Roccastrada Villas - Best Villa Roccastrada 2026

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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

3 Nov - 4 Nov

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

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

Roccastrada GR

includes taxes & fees

1 Dec - 2 Dec

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

Roccastrada GR

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

Roccastrada GR

includes taxes & fees

3 Nov - 4 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

3 Nov - 4 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

5 Nov - 6 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

16 Nov - 17 Nov

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

8. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

Siena

Ron M.

A large estate with a swimming pool, tennis court, and multiple guest rooms.

9. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Colle Val D'Elsa

includes taxes & fees

1 Dec - 2 Dec

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

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

Montenero

includes taxes & fees

14 Nov - 15 Nov

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

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

Massa Marittima

includes taxes & fees

3 Nov - 4 Nov

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

12. WPRELAIS BORGO VIGNALUNGA

Toscana

Jeremy F.

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

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

Roccamare

includes taxes & fees

1 Dec - 2 Dec

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

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

Toscana

includes taxes & fees

5 Nov - 6 Nov

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

15. Charming Tuscan villa with a private infinity pool

Castel del Piano

includes taxes & fees

14 Nov - 15 Nov

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

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

Follonica

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Top Roccastrada Hotel Reviews

Palazzo Ravizza

10/10 Excellent

"Convenient location. Beautiful terrace view. Great breakfast"

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."

Hotel Italia

10/10 Excellent

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."

Find out more about Roccastrada

Roccastrada Villas information

Number of reviews	41
Accommodation	542 Villas
Lowest Price	€476
Highest Price	€11,800

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Our top choices for Roccastrada villas

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

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

3. Pet-Friendly Finca Lucente 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 ASCARA - Sixteen Bedroom Villa, Sleeps 31

9. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

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

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

12. WPRELAIS BORGO VIGNALUNGA

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

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

15. Charming Tuscan villa with a private infinity pool

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

Find holiday rentals that suit your style

Top Roccastrada Hotel Reviews

Palazzo Ravizza

Castiglion del Bosco, A Rosewood Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Il Chiostro del Carmine

Hotel Minerva

Hotel Chiusarelli

NH Siena

Castello di Velona Resort Thermal SPA & Winery

Hotel Italia

Find out more about Roccastrada

Roccastrada Villas information

Search Villas in Roccastrada

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 Olivos with Mountain View, Pool, Garden & Wi-Fi

3. Pet-Friendly Finca Lucente 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 ASCARA - Sixteen Bedroom Villa, Sleeps 31

9. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

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

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

12. WPRELAIS BORGO VIGNALUNGA

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

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

15. Charming Tuscan villa with a private infinity pool

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

Find holiday rentals that suit your style

Top Roccastrada Hotel Reviews

Palazzo Ravizza

Find out more about Roccastrada

Roccastrada Villas information