Roccastrada Vacation Rentals from ￥5,718: Search Short-Term Rentals

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

Agriturismo Campo al Crognolo. : This Roccastrada vacation home rental is located in a rural location and has an outdoor pool, a fireplace, and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

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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

Roccastrada

Maaike

￥15,805 total

includes taxes & fees

Oct 9 - Oct 10

A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

2. Agriturismo Benvenuti

Roccastrada

"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."

Ivano

￥15,108 total

includes taxes & fees

Oct 1 - Oct 2

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

Massa Marittima

Ciarán

￥10,788 total

includes taxes & fees

Sep 30 - Oct 1

A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

4. Palazzo Saloni

Montalcino

BRIAN

￥62,075 total

includes taxes & fees

Sep 15 - Sep 16

A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

5. Corte Francigena - Apartments

Montalcino

Ryan

￥28,747 total

includes taxes & fees

Oct 5 - Oct 6

6. Residence Arianna

Sovicille

"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...

Gitte Harrits

￥22,888 total

includes taxes & fees

Oct 11 - Oct 12

A swimming pool with lounge chairs and an umbrella, surrounded by a wooden fence and trees.

7. Casale Vigna Carbona

Gavorrano

Gennaro

￥22,036 total

includes taxes & fees

Sep 26 - Sep 27

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

Montalcino

François

￥22,833 total

includes taxes & fees

Sep 14 - Sep 15

An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

9. Bosco della Spina

Murlo

Lizl

￥20,387 total

includes taxes & fees

Oct 5 - Oct 6

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

Sovicille

Sergey

￥15,805 total

includes taxes & fees

Sep 28 - Sep 29

A poolside area with two glasses of water, candles, and a stone pathway.

11. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

Jarkko

￥29,104 total

includes taxes & fees

Sep 17 - Sep 18

A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

12. Idolina Guest House

Montalcino

Bradley

￥24,099 total

includes taxes & fees

Sep 13 - Sep 14

A large estate with multiple buildings, a swimming pool, and a well-maintained garden.

13. Dimora Santa Margherita - Boutique Hotel

Cinigiano

Anonymous traveler

￥56,467 total

includes taxes & fees

Oct 5 - Oct 6

A stone courtyard with a bench, potted plants, and a building in the background.

14. Casa di Campagna in Toscana

Sovicille

Sally

￥21,218 total

includes taxes & fees

Oct 2 - Oct 3

15. Residence Borgo San Lorenzo a Linari

Sovicille

Monica

￥23,347 total

includes taxes & fees

Sep 21 - Sep 22

An interior with stone walls, wooden doors, and a bar area with stools and bottles.

16. Borgo Il Poggiaccio

Sovicille

Louie

￥23,700 total

includes taxes & fees

Sep 29 - Sep 30

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

Grosseto

Enrique

￥15,214 total

includes taxes & fees

Oct 11 - Oct 12

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and overlooking a scenic view.

18. BeVedetta - Relais & Glamping - Adult Only

Scarlino

Nina

￥36,131 total

includes taxes & fees

Oct 2 - Oct 3

A traditional stone building with a courtyard, a staircase, and potted plants.

19. Il Pozzo di Sant'Andrea

Siena

Prem

￥18,401 total

includes taxes & fees

Oct 5 - Oct 6

A table set with breakfast items on a balcony overlooking a historic town.

20. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Peggy

￥51,565 total

includes taxes & fees

Sep 29 - Sep 30

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Top Roccastrada Hotel Reviews

Hotel Athena

8/10 Good

"Overall okay hotel. It’s meant more to come in during the morning while explore and out all day. Rooms are small and you can hear everything that’s going on in the hallway and in othe rooms (e.g., crying baby at 3am). Reception staff (Simone) was helpful and bartender (Lucas) was super nice. View in the terrace is good and peaceful but can’t be use if too close to dinner time."

Castello di Velona Resort Thermal SPA & Winery

8/10 Good

"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!"

The Sense Experience Resort - Preferred Hotels & Resorts

10/10 Excellent

"Great property, classy, staff crew are professionals. Egor is great. Staff remembers from year to year. Management is awesome and helpful all the time The manager Sylvia is a friendly and helpful. All over staff, front desk, waiters, cleaners, managements, and bellboys are the best of the best. Only missing thing in this hotel is a Gym , but they do some classes, but gym is needed to make it as a cherry on the top. Breakfast is great , dinners are lovely. We keep going there every year."

Find out more about Roccastrada

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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?

Agriturismo Campo al Crognolo.: This Roccastrada vacation home rental is located in a rural location and has an outdoor pool, a fireplace, and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Roccastrada?

Choose from 79 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.

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Check prices for these dates

Our top choices for Roccastrada vacation rentals

1. Country House il Ciliegio

2. Agriturismo Benvenuti

3. Podere Cascatelle & Agriletizia

4. Palazzo Saloni

5. Corte Francigena - Apartments

6. Residence Arianna

7. Casale Vigna Carbona

8. B&B Le Scalette di Piazza

9. Bosco della Spina

10. Tuscasì Aparthotel

11. Casanova - Panoramic Rooms and Suites

12. Idolina Guest House

13. Dimora Santa Margherita - Boutique Hotel

14. Casa di Campagna in Toscana

15. Residence Borgo San Lorenzo a Linari

16. Borgo Il Poggiaccio

17. Residence Il Boschetto

18. BeVedetta - Relais & Glamping - Adult Only

19. Il Pozzo di Sant'Andrea

20. Residenza d'Epoca Palazzo Borghesi

Find vacation rentals that suit your style

Top Roccastrada Hotel Reviews

Hotel Athena

NH Siena

Castello di Velona Resort Thermal SPA & Winery

Villa Scacciapensieri Boutique Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Chiusarelli

The Sense Experience Resort - Preferred Hotels & Resorts

Il Chiostro del Carmine

L'Orto delle Terme

Find out more about Roccastrada

Frequently asked questions

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