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A historic cathedral with a rainbow, surrounded by traditional buildings.

Siena Vacation Rentals

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    Check prices for these dates

    Check prices for these dates, December 13–14, 2026

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    Our top choices for Siena vacation homes

    1. IL TOLOMEI - new apartment in the middle of the main street

    A stone building with a sign reading "VIA DI CALZOLERIA".

    2. CASA ILARIA - Bright apartment with a view in the historic center

    A room with a large window, a view of a balcony with outdoor furniture, and a kitchen area with a sink.

    3. A cozy, Tuscan-style apartment perfect for families. Pets Allowed

    A rustic building with a brick facade, a small arched window, and a door.

    4. Siena Love Nest: Romantic Suite with Spa & Jacuzzi

    A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

    5. Ebbio – Villa and Organic Farm in Monteriggioni

    A rustic villa with a garden, a pond, and a mountainous backdrop.

    6. Agriturismo La Ferrozzola

    A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

    7. A peaceful spot with a garden between Chianti and Crete, near the old town

    A building with a stone facade, a door, a window, and a patio area with chairs and a table.

    8. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

    An open doorway leading to an outdoor area with a bench, a television on a cabinet, and a framed picture on the wall.

    9. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

    A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

    10. Casa Vacanze Le Case

    A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

    11. Exclusive Stone Tower.

    A stone building with two windows, one with green shutters, and a rose bush in the foreground.

    12. A Nest with a View - A Romantic Getaway Within the City Walls

    A balcony with a view of a stone building and surrounding landscape.

    13. Apartment in Chianti With Pool ID 513

    A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

    14. Detached house with a garden, just a few minutes from the Abbey of San Galgano

    A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

    15. Chianti Craft House Badia a Passignano

    A view through a wooden door of a courtyard with stone walls and potted plants.

    16. Casa Marisa in Castellina in Chianti

    A brick building with a garden, a metal fence, and a clear sky.

    17. Vacation in Poggettone

    A small brick structure with an arched entrance, surrounded by gravel, potted plants, and trees.

    18. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

    A narrow stone staircase leading to a door with a glass panel, flanked by brick walls and metal railings.

    19. Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

    A two-story house with a stone foundation, wooden shutters, and a covered porch with outdoor furniture.

    20. Comfortable double room with a bathroom in the historic center of San Gimignano.

    A bedroom with a bed, a bedside table with a book, a nightstand, and three framed pictures on the wall.

    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 Siena

    Medieval brick buildings circle the shell-shaped Piazza del Campo where the thrilling Palio horse race happens twice each summer. Climb the Torre del Mangia for sweeping views, then explore the zebra-striped Duomo where even the marble floor tells fascinating stories.

    See all hotels in Siena

    A historic cathedral with a rainbow, surrounded by traditional buildings.

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