Book Holiday Homes in Roccastrada

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Roccastrada

Eco house with pool and fantastic views

Eco house with pool and fantastic views

Scansano
Stay at this vacation home in Scansano. Enjoy free WiFi, private pools, and a water park. Popular attractions Tiaso Bioviticulturists - Cellar and Necropoli ...
Eco house with pool and fantastic views
Independent house in the hills of the Sienese countryside

Independent house in the hills of the Sienese countryside

Siena
Stay at this vacation home in Sovicille. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions San Leonardo al Lago and Church of San Niccolo ...
Independent house in the hills of the Sienese countryside
Beautiful vacation home with annexe, 3 km from Scarlino, in the heart of the Tuscan Maremma.

Beautiful vacation home with annexe, 3 km from Scarlino, in the heart of the Tuscan Maremma.

Scarlino -GR-
Stay at this vacation home in Scarlino. Enjoy a garden, an in-room coffeemaker, and housekeeping. Popular attractions Castello di Scarlino and Il Pupillo are ...
Beautiful vacation home with annexe, 3 km from Scarlino, in the heart of the Tuscan Maremma.
Save an average of 15% on thousands of hotels when you're signed in
Terre di Maremma, Ciclamino Apartment, Tuscany

Terre di Maremma, Ciclamino Apartment, Tuscany

Sticciano
Stay at this vacation home in Roccastrada. Enjoy free breakfast, free WiFi, and private pools. Popular attractions Torre del Belvedere and Church of Saints Stephen ...
Terre di Maremma, Ciclamino Apartment, Tuscany
Beautiful stone house with garden and private pool.

Beautiful stone house with garden and private pool.

Sovicille - Siena
Stay at this vacation home in Siena. Enjoy free WiFi, private pools, and a garden. Popular attractions San Leonardo al Lago and Siena Stadium are located ...
Beautiful stone house with garden and private pool.
Capanna di Elfo by Best of Mas

Capanna di Elfo by Best of Mas

Siena
Stay at this vacation home in Siena. Enjoy a garden, balconies, and air conditioning. Our guests praise the helpful staff in our reviews. Popular attractions ...
Capanna di Elfo by Best of Mas
Seaside house with private garden

Seaside house with private garden

Follonica
Book a stay at this beach vacation home in Follonica. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Church of San Leopoldo and MAGMA ...
Seaside house with private garden
Historic center of Siena: Castellare residence with TV, WI-FI and AIR CONDITION

Historic center of Siena: Castellare residence with TV, WI-FI and AIR CONDITION

Siena
Stay at this vacation home in Siena. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Piazza del Campo and Palazzo Salimbeni are located ...
Historic center of Siena: Castellare residence with TV, WI-FI and AIR CONDITION
Independent apartment in the hills near the sea

Independent apartment in the hills near the sea

Castiglione della Pescaia
Stay at this vacation home in Castiglione della Pescaia. Enjoy free WiFi, a garden, and patios. Popular attractions Natural Reserve Diaccia Botrona and Red House ...
Independent apartment in the hills near the sea
Don't see what you're looking for?
See all available properties in Roccastrada
View all properties
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.

Roccastrada Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Roccastrada vacation homes are the perfect way for you to wing it.

Holiday houses in Roccastrada let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Roccastrada in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Roccastrada adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Roccastrada with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Roccastrada vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Roccastrada Holiday Homes essential information

Accommodation
815 Holiday Homes
Lowest Price
NZ$166
Highest Price
NZ$560
Popular accommodation
Eco house with pool and fantastic views, Independent house in the hills of the Sienese countryside, Beautiful vacation home with annexe, 3 km from Scarlino, in the heart of the Tuscan Maremma., Terre di Maremma, Ciclamino Apartment, Tuscany, Beautiful stone house with garden and private pool., Capanna di Elfo by Best of Mas, Seaside house with private garden, Historic center of Siena: Castellare residence with TV, WI-FI and AIR CONDITION, Independent apartment in the hills near the sea

Top trending hotels in Roccastrada

Terre di Maremma, Ciclamino Apartment, Tuscany

Terre di Maremma, Ciclamino Apartment, Tuscany

Sticciano
Stay at this vacation home in Roccastrada. Enjoy free breakfast, free WiFi, and private pools. Popular attractions Torre del Belvedere and Church of Saints Stephen ...
Terre di Maremma, Ciclamino Apartment, Tuscany
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
The price is NZ$186 per night from 7 Jan to 8 Jan
NZ$186
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this 4-star business-friendly hotel in Siena. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...
Hotel Athena
NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1, Siena, SI
Fully refundableReserve now, pay when you stay
The price is NZ$166 per night from 24 Dec to 25 Dec
NZ$166
includes taxes & fees
24 Dec - 25 Dec
Stay at this 4-star hotel in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
NH Siena
Save an average of 15% on thousands of hotels when you're signed in
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85, Siena, SI
Fully refundableReserve now, pay when you stay
The price is NZ$560 per night from 5 Jan to 6 Jan
NZ$560
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 5-star luxury hotel in Siena. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the room service ...
Grand Hotel Continental Siena – Starhotels Collezione
Don't see what you're looking for?
See all available properties in Roccastrada
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.