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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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 all the way to the sea, in the Tuscan hills

Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills
Roccastrada
$117 nightly
The price is $117
Oct 5 - Oct 6
Total with taxes and fees
Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills
A serene pool area with lounge chairs and a clear view of the sunset over a hilly landscape.

2. Equipped glamping tent and infinity pool in a Tuscan olive grove

Equipped glamping tent and infinity pool in a Tuscan olive grove
Roccastrada
$172 nightly
The price is $172
Sep 25 - Sep 26
Total with taxes and fees
Equipped glamping tent and infinity pool in a Tuscan olive grove
A swimming pool with clear water, surrounded by olive trees and a view of distant mountains.

3. Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun

Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun
Toscana
$190 nightly
The price is $190
Sep 25 - Sep 26
Total with taxes and fees
Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun
A tent with a bed, wooden railings, and a view of trees and mountains.

4. Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove

Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove
Toscana
$159 nightly
The price is $159
Sep 27 - Sep 28
Total with taxes and fees
Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove
A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

5. 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
$79 nightly
The price is $89
Oct 23 - Oct 24
Total with taxes and fees
Country House il Ciliegio
A stone building with outdoor seating and string lights.

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

Uva Spina – Intimate Double Room with Val di Farma View
Piloni
$143 nightly
The price is $143
Sep 28 - Sep 29
Total with taxes and fees
Uva Spina – Intimate Double Room with Val di Farma View
A house with a patio, a table with chairs, and a large umbrella.

7. Casetta di campagna indipendente

Casetta di campagna indipendente
Roccastrada
$430 nightly
The price is $430
Sep 27 - Sep 28
Total with taxes and fees
Casetta di campagna indipendente
A stone building with a tree in front, outdoor seating with tables and chairs, and a paved walkway.

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

Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
Roccastrada
$6,780 nightly
The price is $6,780
Oct 1 - Oct 2
Total with taxes and fees
Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
A swimming pool with clear water, surrounded by olive trees and a view of distant mountains.

9. Stargazer – Your Sky‑View Hideaway in the Tuscan Hills

Stargazer – Your Sky‑View Hideaway in the Tuscan Hills
Toskana
$179 nightly
The price is $179
Sep 25 - Sep 26
Total with taxes and fees
Stargazer – Your Sky‑View Hideaway in the Tuscan Hills
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

10. 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
$81 nightly
The price is $92
Oct 23 - Oct 24
Total with taxes and fees
Agriturismo Benvenuti
A grassy outdoor area with a stone wall and a stone bench.

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

Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
Roccastrada GR
$1,512 nightly
The price is $1,517
Oct 1 - Oct 2
Total with taxes and fees
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
A stone wall with a wooden door, a bell, and a sign.

12. 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
$908 nightly
The price is $908
Sep 25 - Sep 26
Total with taxes and fees
Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi
An outdoor dining area with stone walls, tables, and chairs.

13. 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
$190 nightly
The price is $190
Sep 28 - Sep 29
Total with taxes and fees
Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View
An outdoor dining area with stone walls, tables, and chairs.

14. Fragolina di Bosco – Twin Room with Val di Farma View

Fragolina di Bosco – Twin Room with Val di Farma View
Piloni
$128 nightly
The price is $128
Oct 6 - Oct 7
Total with taxes and fees
Fragolina di Bosco – Twin Room with Val di Farma View
A stone building with outdoor seating and string lights.

15. Narciso dei Poeti – Deluxe Double Room with Extra Bed

Narciso dei Poeti – Deluxe Double Room with Extra Bed
Piloni
$174 nightly
The price is $174
Oct 5 - Oct 6
Total with taxes and fees
Narciso dei Poeti – Deluxe Double Room with Extra Bed
A stone building with a tree in front, outdoor seating with tables and chairs, and a paved walkway.

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

Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
$1,512 nightly
The price is $1,517
Oct 1 - Oct 2
Total with taxes and fees
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
A stone building with a tree in front, outdoor seating with tables and chairs, and a paved walkway.

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

Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
$1,512 nightly
The price is $1,517
Oct 1 - Oct 2
Total with taxes and fees
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
A stone building with a tree in front, outdoor seating, and a lamp post.

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

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
$1,512 nightly
The price is $1,517
Oct 1 - Oct 2
Total with taxes and fees
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

19. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (8 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
$127 nightly
The price is $143
Oct 25 - Oct 26
Total with taxes and fees
Residence Arianna
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

20. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (18 reviews)
"We absolutely loved staying here - the location was very central in Tuscany, it was a beautiful property with a lovely view and a very nice pool area. The staff was amazing and the value was incredible. We would definitely stay here again."
United States
Davide
$132 nightly
The price is $155
Oct 7 - Oct 8
Total with taxes and fees
Corte Francigena - Apartments
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
"We had a wonderful stay at Hotel Athena in Siena. The hotel is very nice, with comfortable, well-appointed rooms and an excellent central location that makes exploring Siena very convenient. The breakfast was exceptional, with a great selection and excellent quality. The staff was consistently friendly, welcoming, and helpful. Overall, a very enjoyable stay, and we would definitely recommend Hotel Athena to anyone visiting Siena."
kenneth 2-night trip
Posted 5 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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Roccastrada in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $34 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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 79 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.