants, and a building in the background.

14. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is RM520
RM586 total
includes taxes & fees
29 Sept - 30 Sept
Casa di Campagna in Toscana

15. Residence Borgo San Lorenzo a Linari

Residence Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (99 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is RM420
RM486 total
includes taxes & fees
21 Sept - 22 Sept
Residence Borgo San Lorenzo a Linari
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

16. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is RM546
RM624 total
includes taxes & fees
29 Sept - 30 Sept
Borgo Il Poggiaccio
A spacious living area with a dining table, red chairs, and a small round table. Large windows provide natural light and views of greenery outside.

17. Residence Il Boschetto

Residence Il Boschetto
Grosseto
8.6 out of 10, Excellent, (8 reviews)
"The house is gorgeous! The area is very nice and the amenities were great! "
United States
Enrique
The price is RM366
RM417 total
includes taxes & fees
1 Oct - 2 Oct
Residence Il Boschetto
A pool area with lounge chairs and umbrellas, surrounded by lush greenery and overlooking a scenic view.

18. BeVedetta - Relais & Glamping - Adult Only

BeVedetta - Relais & Glamping - Adult Only
Scarlino
10.0 out of 10, Exceptional, (12 reviews)
"Loved it here!!!"
United States
Nina
The price is RM866
RM953 total
includes taxes & fees
2 Oct - 3 Oct
BeVedetta - Relais & Glamping - Adult Only
A traditional stone building with a courtyard, a staircase, and potted plants.

19. Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is RM428
RM490 total
includes taxes & fees
5 Oct - 6 Oct
Il Pozzo di Sant'Andrea
A table set with breakfast items on a balcony overlooking a historic town.

20. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (130 reviews)
"The room was very impressive with a large Chandelier. The breakfast was Delicious and the staff very very nice and helpful"
United States
Peggy
The price is RM1,257
RM1,402 total
includes taxes & fees
29 Sept - 30 Sept
Residenza d'Epoca Palazzo Borghesi
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"All the staff in the hotel were very helpful and we would like to stay there again."
Richard 2-night trip
Posted 4 hours ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Roccastrada

Search for holiday rentals in Roccastrada on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Roccastrada using one of the methods below:

  • View our selection of featured holiday rentals in Roccastrada
  • Use the map to find apartments and other holiday homes in the Roccastrada neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Roccastrada while they last

Look no further and take a look at our great range of rental properties in Roccastrada!

Frequently asked questions

Can I find holiday rentals in Roccastrada?

Yes, there are holiday rentals close to the most popular sights in Roccastrada, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Roccastrada?

Choose from 80 Expedia holiday rentals in Roccastrada for a memorable holiday.

What’s there to see and do in Roccastrada?

I Canaloni del Torrente Farma and Val di Merse are a couple of lovely local spots to get outside and enjoy nature. Podere Ristella Vineyards and Winery and Castello del Belagaio are other places to visit while you're in town.

What’s a holiday rental in Roccastrada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Roccastrada. Holiday rentals provide amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.