Best Roccastrada Villas: Private & Luxury Villa Accommodations in Roccastrada

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Roccastrada villas

A two-story house with a stone facade, a tiled roof, and a well-maintained lawn.

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

Roccastrada GR

includes taxes & fees

31 Oct - 1 Nov

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

Roccastrada GR

includes taxes & fees

31 Oct - 1 Nov

A house with a stone wall, a large tree, and a patio area with a bench and table.

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

Roccastrada GR

includes taxes & fees

31 Oct - 1 Nov

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

Roccastrada GR

includes taxes & fees

31 Oct - 1 Nov

A stone building with a garden pathway leading to it.

5. VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

Montalcino

includes taxes & fees

31 Oct - 1 Nov

A clear pool with lounge chairs, a wooden deck, and a view of hills in the background.

6. Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning

Gavorrano

includes taxes & fees

12 Nov - 13 Nov

A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

7. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

includes taxes & fees

31 Oct - 1 Nov

A wooden deck with a glass enclosure overlooking a mountainous landscape.

8. Villa Biancospino to Casa Conti di Sotto, private heated hydromassage,sea,spa

Toscana

"It was a very nice vacation at Casa Conti Di Sotto. The VIP area is really private, you only have one neighbour in the other part of the house. The house and garden are well equipped. The main house is located a few meters away from the VIP area. There are all the other things like swimming pool and sauna. The upper part at the sauna has a nice view of the landscape. Vasile was also very nice and helpful."

Matthias W.

includes taxes & fees

1 Nov - 2 Nov

A stone house with a tiled roof, a small porch, and potted plants.

9. Quercetino: Authentic Tuscan country house near Val d'Orcia & hot springs - Sleeps 10

Montenero

includes taxes & fees

3 Nov - 4 Nov

A stone exterior wall, a glass door entrance, and a brick pathway leading to a staircase.

10. Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center

Massa Marittima

includes taxes & fees

1 Nov - 2 Nov

A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

11. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

Siena

Ron M.

includes taxes & fees

31 Oct - 1 Nov

A stone building with multiple rooms, surrounded by lush greenery and trees.

12. WPRELAIS BORGO VIGNALUNGA

Toscana

Jeremy F.

includes taxes & fees

22 Nov - 23 Nov

An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

13. Villa Mami: A Tuscan retreat full of elegance and charm

Toscana

includes taxes & fees

3 Nov - 4 Nov

A stone-walled patio with wicker furniture, a table, and a view of a green landscape.

14. Wp Relais Villa Vignalunga

CASTIGLIONE D'ORCIA (SI)

"If you are using google maps it is a bit hard to find the property... get directions from you phone. You will also want to have a vehicle with high clearance because you will need to go up and down dirt roads. This being said the Villa is amazing! The grounds is beautifully maintained and the layout is amazing. I highly recommend getting a meal prepared by Valentina (in-villa chef). The only thing that left us unhappy was that the dryer was down and we had to go to a laundrymat nearby. Not a...

Betty

includes taxes & fees

2 Nov - 3 Nov

A stone building with balconies, a gravel path, and a tree.

15. Villa "Bouganville - Colleberto" with Sea View, Private Terrace & Wi-Fi

Follonica

Anonymous traveller

includes taxes & fees

1 Nov - 2 Nov

A stone building with a car parked in front, surrounded by trees and a gravel path.

16. Charming Tuscan villa with a private infinity pool

Castel del Piano

includes taxes & fees

3 Nov - 4 Nov

A yellow building with a tiled walkway leading to a door, flanked by two small, colorful lighthouse models.

17. Villa 'Paradiso' with Private Terrace, Private Garden and Wi-Fi

Castiglione della Pescaia

"Pros: *Villa Paradiso, Castiglione della Pescaia* Bij aankomst hartelijk ontvangen door de eigenaar, we konden de auto op het erf zetten om uit te laden. Appartement met grote, lichte keuken aan de buitenzijde, met rondom zon en fraai uitzicht. Unieke, maritieme inrichting met bakboord- en stuurboordtorens - heel charmant. Mooie grote badkamer . We hebben enorm genoten van de beide terrassen met prachtige op- en ondergaande zon. Tip: even vragen om ligstoelen en parasol. Ideale ligging net...

Anonymous traveller

A beachside dining setup with a table set for two, overlooking the ocean.

18. VILLA ALBA CHIARA - Six Bedroom Villa, Sleeps 12

Roccamare

includes taxes & fees

30 Nov - 1 Dec

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Roccastrada Hotel Reviews

Hotel Athena

8/10 Good

"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” port!!"

Il Chiostro del Carmine

10/10 Excellent

"Everything about this place is excellent. We had a wonderful stay and beautiful views of the sunrise! One thing to note is that you do have to take a flight of stairs to your room as there is no elevator. If you have luggage you may want to take this into consideration. We did and it was manageable!"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The thermal spa experience is unique in the region and is awsome, especially during the fall season when it is cooler outside. The room was super clean and the staff was very helpful throughout the entire week, and we felt welcomed at any time of day. 15 min by car from Montalcino, strongly recommend to rent a car since it is slightly remote. Overall 9.5/10, strongly recommend for a special occasion."

Find out more about Roccastrada

Roccastrada Villas information

Number of reviews	105
Accommodation	376 Villas
Lowest Price	AU$460
Highest Price	AU$11,181

Explore a world of travel with Expedia

More ways to book

Book Villas in Roccastrada on Expedia.it

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Roccastrada villas

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

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

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

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

5. VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

6. Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning

7. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

8. Villa Biancospino to Casa Conti di Sotto, private heated hydromassage,sea,spa

9. Quercetino: Authentic Tuscan country house near Val d'Orcia & hot springs - Sleeps 10

10. Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center