Roccastrada Vacation Rentals from $33: Search Short-Term Rentals

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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

$103 nightly

Sep 22 - Sep 23

Total with taxes and fees

A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

2. B&B Le Scalette di Piazza

Montalcino

François

$126 nightly

Sep 29 - Sep 30

Total with taxes and fees

A view from a window overlooking a cityscape with terracotta rooftops and a prominent dome structure in the distance.

3. A Casa Mastacchi

Siena City Centre

Christina

$122 nightly

Sep 29 - Sep 30

Total with taxes and fees

A bakery display with pastries and a coffee station.

4. B&B Il Corso

Siena City Centre

Enrique

$117 nightly

Sep 3 - Sep 4

Total with taxes and fees

A covered outdoor seating area with wicker furniture, a table, and potted plants.

5. Fattoria San Lorenzo - Apartments

Grosseto

Aimee

$122 nightly

Sep 18 - Sep 19

Total with taxes and fees

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

6. Il Pozzo di Sant'Andrea

Siena

Prem

$112 nightly

Sep 3 - Sep 4

Total with taxes and fees

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

7. Borgo Il Poggiaccio

Sovicille

Louie

$220 nightly

Sep 17 - Sep 18

Total with taxes and fees

A bathroom with a window view of a historic building and a tiled roof.

8. Siena Vip

Siena City Centre

Luis

$113 nightly

Aug 30 - Aug 31

Total with taxes and fees

A stone fountain with a light-up base, surrounded by grass and trees, with a building in the background.

9. Fattoria Pian di Rocca

Castiglione della Pescaia

Jose Pedro

$115 nightly

Sep 23 - Sep 24

Total with taxes and fees

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.

10. Residence Il Boschetto

Grosseto

Enrique

$99 nightly

Sep 27 - Sep 28

Total with taxes and fees

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

11. Casa di Campagna in Toscana

Sovicille

Sally

$124 nightly

Sep 2 - Sep 3

Total with taxes and fees

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

$120 nightly

Sep 1 - Sep 2

Total with taxes and fees

A bedroom with a bed, bedside table, and a window with a view of greenery.

13. La Coroncina Lodging

Siena

Hassan

$128 nightly

Aug 31 - Sep 1

Total with taxes and fees

A modern lobby with white leather sofas, a glass coffee table, and potted plants.

14. ApartHotel Anghel

Siena

jon

$93 nightly

Aug 30 - Aug 31

Total with taxes and fees

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.

15. Tuscasì Aparthotel

Sovicille

Sergey

$90 nightly

Sep 26 - Sep 27

Total with taxes and fees

A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

16. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

San Quirico d'Orcia

Elena

$101 nightly

Aug 30 - Aug 31

Total with taxes and fees

A table with two wine glasses, a bottle, and a book.

17. Domus il Palio B&B

Ravacciano

Alissia

$81 nightly

Sep 24 - Sep 25

Total with taxes and fees

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

18. Bosco della Spina

Murlo

Lizl

$141 nightly

Sep 24 - Sep 25

Total with taxes and fees

A building with a sign reading 'Villa Le Camelie' and multiple flags.

19. Villa le Camelie Siena

Petriccio

Mark

$84 nightly

Aug 30 - Aug 31

Total with taxes and fees

A bedroom with a bed, wooden floor, and two bedside lamps.

20. Guest House All'83

Grosseto

Orlando

$88 nightly

Aug 30 - Aug 31

Total with taxes and fees

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Top Roccastrada Hotel Reviews

Palazzo Ravizza

10/10 Excellent

"Wonderful hotel hopefully be back"

Castello di Leonina Relais

10/10 Excellent

"We stayed 4 days and are so glad we stayed here. The area has a restaurant right outside with the best view where they serve lunch and dinner. They also have a bar and a pool. It’s an old castle and yet they keep it clean and pretty restored. Breakfast buffet in the morning was included for us. The bathroom comment from others might be from not understanding how to use it as you have to pump the button several times to flush. The staff was wonderful and helpful. They spoke English and some Spanish."

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. The food was delicious and every waitstaff that we encountered was polite and attentive--it could not have been a better experience."

Find out more about Roccastrada

Everything you need to know about Roccastrada vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Roccastrada vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Roccastrada vacation 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 low season months. For more hustle and bustle, you may prefer to visit Roccastrada in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $33 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Roccastrada rentals

At Expedia, we put the best Roccastrada vacation 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 vacation.

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.

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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?

Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi: This vacation home rental near Roccastrada is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private balcony, a terrace, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Roccastrada?

Choose from 80 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.

Roccastrada Vacation Rentals

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Check prices for these dates

Our top choices for Roccastrada vacation rentals

1. Country House il Ciliegio

2. B&B Le Scalette di Piazza

3. A Casa Mastacchi

4. B&B Il Corso

5. Fattoria San Lorenzo - Apartments

6. Il Pozzo di Sant'Andrea

7. Borgo Il Poggiaccio

8. Siena Vip

9. Fattoria Pian di Rocca

10. Residence Il Boschetto

11. Casa di Campagna in Toscana

12. Idolina Guest House

13. La Coroncina Lodging

14. ApartHotel Anghel

15. Tuscasì Aparthotel

16. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

17. Domus il Palio B&B

18. Bosco della Spina

19. Villa le Camelie Siena

20. Guest House All'83

Find vacation rentals that suit your style

Top Roccastrada Hotel Reviews

Palazzo Ravizza

Find out more about Roccastrada

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