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

Roccastrada Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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 NZ$173
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 NZ$161
includes taxes & fees
23 Oct - 24 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, (3 reviews)
"Great for families, convenient parking and facilities, very tranquil."
United States
Ciarán
The price is NZ$198
includes taxes & fees
1 Oct - 2 Oct
Podere Cascatelle & Agriletizia
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

4. 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 NZ$265
includes taxes & fees
7 Oct - 8 Oct
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.

5. 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 NZ$175
includes taxes & fees
27 Oct - 28 Oct
Bosco della Spina
A bakery display with pastries and a coffee station.

6. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (211 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 NZ$231
includes taxes & fees
30 Sept - 1 Oct
B&B Il Corso
A covered outdoor seating area with wicker furniture, a table, and potted plants.

7. Fattoria San Lorenzo - Apartments

Fattoria San Lorenzo - Apartments
Grosseto
8.8 out of 10, Excellent, (30 reviews)
"Great, clean, and beautiful place."
United States
Aimee
The price is NZ$165
includes taxes & fees
13 Oct - 14 Oct
Fattoria San Lorenzo - Apartments
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

8. 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 NZ$370
includes taxes & fees
14 Oct - 15 Oct
Borgo Il Poggiaccio
A stone fountain with a light-up base, surrounded by grass and trees, with a building in the background.

9. Fattoria Pian di Rocca

Fattoria Pian di Rocca
Castiglione della Pescaia
9.6 out of 10, Exceptional, (34 reviews)
"We are very happy with everything in this hotel, nice room, comfortable bed, and very good breakfast."
Sweden
Tor
The price is NZ$179
includes taxes & fees
18 Oct - 19 Oct
Fattoria Pian di Rocca
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, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NZ$165
includes taxes & fees
25 Oct - 26 Oct
Tuscasì Aparthotel
A view from a window overlooking a cityscape with terracotta rooftops and a prominent dome structure in the distance.

11. A Casa Mastacchi

A Casa Mastacchi
Siena City Centre
7.8 out of 10, Good, (29 reviews)
"Christiana was the perfect hostess. Accommodations were quaint. Rooms and common areas were spotless. Breakfast and cafe were amazing. A true gem located in the heart of Siena. Close to shops, restaurants, and enotecas. I highly recommend you stay. "
United States
Christina
The price is NZ$246
includes taxes & fees
7 Oct - 8 Oct
A Casa Mastacchi
A traditional stone building with a courtyard, a staircase, and potted plants.

12. 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 NZ$197
includes taxes & fees
21 Oct - 22 Oct
Il Pozzo di Sant'Andrea
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.

13. 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 NZ$165
includes taxes & fees
5 Oct - 6 Oct
Residence Il Boschetto
A bathroom with a window view of a historic building and a tiled roof.

14. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (484 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is NZ$218
includes taxes & fees
21 Oct - 22 Oct
Siena Vip
A residential area with multiple buildings, a balcony with a wooden railing, and a view of trees and a clear sky.

15. Pineta Azzurra

Pineta Azzurra
Grosseto
8.0 out of 10, Very good, (13 reviews)
"Appartamento molto vicino al mare,per famiglie"
Italy
Lucrezia
The price is NZ$99
includes taxes & fees
30 Sept - 1 Oct
Pineta Azzurra
A couple seated at a table with drinks, overlooking a pool area with lounge chairs and umbrellas.

16. 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 NZ$432
includes taxes & fees
30 Sept - 1 Oct
Fattoria Maremmana
A hot tub with a digital interface, surrounded by a tiled wall and plants.

17. Residence Mareblu

Residence Mareblu
3.0 star property
Grosseto
8.6 out of 10, Excellent, (14 reviews)
"Very nice people running the hotel. Room was very clean and was big enough for 4 people. Very close to the beach."
United States
Anonymous traveller
The price is NZ$202
includes taxes & fees
1 Oct - 2 Oct
Residence Mareblu
A stone courtyard with a bench, potted plants, and a building in the background.

18. 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 NZ$199
includes taxes & fees
30 Oct - 31 Oct
Casa di Campagna in Toscana
A table with two wine glasses, a bottle, and a book.

19. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (98 reviews)
"Everything was very clean and modern, working perfect. We didn’t meet anyone from the staff. And it would be nice if they leave some bottle of water for each room. We like the place a lot. People have to consider that it is outside Siena walls and it’s a pretty steep and long distance walk"
United States
María
The price is NZ$138
includes taxes & fees
20 Oct - 21 Oct
Domus il Palio B&B
A modern hotel room with a wooden door, a white sink, a bathtub, a bed with white bedding, and a bedside table with a lamp.

20. Piazza Paradiso Accomodation

Piazza Paradiso Accomodation
Siena City Centre
9.2 out of 10, Wonderful, (161 reviews)
"Great location and lovely staff!"
United States
Dawn
The price is NZ$224
includes taxes & fees
22 Oct - 23 Oct
Piazza Paradiso Accomodation
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 Minerva

Hotel Minerva

10/10 Excellent
"If you are driving in Italy this is the best place to stay. Easy in and out with on site parking, zero stress! Easy walk into the heart of Siena. The staff were wonderful and the rooms clean."
Michael 1-night trip
Posted 2 days ago
Hotel Minerva

Find out more about Roccastrada

Everything you need to know about Roccastrada holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Roccastrada holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Roccastrada holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Roccastrada holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Roccastrada. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Roccastrada holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Roccastrada holiday rentals we have selected for you start as low as NZ$63 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Roccastrada rentals

At Expedia, we put the best Roccastrada holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Roccastrada rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Roccastrada holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Roccastrada. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

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

Casa Viale Italia - homely house with direct access to the sandy beach: This holiday home rental outside of Roccastrada is located near the beach, and has a patio, a garden and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Roccastrada?

Choose from 77 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.