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

Roccastrada Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Roccastrada vacation rentals

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

1. Casa Giovy - Relaxation with a view stretching all the way to the sea, in the Tuscan hills

Casa Giovy - Relaxation with a view stretching all the way to the sea, in the Tuscan hills
Roccastrada
The price is CA $118
CA $146 total
includes taxes & fees
Oct 31 - Nov 1
Casa Giovy - Relaxation with a view stretching all the way to the sea, in the Tuscan hills
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

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is CA $119
CA $133 total
includes taxes & fees
Nov 2 - Nov 3
Country House il Ciliegio
A stone building with multiple windows and a balcony.

3. Giacinto – Classic Double Room

Giacinto – Classic Double Room
Piloni
The price is CA $176
CA $176 total
includes taxes & fees
Nov 4 - Nov 5
Giacinto – Classic Double Room
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

Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
Roccastrada
The price is CA $8,935
CA $9,318 total
includes taxes & fees
Nov 1 - Nov 2
Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
A vineyard with rows of grapevines, a house with a red roof, and a clear view of distant hills.

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

Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
Roccastrada GR
The price is CA $1,982
CA $2,084 total
includes taxes & fees
Oct 31 - Nov 1
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
A stone building with multiple windows and a balcony.

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

Uva Spina – Intimate Double Room with Val di Farma View
Piloni
The price is CA $197
CA $197 total
includes taxes & fees
Nov 4 - Nov 5
Uva Spina – Intimate Double Room with Val di Farma View
A stone building with multiple windows and a balcony.

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

Deluxe Room 'Narciso Dei Poeti' with Extra Bed
Piloni
The price is CA $239
CA $239 total
includes taxes & fees
Nov 4 - Nov 5
Deluxe Room 'Narciso Dei Poeti' with Extra Bed
A stone building with multiple windows and a balcony.

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

Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View
Piloni
The price is CA $260
CA $260 total
includes taxes & fees
Nov 4 - Nov 5
Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View
A vineyard with rows of grapevines, a house with a red roof, and a clear view of distant hills.

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

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is CA $1,982
CA $2,084 total
includes taxes & fees
Oct 31 - Nov 1
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
A vineyard with rows of grapevines, a house with a red roof, and a clear view of distant hills.

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

Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is CA $1,982
CA $2,084 total
includes taxes & fees
Oct 31 - Nov 1
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
A vineyard with rows of grapevines, a house with a red roof, and a clear view of distant hills.

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

Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is CA $1,982
CA $2,084 total
includes taxes & fees
Oct 31 - Nov 1
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

12. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"A truly special place!"
United States
Jaiden
The price is CA $123
CA $148 total
includes taxes & fees
Nov 25 - Nov 26
Idolina Guest House
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

13. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (188 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is CA $125
CA $150 total
includes taxes & fees
Nov 1 - Nov 2
Bosco della Spina
A courtyard with outdoor seating, a building with multiple windows, and a stone wall.

14. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is CA $360
CA $412 total
includes taxes & fees
Nov 29 - Nov 30
Palazzo Saloni
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.

15. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (33 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is CA $87
CA $116 total
includes taxes & fees
Nov 20 - Nov 21
Tuscasì Aparthotel
A stone courtyard with a bench, potted plants, and a building in the background.

16. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is CA $117
CA $133 total
includes taxes & fees
Nov 15 - Nov 16
Casa di Campagna in Toscana
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

17. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (106 reviews)
"We had a great stay in this conveniently located property. The breakfast was good with many options and staff to assist."
Canada
Morris
The price is CA $166
CA $189 total
includes taxes & fees
Nov 2 - Nov 3
B&B Le Scalette di Piazza
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

18. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.6 out of 10, Exceptional, (22 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is CA $159
CA $188 total
includes taxes & fees
Nov 1 - Nov 2
Corte Francigena - Apartments
A pool area with lounge chairs and umbrellas, surrounded by tall cypress trees and a view of distant hills.

19. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (104 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
The price is CA $250
CA $282 total
includes taxes & fees
Nov 24 - Nov 25
Casanova - Panoramic Rooms and Suites
A traditional stone building with a courtyard, a staircase, and potted plants.

20. Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea
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

Hotel Athena

Hotel Athena

10/10 Excellent
"Hotel Athena was a great property in Siena right inside the town walls. Very convenient as we had a rental car and did day trips throughout Tuscany. Breakfast buffet was included and great selection and quality of food. Would definitely stay here again and recommend to others."
Dawn 4-night trip
Posted 3 hours ago
Hotel Athena

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Roccastrada vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Roccastrada vacation rentals we have selected for you start as low as CA $72 per night. Entering your travel dates in the search wizard 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. 

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.