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

Holiday Homes in Roccastrada

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 holiday 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 €80
includes taxes & fees
23 Oct - 24 Oct
Agriturismo Benvenuti
A stone building with a tree in front, outdoor seating with tables and chairs, and a paved walkway.

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

Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
Roccastrada
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 €73,232
includes taxes & fees
19 Oct - 20 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 €125
includes taxes & fees
17 Oct - 18 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 €316
includes taxes & fees
17 Oct - 18 Oct
Villa Pianosa, Botri dei Lumachi
An outdoor patio with a wooden floor, a covered seating area, and a view of a green landscape.

6. 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
Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning
A stone building with two windows, one with green shutters, and a rose bush in the foreground.

7. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (10 reviews)
"Loved it!"
United States
Ryan C.
The price is €144
includes taxes & fees
18 Oct - 19 Oct
Exclusive Stone Tower.
A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

8. 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
Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
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 €188
includes taxes & fees
17 Oct - 18 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 €169
includes taxes & fees
18 Oct - 19 Oct
Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
Exterior

11. Villa Giglio, Botri dei Lumachi

Villa Giglio, Botri dei Lumachi
Toscana
The price is €316
includes taxes & fees
17 Oct - 18 Oct
Villa Giglio, Botri dei Lumachi
A pathway leading to a building with stone walls and a tree.

12. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is €128
includes taxes & fees
13 Nov - 14 Nov
A typical Tuscan country house
A stone building with a flat roof, multiple windows, and a small porch area.

13. Podere Cagnesi: Relaxation in nature

Podere Cagnesi: Relaxation in nature
Podere Cagnesi
Podere Cagnesi: Relaxation in nature
Room

14. P.zadelSale Grosseto: Standard Queen Room

P.zadelSale Grosseto: Standard Queen Room
Grosseto
P.zadelSale Grosseto: Standard Queen Room
A balcony with potted plants and a view of rolling hills and mountains.

15. 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 €142
includes taxes & fees
1 Nov - 2 Nov
A Nest with a View - A Romantic Retreat Within the City Walls
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.

16. 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 €240
includes taxes & fees
31 Oct - 1 Nov
Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access
A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

17. Agritourism in Val d'Orcia

Agritourism in Val d'Orcia
montalcino
The price is €334
includes taxes & fees
17 Oct - 18 Oct
Agritourism in Val d'Orcia
A building with a stone facade, a door, a window, and a patio area with chairs and a table.

18. Peaceful corner with garden between Chianti and Crete, very close to Old Town

Peaceful corner with garden between Chianti and Crete, very close to Old Town
Casetta
The price is €102
includes taxes & fees
15 Nov - 16 Nov
Peaceful corner with garden between Chianti and Crete, very close to Old Town
An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

19. 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 €144
includes taxes & fees
20 Oct - 21 Oct
Podere Belsogno-camera Lavanda
A kitchen with a dining table, chairs, a blue bowl, and a radiator.

20. 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 €253
includes taxes & fees
2 Nov - 3 Nov
Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Roccastrada Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Amazing beautiful hotel in historic palace! Love it!"
Chunhua 2-night trip
Posted less than an hour ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Roccastrada

Roccastrada Holiday Homes information

Number of reviews
29
Accommodation
994 Holiday Homes
Lowest Price
€80
Highest Price
€73,232