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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Roccastrada vacation 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 AED 327
AED 368 total
includes taxes & fees
23 Oct - 24 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 AED 257
AED 332 total
includes taxes & fees
23 Oct - 24 Oct
Agriturismo Benvenuti
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.

3. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is AED 229
AED 306 total
includes taxes & fees
2 Nov - 3 Nov
Tuscasì Aparthotel
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

4. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (183 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 AED 296
AED 358 total
includes taxes & fees
27 Oct - 28 Oct
Bosco della Spina
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

5. Palazzo Saloni

Palazzo Saloni
Montalcino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is AED 808
AED 930 total
includes taxes & fees
8 Nov - 9 Nov
Palazzo Saloni
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

6. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (251 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
The price is AED 370
AED 423 total
includes taxes & fees
2 Nov - 3 Nov
La Terrazza Sul Campo Rooming House
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

7. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (222 reviews)
"The room was so unique and convenient for everything we wanted to do. Wish we could have spent more than one night!"
United States
Kellie
The price is AED 487
AED 552 total
includes taxes & fees
5 Nov - 6 Nov
Il Battistero Siena - Residenza d'Epoca
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

8. 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 AED 291
AED 354 total
includes taxes & fees
25 Oct - 26 Oct
Idolina Guest House
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

9. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (105 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is AED 431
AED 491 total
includes taxes & fees
14 Oct - 15 Oct
B&B Le Scalette di Piazza
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

10. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (116 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
The price is AED 667
AED 751 total
includes taxes & fees
3 Nov - 4 Nov
PALAZZO DEL PAPA
A table set with breakfast items on a balcony overlooking a historic town.

11. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (132 reviews)
"We had a great experience Property is perfectly located."
United States
Roman
The price is AED 519
AED 587 total
includes taxes & fees
4 Nov - 5 Nov
Residenza d'Epoca Palazzo Borghesi
A hotel room with a bed, a desk, a chair, a window with curtains, a wall-mounted lamp, and a potted plant.

12. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (213 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is AED 415
AED 473 total
includes taxes & fees
1 Nov - 2 Nov
B&B Il Corso
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, (12 reviews)
"We had a great time at this place. The room was spectacular and the views were some of the best on this entire trip. We would definitely come back. The only thing that we didn’t love was the menu at the restaurant is quite limited and there were not many things on the menu that appealed to us, as we were looking for more traditional Tuscan food. Breakfast was great and very traditional. The staff was fantastic and very helpful. Loved it."
Canada
Nicole
The price is AED 1,117
AED 1,237 total
includes taxes & fees
25 Oct - 26 Oct
Dimora Santa Margherita - Boutique Hotel
A poolside area with two glasses of water, candles, and a stone pathway.

14. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (101 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
The price is AED 614
AED 692 total
includes taxes & fees
30 Oct - 31 Oct
Casanova - Panoramic Rooms and Suites
A couple seated at a table with drinks, overlooking a pool area with lounge chairs and umbrellas.

15. Fattoria Maremmana

Fattoria Maremmana
4.0 star property
Grosseto
8.0 out of 10, Very good, (11 reviews)
"Staff very friendly and helpful. Very quiet stay as we visited at the beginning of the slow season. "
United States
James
The price is AED 794
AED 889 total
includes taxes & fees
9 Oct - 10 Oct
Fattoria Maremmana
Outdoor pool

16. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
The price is AED 530
AED 596 total
includes taxes & fees
10 Oct - 11 Oct
Residence Arianna
A detailed architectural molding with a symmetrical design.

17. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (486 reviews)
"Great location right in the heart of everything and next to an escalator that takes you to the main plaza. Very comfortable bed, friendly staff. Convenient parking option very close by."
United States
Heather
The price is AED 394
AED 450 total
includes taxes & fees
21 Oct - 22 Oct
Siena Vip
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

18. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (19 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is AED 445
AED 522 total
includes taxes & fees
8 Nov - 9 Nov
Corte Francigena - Apartments
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

19. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (54 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is AED 512
AED 579 total
includes taxes & fees
8 Nov - 9 Nov
Guild Living Siena Senior Resort & Residence
A stone courtyard with a bench, potted plants, and a building in the background.

20. 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 AED 362
AED 410 total
includes taxes & fees
30 Oct - 31 Oct
Casa di Campagna in Toscana
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
"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."
JOHN 3-night trip
Posted 2 days ago
Grand Hotel Continental Siena – Starhotels Collezione

Frequently asked questions

Can I find vacation rentals in Roccastrada?

Yes, we give you a choice of vacation rentals close to well known points of interest in Roccastrada, or you can choose a secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Roccastrada has to offer?

Casa Viale Italia - homely house with direct access to the sandy beach: This vacation home rental near Roccastrada is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Roccastrada?

Choose from 77 Expedia vacation rentals in Roccastrada for a memorable vacation.

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 vacation rental in Roccastrada like?

Vacation rentals are private properties where you can stay for several days or longer in Roccastrada. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for family trips or small group gatherings.