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Our top choices for Roccastrada vacation homes

1. P.zadelSale Grosseto: Standard Queen Room

P.zadelSale Grosseto: Standard Queen Room
Grosseto
The price is AED 182
AED 267 total
includes taxes & fees
15 Nov - 16 Nov
P.zadelSale Grosseto: Standard Queen Room

2. Detached house with a garden, just a few minutes from the Abbey of San Galgano

Detached house with a garden, just a few minutes from the Abbey of San Galgano
Toscana
10.0 out of 10, Exceptional, (1 review)
"Petite maison cosy et juste parfaite pour deux personnes. La localisation est très bonne, à l’entrée du village de Monticiano. L’accueil a été enthousiaste et la communication très fluide. Merci pour ce beau séjour ! On recommande !"
United States
Julie M.
The price is AED 202
AED 462 total
includes taxes & fees
15 Nov - 16 Nov
Detached house with a garden, just a few minutes from the Abbey of San Galgano

3. Villa Pianosa, Botri dei Lumachi

Villa Pianosa, Botri dei Lumachi
Toscana
The price is AED 1,090
AED 1,183 total
includes taxes & fees
15 Nov - 16 Nov
Villa Pianosa, Botri dei Lumachi

4. Villa Giglio, Botri dei Lumachi

Villa Giglio, Botri dei Lumachi
Toscana
The price is AED 1,090
AED 1,183 total
includes taxes & fees
15 Nov - 16 Nov
Villa Giglio, Botri dei Lumachi

5. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning
Braccagni
The price is AED 444
AED 457 total
includes taxes & fees
15 Nov - 16 Nov
Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

6. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is AED 324
AED 539 total
includes taxes & fees
15 Nov - 16 Nov
Exclusive Stone Tower.

7. A Casetta di Brunello, tranquil and with breathtaking views.

A Casetta di Brunello, tranquil and with breathtaking views.
Montalcino
9.6 out of 10, Exceptional, (24 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is AED 607
AED 781 total
includes taxes & fees
15 Nov - 16 Nov
A Casetta di Brunello, tranquil and with breathtaking views.

8. Podere Cagnesi: Relaxation in the Heart of Nature

Podere Cagnesi: Relaxation in the Heart of Nature
Podere Cagnesi
The price is AED 437
AED 788 total
includes taxes & fees
15 Nov - 16 Nov
Podere Cagnesi: Relaxation in the Heart of Nature

9. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included
Monteroni d'Arbia
The price is AED 385
AED 449 total
includes taxes & fees
23 Nov - 24 Nov
Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

10. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi
Poggiobrucoli
The price is AED 894
AED 1,024 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

11. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is AED 390
AED 572 total
includes taxes & fees
23 Nov - 24 Nov
A typical Tuscan country house

12. Casa Gelda, relax with a view.

Casa Gelda, relax with a view.
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (15 reviews)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
The price is AED 405
AED 547 total
includes taxes & fees
17 Nov - 18 Nov
Casa Gelda, relax with a view.

13. Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (5 reviews)
"The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!"
Austria
Johannes S.
The price is AED 486
AED 538 total
includes taxes & fees
15 Nov - 16 Nov
Podere Belsogno-camera Lavanda

14. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
Castelnuovo dell'Abate
10.0 out of 10, Exceptional, (1 review)
"Il Borghetto is a renovated house in the little village of Castelnuovo dell'Abate, one of the medieval hilltop villages in the UNESCO world heritage-listed Val D'Orcia. It is charming and the beds are very comfortable, but be prepared to take luggage up a steep street to the front door and then steep stairs to both bedrooms. Each bedroom is on a different floor so there is considerable privacy. The piece de la resistance is the rooftop terrace, with 180 degree panoramic views over the valley and...
Australia
Judith F.
The price is AED 486
AED 628 total
includes taxes & fees
15 Nov - 16 Nov
Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

15. Alice's House, charm and relaxation

Alice's House, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (79 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is AED 607
AED 781 total
includes taxes & fees
15 Nov - 16 Nov
Alice's House, charm and relaxation

16. A Nest with a View - A Romantic Getaway Within the City Walls

A Nest with a View - A Romantic Getaway Within the City Walls
Radicondoli
The price is AED 656
AED 656 total
includes taxes & fees
26 Nov - 27 Nov
A Nest with a View - A Romantic Getaway Within the City Walls

17. A peaceful spot with a garden between Chianti and Crete, near the old town

A peaceful spot with a garden between Chianti and Crete, near the old town
Casetta
The price is AED 292
AED 368 total
includes taxes & fees
15 Nov - 16 Nov
A peaceful spot with a garden between Chianti and Crete, near the old town

18. Romantico monolocale in casale

Romantico monolocale in casale
Rispescia
The price is AED 364
AED 462 total
includes taxes & fees
15 Nov - 16 Nov
Romantico monolocale in casale

19. A cozy, Tuscan-style apartment perfect for families. Pets Allowed

A cozy, Tuscan-style apartment perfect for families. Pets Allowed
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."
United States
Shanti R.
The price is AED 607
AED 688 total
includes taxes & fees
15 Nov - 16 Nov
A cozy, Tuscan-style apartment perfect for families. Pets Allowed

20. Siena Love Nest: Romantic Suite with Spa & Jacuzzi

Siena Love Nest: Romantic Suite with Spa & Jacuzzi
Toscana
The price is AED 401
AED 672 total
includes taxes & fees
16 Nov - 17 Nov
Siena Love Nest: Romantic Suite with Spa & Jacuzzi
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.

Learn more about Roccastrada

Hike through the dramatic rock formations of I Canaloni del Torrente Farma, where natural pools invite summer swimming between towering canyon walls. Medieval history comes alive at Sassoforte Castle, while nearby Podere Ristella offers wine tastings showcasing Tuscan varietals grown on sun-drenched slopes.

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

Top reviews in Roccastrada