Roccastrada Vacation Rentals from $51: Search Short-Term Rentals

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Our top choices for Roccastrada vacation rentals

A window with a view of a green landscape and a clear sky.

1. Casa Giovy - A family-friendly village nestled among the hills, the sea, and hot springs in the Tuscan Maremma

Roccastrada

$94 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

2. Country House il Ciliegio

Roccastrada

Maaike

$86 nightly

Nov 13 - Nov 14

Total with taxes and fees

A stone building with multiple windows and a balcony.

3. Giacinto – Classic Double Room

Piloni

$125 nightly

Nov 9 - Nov 10

Total with taxes and fees

A vineyard with rows of grapevines, a house with a red roof, and a clear view of distant hills.

4. Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi

Roccastrada

$6,636 nightly

Nov 9 - Nov 10

Total with taxes and fees

5. Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi

Roccastrada GR

$1,480 nightly

Nov 9 - Nov 10

Total with taxes and fees

A rustic outdoor seating area with a wooden pergola, stone walls, and potted plants.

6. Uva Spina – Intimate Double Room with Val di Farma View

Piloni

$140 nightly

Nov 9 - Nov 10

Total with taxes and fees

7. Deluxe Room 'Narciso Dei Poeti' with Extra Bed

Piloni

$170 nightly

Nov 9 - Nov 10

Total with taxes and fees

8. Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View

Piloni

$186 nightly

Nov 9 - Nov 10

Total with taxes and fees

A bathroom with a sink, mirror, and two toilets.

9. Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

Roccastrada GR

$1,480 nightly

Nov 9 - Nov 10

Total with taxes and fees

10. Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

Roccastrada GR

$1,480 nightly

Nov 9 - Nov 10

Total with taxes and fees

11. Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi

Roccastrada GR

$1,480 nightly

Nov 9 - Nov 10

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.

12. Tuscasì Aparthotel

Sovicille

Sergey

$72 nightly

Nov 20 - Nov 21

Total with taxes and fees

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

13. Idolina Guest House

Montalcino

Jaiden

$94 nightly

Dec 9 - Dec 10

Total with taxes and fees

A hotel lobby with a reception desk, seating area, bookshelves, and large windows.

14. Appartamenti La Vecchia Posta

Marina di Grosseto

$61 nightly

Dec 3 - Dec 4

Total with taxes and fees

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

15. Casa di Campagna in Toscana

Sovicille

Sally

$83 nightly

Nov 15 - Nov 16

Total with taxes and fees

A dining area with a rustic brick wall, wooden ceiling beams, and a table with a vase of flowers.

16. B&B Le Scalette di Piazza

Montalcino

Morris

$119 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern bedroom with a wooden floor, a bed with white linens, a bedside table, a mirror, and a TV mounted on the wall.

17. Botrona B&B

Scarlino

Anna

$80 nightly

Nov 11 - Nov 12

Total with taxes and fees

A residential area with multiple buildings, a balcony with a wooden railing, and a view of trees and a clear sky.

18. Pineta Azzurra

Grosseto

Lucrezia

$47 nightly

Nov 13 - Nov 14

Total with taxes and fees

An open door leading to a balcony with a view of a forested hillside.

19. La Dimora di Dida

Seggiano

$71 nightly

Nov 21 - Nov 22

Total with taxes and fees

A courtyard with outdoor seating, a building with multiple windows, and a stone wall.

20. Palazzo Saloni

Montalcino

Michael

$254 nightly

Dec 9 - Dec 10

Total with taxes and fees

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Top Roccastrada Hotel Reviews

L'Orto delle Terme

10/10 Excellent

"Bed and breakfast is very convenient. alternative to the main hotel. Rooms are very good and have access to the main hotel restaurant for breakfast. If you want to use their spa facilities and stay in the bed and breakfast, you need to pay them separately though. It’s a great property in a beautiful Location."

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent

"Charming, beautifully decorated, and pet-friendly hotel We enjoyed our stay at this charming hotel. It is very cutely decorated and has lots of character. The location is great if you prefer staying outside the busy city center while still having convenient access to everything. The room was a good size—not too big or too small—with a comfortable bed and a spacious bathroom. Breakfast was also very good, offering everything you need to start the day. Another big plus is that the hotel is pet-friendly! If I had to mention anything, it would be a few minor finishing details, such as the AC vents, that seemed a little unfinished. Nothing major, just small touches that could make the overall experience even better. Overall, a lovely hotel with charm, comfortable rooms, and a welcoming atmosphere. We would happily stay again!"

Il Chiostro del Carmine

8/10 Good

"The location was excellent, within walking distance to all the sights but far enough that it was quiet. Breakfast was excellent and if you can get window seating, it will make a perfect start of the day. The staff was helpful but remains in the background unless you need something. The room was clean, only caveat is the shower is rather small for such a big bathroom. We will stay here again."

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The thermal spa experience is unique in the region and is awsome, especially during the fall season when it is cooler outside. The room was super clean and the staff was very helpful throughout the entire week, and we felt welcomed at any time of day. 15 min by car from Montalcino, strongly recommend to rent a car since it is slightly remote. Overall 9.5/10, strongly recommend for a special occasion."

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 $51 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?

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.

Room 1

Check prices for these dates

Our top choices for Roccastrada vacation rentals

1. Casa Giovy - A family-friendly village nestled among the hills, the sea, and hot springs in the Tuscan Maremma

2. Country House il Ciliegio

3. Giacinto – Classic Double Room

4. Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi

5. Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi

6. Uva Spina – Intimate Double Room with Val di Farma View

7. Deluxe Room 'Narciso Dei Poeti' with Extra Bed

8. Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View

9. Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

10. Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

11. Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi

12. Tuscasì Aparthotel

13. Idolina Guest House

14. Appartamenti La Vecchia Posta

15. Casa di Campagna in Toscana

16. B&B Le Scalette di Piazza

17. Botrona B&B

18. Pineta Azzurra

19. La Dimora di Dida

20. Palazzo Saloni

Find vacation rentals that suit your style

Top Roccastrada Hotel Reviews

L'Orto delle Terme

Hotel Italia

Palazzo Ravizza

Hotel Athena

Villa Ermellina Siena, a Tribute Portfolio Hotel

Il Chiostro del Carmine

Castiglion del Bosco, A Rosewood Hotel

Castello di Velona Resort Thermal SPA & Winery

Grand Hotel Bastiani

Find out more about Roccastrada

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