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

Search Roccastrada Villa Rentals from CA $447

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    Check prices for these dates

    Check prices for these dates, December 14–15, 2026

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    Our top choices for Roccastrada villas

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

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

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

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

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

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

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

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

    5. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

    A stone building with a garden pathway leading to it.

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

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

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

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

    8. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

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

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

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

    10. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

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

    11. WPRELAIS BORGO VIGNALUNGA

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

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

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

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

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

    14. Wp Relais Villa Vignalunga

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

    15. Charming Tuscan villa with a private infinity pool

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

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

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

    17. Villa Liberty in The Centre - No Ztl

    A dining area with a wooden table, white chairs, and a chandelier.

    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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    Learn more about Roccastrada

    Hike through the dramatic rock formations of I Canaloni del Torrente Farma, where natural pools invite summer swimming between towering canyon walls. Medieval history comes alive at Sassoforte Castle, while nearby Podere Ristella offers wine tastings showcasing Tuscan varietals grown on sun-drenched slopes.

    See all hotels in Roccastrada

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

    Top reviews in Roccastrada

    Mercure Petriolo Siena Terme Spa Hotel

    A pool with lounge chairs and a sunset view.

    Villa del Sole Siena

    A terrace with wicker chairs and a table set for breakfast, overlooking a historic town with terracotta buildings and cypress trees.

    L'Orto delle Terme

    A stone building with a pathway leading to a door, surrounded by trees and illuminated by warm lights.

    Palazzo Ravizza

    A table with breakfast items and a wicker chair, overlooking a scenic landscape.

    Relais Le Macine di Stigliano

    A wooden pathway leading to a table set for a meal, surrounded by lush greenery and flowering plants.

    Idolina Guest House

    A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

    Casa Franci Montalcino

    A hot tub with a view of a historic building and mountains.

    Castello di Leonina Relais

    A table set for dining with a scenic view of rolling hills and distant mountains.

    Hotel Certosa Di Maggiano

    A hotel room with a large bed, a vanity with a mirror, and a green archway.

    Palazzo di Valli

    A two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.