Roccastrada Vacation Rentals

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Our top choices for Roccastrada vacation rentals

Room 'Casa Del Chiodo - Fragolina di Bosco' with Mountain View, Shared Terrace and Wi-Fi

Room 'Casa Del Chiodo - Fragolina di Bosco' with Mountain View, Shared Terrace and Wi-Fi
Piloni
$106 nightly
The price is $106
Jan 7 - Jan 8, 2026
Total with taxes and fees
Room 'Casa Del Chiodo - Fragolina di Bosco' with Mountain View, Shared Terrace and Wi-Fi

Casa Giovy - Relaxation with a view of the Tuscan hills

Casa Giovy - Relaxation with a view of the Tuscan hills
roccastrada
$162 nightly
The price is $162
Jan 2 - Jan 3, 2026
Total with taxes and fees
Casa Giovy - Relaxation with a view of the Tuscan hills

Casetta di campagna indipendente

Casetta di campagna indipendente
Roccastrada
$330 nightly
The price is $330
Dec 28 - Dec 29
Total with taxes and fees
Casetta di campagna indipendente

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
$392 nightly
The price is $392
Jan 6 - Jan 7, 2026
Total with taxes and fees
Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi

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

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
$1,811 nightly
The price is $1,816
Jan 8 - Jan 9, 2026
Total with taxes and fees
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

'Del Chiodo - Mora Selvatica' Room with Mountain View, Shared Terrace and Wi-Fi

'Del Chiodo - Mora Selvatica' Room with Mountain View, Shared Terrace and Wi-Fi
Piloni
$155 nightly
The price is $155
Jan 7 - Jan 8, 2026
Total with taxes and fees
'Del Chiodo - Mora Selvatica' Room with Mountain View, Shared Terrace and Wi-Fi

Room 'Del Chiodo - Giacinto' with Shared Terrace, Garden, and Wi-Fi

Room 'Del Chiodo - Giacinto' with Shared Terrace, Garden, and Wi-Fi
Piloni
$117 nightly
The price is $117
Jan 7 - Jan 8, 2026
Total with taxes and fees
Room 'Del Chiodo - Giacinto' with Shared Terrace, Garden, and Wi-Fi

Room 'Del Chiodo - Narciso Dei Poeti' with Mountain View, Shared Terrace and Wi-Fi

Room 'Del Chiodo - Narciso Dei Poeti' with Mountain View, Shared Terrace and Wi-Fi
Piloni
$143 nightly
The price is $143
Jan 7 - Jan 8, 2026
Total with taxes and fees
Room 'Del Chiodo - Narciso Dei Poeti' with Mountain View, Shared Terrace and Wi-Fi

Room 'Del Chiodo - Uva Spina' with Mountain View, Shared Terrace and Wi-Fi

Room 'Del Chiodo - Uva Spina' with Mountain View, Shared Terrace and Wi-Fi
Piloni
$131 nightly
The price is $131
Jan 7 - Jan 8, 2026
Total with taxes and fees
Room 'Del Chiodo - Uva Spina' with Mountain View, Shared Terrace and Wi-Fi

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

Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi
Roccastrada GR
$1,811 nightly
The price is $1,816
Jan 8 - Jan 9, 2026
Total with taxes and fees
Pet-Friendly Finca 'Flores' with Mountain View, Shared Pool & Wi-Fi

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

Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
$1,811 nightly
The price is $1,816
Jan 8 - Jan 9, 2026
Total with taxes and fees
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

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

Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
$1,811 nightly
The price is $1,816
Jan 8 - Jan 9, 2026
Total with taxes and fees
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi

Piazza Paradiso Accomodation

Piazza Paradiso Accomodation
Siena City Centre
9.2 out of 10, Wonderful, (155)
"What my girlfriend loved the most was the bathtub! We have been busy traveling the last week and a half and she was overjoyed with a chance to soak in a bath tub. Room was spacious and clean, the staff was helpful and friendly. The hotel was centrally located and within easy walking distance to Piazza del Campo. Looking forward to staying with Piazza Paradiso accommodation again. We will definitely recommend Piazza Paradiso to all our friends visiting Siena!"
United States
Niels G.
Piazza Paradiso Accomodation

Fattoria Pian di Rocca

Fattoria Pian di Rocca
Castiglione della Pescaia
9.6 out of 10, Exceptional, (30)
"Great place to stay. Very clean, close to town, great breakfast. "
Canada
Jose Pedro
Fattoria Pian di Rocca

Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8)
"Personal people are very good. "
Switzerland
Wenjuan
$92 nightly
The price is $105
Dec 26 - Dec 27
Total with taxes and fees
Villa le Camelie Siena

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
$88 nightly
The price is $101
Jan 10 - Jan 11, 2026
Total with taxes and fees
Siena Vip

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House

Il Pozzo di Sant'Andrea

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

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
$183 nightly
The price is $207
Dec 27 - Dec 28
Total with taxes and fees
PALAZZO DEL PAPA

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites
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

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 $71 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.

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?

Agriturismo Campo al Crognolo.: This Roccastrada vacation home rental is located in a rural location and has an outdoor pool, a fireplace, and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Roccastrada?

Choose from 63 Expedia vacation rentals in Roccastrada for a memorable vacation.

What’s there to see and do in Roccastrada?

Val di Merse and I Canaloni del Torrente Farma 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.