Montemassi Villas Rentals

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Our top choices for Montemassi villas

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

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

Gavorrano

$3,365 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

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

Roccastrada GR

$1,480 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

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

Massa Marittima

$531 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

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

Roccastrada GR

$1,480 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

Roccastrada GR

$1,480 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

Roccastrada GR

$1,480 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

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

Follonica

Anonymous traveler

$319 nightly

Nov 12 - Nov 13

Total with taxes and fees

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Top reviews in Montemassi

A stone building with a wooden door and a circular window.

B&B da Nada Locanda Toscana

Roccastrada

10/10 Excellent

We stayed here for three nights and had an incredible experience. The room was clean, offered a beautiful view, and had reliable Wi-Fi. The location is perfect for exploring, only an hour's drive to Montalcino and incredibly close to several fantastic wineries. The restaurant itself is absolutely fantastic: The panoramic views are amazing, the food is to die for (home cooking style), and the wine selection is excellent. Laura, her husband, and their son, Leonardo, are wonderful, welcoming...

Alexandre

A swimming pool with a view of a valley and mountains.

Valdonica Winery & Vineyard Residence

Roccastrada

10/10 Excellent

Josh

A stone building with multiple windows and a central entrance.

Historic Farmhouse Casa del Chiodo

Roccastrada

10/10 Excellent

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....

Nita Marie

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

Agriturismo Giù al Pozzo

Gavorrano

10/10 Excellent

Micaiah

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.

Conti di San Bonifacio Wine Resort

Gavorrano

10/10 Excellent

Paul

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

Montebelli Agriturismo & Country Hotel

Gavorrano

10/10 Excellent

G&J

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

Antico Casale L'Impostino

Civitella Paganico

10/10 Excellent

Mason

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

Il Pelagone Hotel & Golf Resort Toscana

Gavorrano

10/10 Excellent

Matthew

A pool with lounge chairs and a sunset view.

Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

10/10 Excellent

Anonymous traveler

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

Relais Le Macine di Stigliano

Sovicille

10/10 Excellent

Nicholas

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

Agriturismo Sweet Cottage

Grosseto

10/10 Excellent

The accommodations were very nice and the setting was very peaceful. Although our room had an unusual layout, it had everything we needed. Bedding was excellent. Air conditioning worked perfectly. Breakfast and dinners were wonderful. And the staff were SO friendly and helpful! This is convenient to the marina, Castiglione della Pescaia and central Grosseto. Is a great place to relax by the pool all day, go horseback riding or nearby shopping. We will be back!

John

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

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Excellent

KEDARNATH

A two-story building with a central courtyard, balconies, and a well-maintained garden with pink flowers.

Agriturismo il vecchio imposto

Massa Marittima

10/10 Excellent

Rollie

Frequently Asked Questions

How much do villas in Montemassi cost?

You'll pay between $323 and $3,369 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.

Villas in Montemassi

Bundle & Save

OneKeyCash

Upfront pricing

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Montemassi villas

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

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

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

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

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

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

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

Top reviews in Montemassi

B&B da Nada Locanda Toscana

10/10 Excellent

Frequently Asked Questions

How much do villas in Montemassi cost?

How many villas are there in Montemassi?

Why book your villa in Montemassi with Expedia?

How can I find cheap villas in Montemassi?

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