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Villas in Montemassi

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

Location: Gavorrano
Price: $3,329 nightly, $3,333 total, Nov 17 - Nov 18, Total with taxes and fees, for Our top choices for Montemassi villas

2. 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.

Location: Massa Marittima
Price: $525 nightly, $525 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Montemassi villas

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

A house with a stone facade, an arched entrance, and a gravel driveway.

Location: Follonica
Guest rating: 10/10 (Exceptional, 1 review)
Price: $316 nightly, $320 total, Nov 17 - Nov 18, Total with taxes and fees, for Our top choices for Montemassi villas
Review: Pros: La vue proximité mer et ville superbe villa vue sur mer, by Anonymous traveler

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.

Location: Gavorrano
Review: Amazing all-around experience. We will be back!, by Paul, July 29, 2024, rated 10/10 Excellent

Historic Farmhouse Casa del Chiodo

A stone building with a wooden door and a small table with a basket of flowers.

Location: Roccastrada
Review: The Casa Del Chiodo was the perfect Tuscan B&B experience for us. From the moment Marco greeted us to the amazing multiple course evening meal that owner/chef Paola prepared to the breakfast served by Irene, it was the epitome of Italian hospitality. While the evening meal was extra, it was definitely worth it as it showcased local farm grown and hunted/gathered foods (such as mushrooms, venison and roasted chestnuts). Our room was clean, true to historical construction with modern amenities...., by Nita Marie, October 29, 2026, rated 10/10 Excellent

Agriturismo Giù al Pozzo

A house with a solar panel roof, a covered patio, and a landscaped garden.

Location: Gavorrano
Review: This stay was beautiful! There was pretty countryside and the hotel grounds were very pretty as well., by Micaiah, March 23, 2026, rated 10/10 Excellent

Casale San Galgano

A stone building with a balcony, a tree in the front yard, and a sunset in the background.

Location: Chiusdino
Review: Staff was great! Made the stay feel like home, by Adam, September 17, 2026, rated 10/10 Excellent

Montebelli Agriturismo & Country Hotel

A house surrounded by lush greenery and a well-maintained lawn.

Location: Gavorrano
Review: If after the hassel and bussel of large cities you require a quiet place to recharge, Montebelli will fulfill this purpose. Located in a beautiful countryside, with two pools and plenty of opportunities for relaxing and hiking, but close enough to the sea and other sights, this is a perfect place to slow down and smell the linden (beautiful trees and fragrance bushes in the premises), by G&J, June 19, 2015, rated 10/10 Excellent

Relais Le Macine di Stigliano

A stone building with a courtyard, surrounded by lush greenery and a hillside.

Location: Sovicille
Review: We truly had an amazing time staying here. the staff was so helpful. The room was absolutely perfect. I would highly recommend if you would like to stay in a piece of heaven. We can't wait to visit again., by Nicholas, November 5, 2026, rated 10/10 Excellent

Antico Casale L'Impostino

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

Location: Civitella Paganico
Review: Monia and Fabio are absolutely delightful hosts! My wife and I were shocked by how kind and accomodating they were - especially with our dietary needs. The food was magnificent, and the vineyard was beautiful! All the staff were attentive and helpful. We would definitely recommend Tenuta L’Impostino to everyone!, by Mason, June 10, 2026, rated 10/10 Excellent

Castiglion del Bosco, A Rosewood Hotel

A stone villa with a swimming pool, surrounded by lush greenery and hills.

Location: Montalcino
Review: Unique property well maintained and quite Serene , great staff, by KEDARNATH, October 30, 2026, rated 10/10 Excellent

Il Pelagone Hotel & Golf Resort Toscana

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

Location: Gavorrano
Review: Bought kids room too and already reviewed., by Matthew, July 25, 2026, rated 10/10 Excellent

Mercure Petriolo Siena Terme Spa Hotel

A pool with a water feature, lounge chairs, and a view of a forested hillside.

Location: Civitella Paganico
Review: unbelievably good everything. only location is not up to par....in the middle of nowhere - far from relevant towns. that said, everything else is a dream., by Anonymous traveler, July 24, 2014, rated 10/10 Excellent

Sleep

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

Location: Follonica
Review: Great location!, by Steven, July 5, 2024, rated 10/10 Excellent

Castello Di Vicarello

A villa with a swimming pool, surrounded by lush greenery and tall cypress trees.

Location: Cinigiano
Review: AMAZING hotel, I cannot stress enough how insanely perfect our whole experience and stay was. Truly something magical and something you have to experience for yourself to understand., by hala, September 21, 2026, rated 10/10 Excellent

Marina di Scarlino Resort

A pool area with lounge chairs and umbrellas, surrounded by a marina with boats.

Location: Scarlino
Review: Mama mía! Where do I begin? The concierge staff were one step ahead of us even before we checked in. Grazie Giulia!!! My fiancée and I could not have asked for more. They food onsite is fantastic and the local options are a brisk walk or a short taxi ride away. We will be coming back!, by Edwin, September 24, 2024, rated 10/10 Excellent

Frequently Asked Questions

How much do villas in Montemassi cost?

You'll pay between $320 and $3,333 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.