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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Roccastrada vacation homes

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

1. 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 AED 256
AED 331 total
includes taxes & fees
23 Oct - 24 Oct
Agriturismo Benvenuti
A compact kitchen with a dining area, a red sofa, and a TV mounted on the wall.

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

Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
Roccastrada
The price is AED 23,571
AED 24,583 total
includes taxes & fees
18 Oct - 19 Oct
Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
A house with a patio, a table with chairs, and a large umbrella.

3. Casetta di campagna indipendente

Casetta di campagna indipendente
Roccastrada
The price is AED 302,041
AED 302,293 total
includes taxes & fees
20 Oct - 21 Oct
Casetta di campagna indipendente
A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

4. Detached house with garden a few minutes from the abbey of San Galgano

Detached house with garden 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 206
AED 499 total
includes taxes & fees
18 Oct - 19 Oct
Detached house with garden a few minutes from the abbey of San Galgano
Property grounds

5. Villa Pianosa, Botri dei Lumachi

Villa Pianosa, Botri dei Lumachi
Toscana
The price is AED 1,108
AED 1,269 total
includes taxes & fees
18 Oct - 19 Oct
Villa Pianosa, Botri dei Lumachi
Exterior

6. Villa Giglio, Botri dei Lumachi

Villa Giglio, Botri dei Lumachi
Toscana
The price is AED 1,294
AED 1,479 total
includes taxes & fees
18 Oct - 19 Oct
Villa Giglio, Botri dei Lumachi
An outdoor patio with a wooden floor, a covered seating area, and a view of a green landscape.

7. 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 452
AED 464 total
includes taxes & fees
18 Oct - 19 Oct
Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning
A bathroom with a sink, toilet, and glass shower enclosure.

8. 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 330
AED 577 total
includes taxes & fees
18 Oct - 19 Oct
Exclusive Stone Tower.
A historic stone building with multiple windows and a tower, situated by a beach with clear blue water.

9. Villino il Corbezzolo, Tuscany, sea, beach, heated swimming pool,spa, gym kneipp

Villino il Corbezzolo, Tuscany, sea, beach, heated swimming pool,spa, gym kneipp
Gavorrano Toscana
9.6 out of 10, Exceptional, (13 reviews)
"Last year we have spent our holiday at this beautiful place with our big family. Nice large garden with plenty of flowers, trees, butterflies, small gecos. Quiet place, beautiful views. Nice place for grilling. Supermarket 5 min by car, the beach Follonica cca 15 min by car. We have booked all the villas except the smallest one, so nobody disturbed us. For us one of the best vacations. If possible will come again for sure!!"
United Kingdom
N4Z5dL0p4M4YOjGgLujvG8U2R6jayhLXs+CXI2mhH5hzPz8z6DyPwetl2fEUoYi6GF8RFb+a1xxfKcZRUToFwkdqmIjIeNJLTf2m N.
The price is AED 660
AED 755 total
includes taxes & fees
18 Oct - 19 Oct
Villino il Corbezzolo, Tuscany, sea, beach, heated swimming pool,spa, gym kneipp
A terrace with a table set for breakfast, overlooking a mountainous landscape.

10. 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
The price is AED 494
AED 675 total
includes taxes & fees
18 Oct - 19 Oct
Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
A balcony with potted plants and a view of rolling hills and mountains.

11. A Nest with a View - A Romantic Retreat Within the City Walls

A Nest with a View - A Romantic Retreat Within the City Walls
Radicondoli
The price is AED 585
AED 585 total
includes taxes & fees
1 Nov - 2 Nov
A Nest with a View - A Romantic Retreat Within the City Walls
A dining area with a stone wall, wooden ceiling beams, a brick fireplace, and a table with fruit.

12. A detached apartment awaits you

A detached apartment awaits you
Toscana
10.0 out of 10, Exceptional, (1 review)
"Wir haben uns sehr wohl gefühlt "
Austria
elke K.
The price is AED 411
AED 576 total
includes taxes & fees
22 Oct - 23 Oct
A detached apartment awaits you
A stone building with a wooden door and two windows with shutters.

13. The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (23 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is AED 619
AED 842 total
includes taxes & fees
3 Nov - 4 Nov
The Casetta di Brunello, quiet and breathtaking views
A stone building with outdoor seating and umbrellas, overlooking a scenic view.

14. Romantic Getaway with Views

Romantic Getaway with Views
Montecastelli Pisano
9.4 out of 10, Exceptional, (35 reviews)
"We loved exploring the nearby forest trails as a family. The clean and comfortable accommodations made our stay enjoyable."
United States
Anonymous traveler
Romantic Getaway with Views
A cozy room with a wooden ceiling, a dining table set with plates, cups, and a vase, and a sofa with a book on it.

15. Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access

Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access
Località Gerfalco Montieri
The price is AED 865
AED 988 total
includes taxes & fees
31 Oct - 1 Nov
Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access
A narrow stone alley with potted plants and benches.

16. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (78 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is AED 619
AED 842 total
includes taxes & fees
1 Nov - 2 Nov
The House of Alice, charm and relaxation
A stone building with a sign reading "Borgo di Mezzo".

17. The Gelda house, relax with a view

The Gelda house, 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 412
AED 585 total
includes taxes & fees
21 Oct - 22 Oct
The Gelda house, relax with a view
A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

18. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
Monteroni d'Arbia
The price is AED 391
AED 486 total
includes taxes & fees
22 Oct - 23 Oct
Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
A kitchen with a dining table, chairs, a blue bowl, and a radiator.

19. 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 911
AED 1,044 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi
A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

20. Agritourism in Val d'Orcia

Agritourism in Val d'Orcia
montalcino
The price is AED 618
AED 1,396 total
includes taxes & fees
18 Oct - 19 Oct
Agritourism in Val d'Orcia
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

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"We had the most amazing stay in this beautiful hotel. Our room was so charming, and the entire hotel felt warm and welcoming in the most Italian way. Breakfast each morning included a beautiful spread of savory and sweet, and croissants that were better than Paris. The terrace sunsets looking over Siena welcomed us each evening after a long day of walking. Location was top notch. Our only “complaint” was that the bed was VERY firm. We will be back!!"
susan 7-night trip
Posted 13 hours ago
Palazzo Ravizza