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

Roccastrada Holiday Rentals

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Our top choices for Roccastrada holiday rentals

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
The price is NZ$186
includes taxes & fees
22 Aug - 23 Aug
Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills

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

Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove
Toscana
The price is NZ$274
includes taxes & fees
1 Sept - 2 Sept
Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove

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

Equipped glamping tent and infinity pool in a Tuscan olive grove
Roccastrada
The price is NZ$295
includes taxes & fees
14 Sept - 15 Sept
Equipped glamping tent and infinity pool in a Tuscan olive grove

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

Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun
Toscana
The price is NZ$321
includes taxes & fees
1 Sept - 2 Sept
Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun

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
The price is NZ$189
includes taxes & fees
15 Sept - 16 Sept
Country House il Ciliegio

6. Casetta di campagna indipendente

Casetta di campagna indipendente
Roccastrada
The price is NZ$742
includes taxes & fees
7 Sept - 8 Sept
Casetta di campagna indipendente

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

Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi
Roccastrada
The price is NZ$13,512
includes taxes & fees
31 Aug - 1 Sept
Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi

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

Fragolina di Bosco – Twin Room with Val di Farma View
Piloni
The price is NZ$495
includes taxes & fees
20 Aug - 21 Aug
Fragolina di Bosco – Twin Room with Val di Farma View

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

Stargazer – Your Sky‑View Hideaway in the Tuscan Hills
Toskana
The price is NZ$321
includes taxes & fees
14 Sept - 15 Sept
Stargazer – Your Sky‑View Hideaway in the Tuscan 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 NZ$3,058
includes taxes & fees
31 Aug - 1 Sept
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

11. 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 NZ$1,829
includes taxes & fees
31 Aug - 1 Sept
Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi

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

Uva Spina – Intimate Double Room with Val di Farma View
Piloni
The price is NZ$318
includes taxes & fees
16 Aug - 17 Aug
Uva Spina – Intimate Double Room with Val di Farma View

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

Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
Roccastrada GR
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi

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

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

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

Narciso dei Poeti – Deluxe Double Room with Extra Bed
Piloni
The price is NZ$760
includes taxes & fees
17 Aug - 18 Aug
Narciso dei Poeti – Deluxe Double Room with Extra Bed

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

Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi

17. 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 NZ$816
includes taxes & fees
17 Aug - 18 Aug
Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View

18. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NZ$178
includes taxes & fees
19 Aug - 20 Aug
Tuscasì Aparthotel

19. Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.6 out of 10, Exceptional, (9 reviews)
"Loved it!"
United States
Ryan C.
The price is NZ$323
includes taxes & fees
22 Aug - 23 Aug
Exclusive Stone Tower.

20. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (6 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is NZ$264
includes taxes & fees
12 Sept - 13 Sept
Residence Arianna
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

Find out more about Roccastrada

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Roccastrada holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Roccastrada. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Roccastrada. Seeing all the best attractions is bound to make you fall in love with Roccastrada. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Roccastrada short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Roccastrada?

Yes, there are holiday rentals close to the most popular sights in Roccastrada, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Roccastrada has to offer?

Spacious house between Siena e Firenze with private swimming pool, A/C and Wi-Fi: This holiday home rental outside of Roccastrada is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private balcony, a terrace and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Roccastrada?

Choose from 81 Expedia holiday rentals in Roccastrada for a memorable holiday.

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 holiday rental in Roccastrada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Roccastrada. Holiday rentals provide amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.