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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Roccastrada vacation homes

A house with a patio, a table with chairs, and a large umbrella.

1. Casetta di campagna indipendente

Casetta di campagna indipendente
Roccastrada
The price is ￥56,183
￥66,988 total
includes taxes & fees
Oct 9 - Oct 10
Casetta di campagna indipendente
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

2. 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 ￥11,018
￥14,245 total
includes taxes & fees
Oct 23 - Oct 24
Agriturismo Benvenuti
A stone building with a tree in front, outdoor seating with tables and chairs, and a paved walkway.

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

Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
Roccastrada
The price is ￥1,011,788
￥1,055,199 total
includes taxes & fees
Oct 8 - Oct 9
Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
A stone wall with a wooden door, a bell, and a sign.

4. Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi

Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi
Roccastrada
The price is ￥134,773
￥141,256 total
includes taxes & fees
Oct 10 - Oct 11
Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi
A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

5. 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 ￥8,859
￥21,440 total
includes taxes & fees
Oct 8 - Oct 9
Detached house with garden a few minutes from the abbey of San Galgano
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
The price is ￥19,448
￥19,980 total
includes taxes & fees
Oct 8 - Oct 9
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 ￥14,263
￥24,947 total
includes taxes & fees
Oct 8 - Oct 9
Exclusive Stone Tower.
A stone building with a sign reading "Borgo di Mezzo".

8. 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 ￥17,719
￥25,161 total
includes taxes & fees
Oct 20 - Oct 21
The Gelda house, relax with a view
A balcony with potted plants and a view of rolling hills and mountains.

9. 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 ￥25,116
￥25,116 total
includes taxes & fees
Nov 2 - Nov 3
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.

10. 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 ￥37,209
￥42,525 total
includes taxes & fees
Oct 31 - Nov 1
Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access
A stone staircase leading to a building entrance with a sign indicating 'LA NOBILTA DEL TEMPO CASA VACANZA.'

11. 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 ￥39,123
￥44,793 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi
A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

12. 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 ￥16,833
￥20,908 total
includes taxes & fees
Oct 9 - Oct 10
Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included
A narrow stone alley with potted plants and benches.

13. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (77 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is ￥26,578
￥36,146 total
includes taxes & fees
Nov 5 - Nov 6
The House of Alice, charm and relaxation
A stone building with a flat roof, multiple windows, and a small porch area.

14. Podere Cagnesi: Relaxation in nature

Podere Cagnesi: Relaxation in nature
Podere Cagnesi
The price is ￥19,136
￥36,089 total
includes taxes & fees
Oct 14 - Oct 15
Podere Cagnesi: Relaxation in nature
A terrace with a table set for breakfast, overlooking a mountainous landscape.

15. Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace
Castelnuovo dell'Abate
The price is ￥21,263
￥29,060 total
includes taxes & fees
Oct 19 - Oct 20
Il Borghetto - The House of Elba, rooftop panoramic terrace
A pathway leading to a building with stone walls and a tree.

16. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is ￥12,758
￥21,972 total
includes taxes & fees
Nov 5 - Nov 6
A typical Tuscan country house
A beach with clear water, trees, and a distant hill.

17. Villa la Sugherella Tuscany sea, swimming pools spa family golf horse gym kneipp

Villa la Sugherella Tuscany sea, swimming pools spa family golf horse gym kneipp
Gavorrano Toscana
9.6 out of 10, Exceptional, (13 reviews)
"I should say that we travelled a lot in Italy before. But it was either business trips or visiting touristic centers with crowds of tourists, noise, crush, traffic jams and all those things that are so typical for big cities and that we are so seek and tired of! And once our business partner, whose family is from Tuscany, told us that if we want to learn Italy as it is, we should go to Tuscany, as Italy starts from Tuscany! And we decided to go and found via internet absolutely charming place...
United States
Irina S.
The price is ￥31,894
￥36,501 total
includes taxes & fees
Oct 25 - Oct 26
Villa la Sugherella Tuscany sea, swimming pools spa family golf horse gym kneipp
A rustic stone building with a covered patio, outdoor seating, and a garden area.

18. Podere La Speranza – Independent House in Tuscany near San Galgano

Podere La Speranza – Independent House in Tuscany near San Galgano
Chiusdino
The price is ￥88,098
￥102,676 total
includes taxes & fees
Oct 12 - Oct 13
Podere La Speranza – Independent House in Tuscany near San Galgano
Room

19. P.zadelSale Grosseto: Standard Queen Room

P.zadelSale Grosseto: Standard Queen Room
Grosseto
The price is ￥7,973
￥12,934 total
includes taxes & fees
Oct 8 - Oct 9
P.zadelSale Grosseto: Standard Queen Room
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 ￥26,578
￥60,421 total
includes taxes & fees
Oct 10 - Oct 11
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."
JOHN 3-night trip
Posted 20 hours ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Roccastrada

Roccastrada Vacation Homes information

Number of reviews
101
Accommodation
1027 Vacation Homes
Lowest Price
￥12,934
Highest Price
￥1,055,199