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Villas in Montemassi

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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 Montemassi villas

    1. 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.

    2. 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.

    3. 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.

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

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

    5. 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.

    6. 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.

    7. 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.

    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 reviews in Montemassi

    Conti di San Bonifacio Wine Resort

    A balcony with a view of a green landscape and a sunset. There are two lounge chairs and a small table with a glass of wine.

    Historic Farmhouse Casa del Chiodo

    A stone-walled balcony with two wooden chairs and a wicker basket of autumn leaves.

    Agriturismo Giù al Pozzo

    An outdoor patio with wooden tables and chairs, large windows offering a view of a mountainous landscape.

    Casale San Galgano

    A pathway leading to a stone building with multiple windows and a covered area on the left.

    Montebelli Agriturismo & Country Hotel

    An aerial view of a property with a swimming pool, manicured lawns, and a variety of trees.

    Relais Le Macine di Stigliano

    A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.

    Antico Casale L'Impostino

    A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.

    Castiglion del Bosco, A Rosewood Hotel

    A pool area with lounge chairs and umbrellas, surrounded by landscaped greenery and a view of a hilltop building.

    Il Pelagone Hotel & Golf Resort Toscana

    A large, multi-story residential building with multiple balconies, surrounded by well-maintained lawns and trees.

    Agriturismo Sweet Cottage

    A swimming pool with lounge chairs, a wooden deck, and a vineyard in the background.

    Mercure Petriolo Siena Terme Spa Hotel

    A pool with lounge chairs and a sunset view.

    Sleep

    An outdoor patio with a patterned floor, a brick wall, and a seating area with chairs and a table.

    Castello Di Vicarello

    An infinity pool with lounge chairs and umbrellas, overlooking a mountainous landscape.

    Frequently Asked Questions

    How much do villas in Montemassi cost?

    You'll pay between $322 and $3,341 per night for a villa in Montemassi. Whatever your budget, the perfect getaway is only a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

    How many villas are there in Montemassi?

    Use up your vacation days and pick from villas in Montemassi. For a family adventure, a getaway with your besties and everything in between, Expedia can help you find the perfect place in just a few clicks.

    Why book your villa in Montemassi with Expedia?

    Reserving a villa in Montemassi is as easy as working out your travel dates and picking the option that meets your requirements. Searching for something inexpensive or upscale, or a property that also comes with a pool? Use Expedia's search filters to narrow your results and find your ideal match.

    How can I find cheap villas in Montemassi?

    The simplest way to score cheap villas in Montemassi is with Expedia's useful filter tool. Tailor your search results by budget, amenities and star rating to find unbeatable deals in only a couple of clicks.

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