Montemassi Vacation Rentals

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Our top choices for Montemassi vacation rentals

Fattoria Pian di Rocca

Fattoria Pian di Rocca
Castiglione della Pescaia
9.6 out of 10, Exceptional, (30)
"Great place to stay. Very clean, close to town, great breakfast. "
Canada
Jose Pedro
$61 nightly
The price is $68
Jan 11 - Jan 12, 2026
Total with taxes and fees
Fattoria Pian di Rocca

Casa in Maremma Tuscany Village

Casa in Maremma Tuscany Village
3.0 star property
Scarlino
8.6 out of 10, Excellent, (76)
"Für Hundehalter sehr empfehlenswert"
Switzerland
Johnny
Casa in Maremma Tuscany Village

Two-room apartment in residence with swimming pool and restaurant

Two-room apartment in residence with swimming pool and restaurant
Grosseto
8.0 out of 10, Very Good, (1)
"Tutto ok"
Italy
PAOLO T.
$93 nightly
The price is $100
Dec 28 - Dec 29
Total with taxes and fees
Two-room apartment in residence with swimming pool and restaurant

Residence Il Boschetto

Residence Il Boschetto
Grosseto
9.0 out of 10, Wonderful, (6)
"The house is gorgeous! The area is very nice and the amenities were great! "
United States
Enrique
$91 nightly
The price is $101
Jan 12 - Jan 13, 2026
Total with taxes and fees
Residence Il Boschetto

Domus Socolatae Residenza d'Epoca Charming B&B

Domus Socolatae Residenza d'Epoca Charming B&B
Follonica
9.4 out of 10, Exceptional, (23)
"Our stay was amazing, will be back soon!"
United States
Tiffany
Domus Socolatae Residenza d'Epoca Charming B&B

Guest House All'83

Guest House All'83
Grosseto
9.6 out of 10, Exceptional, (5)
"Tutto ok!! Nessuna pecca!!"
Italy
Alessio
Guest House All'83

Comfort, relaxation and nature

Comfort, relaxation and nature
Monticiano
10.0 out of 10, Exceptional, (1)
"Appartamento perfetto non manca nulla e proprietari accoglienti, e gentilissimi. Da tornare"
Italy
Sandra V.
$118 nightly
The price is $120
Jan 2 - Jan 3, 2026
Total with taxes and fees
Comfort, relaxation and nature

Oasis La Rosa in the Countryside

Oasis La Rosa in the Countryside
Follonica
$110 nightly
The price is $116
Jan 2 - Jan 3, 2026
Total with taxes and fees
Oasis La Rosa in the Countryside

Four-room apartment with 3 double bedrooms and 2 bathrooms

Four-room apartment with 3 double bedrooms and 2 bathrooms
Grosseto
10.0 out of 10, Exceptional, (1)
$182 nightly
The price is $197
Dec 29 - Dec 30
Total with taxes and fees
Four-room apartment with 3 double bedrooms and 2 bathrooms

Oasis La Verde in the Countryside

Oasis La Verde in the Countryside
Follonica
$110 nightly
The price is $116
Jan 6 - Jan 7, 2026
Total with taxes and fees
Oasis La Verde in the Countryside

Marconi 1935 B&B and Holiday Home

Marconi 1935 B&B and Holiday Home
Follonica
9.4 out of 10, Exceptional, (9)
"Brilliant little apartment, lovely roof terrace with whirlpool. Easy walk to station and beach. Check in all done via WhatsApp and seamless, beds comfy bathroom.excellent. highly reccomend"
United Kingdom
Mark
Marconi 1935 B&B and Holiday Home

La Fonte di Vivalda

La Fonte di Vivalda
Suvereto
7.0 out of 10, Good, (2)
"tutto molto bello"
Italy
Andrea
La Fonte di Vivalda

Apartment 'Carmelita' with Balcony and Wi-Fi

Apartment 'Carmelita' with Balcony and Wi-Fi
Massa Marittima
10.0 out of 10, Exceptional, (1)
"Pros: Il mio soggiorno presso la casa Carmelita è stato a dir poco spettacolare. Il design elegante , combinato con i suoi servizi di alto livello, ha reso l'esperienza davvero rilassante e piacevole. La titolare è attenta e cortese ha soddisfatto ogni mia esigenza, assicurando che il mio soggiorno fosse il più confortevole possibile. Grazie alla sua posizione comoda e al servizio eccellente, la casa vacanza Carmelita sarà la mia scelta preferita per l'alloggio ogni volta che mi reco a Massa...
Italy
Anonymous traveler
$158 nightly
The price is $160
Jan 8 - Jan 9, 2026
Total with taxes and fees
Apartment 'Carmelita' with Balcony and Wi-Fi

Room 'Casa Del Chiodo - Fragolina di Bosco' with Mountain View, Shared Terrace and Wi-Fi

Room 'Casa Del Chiodo - Fragolina di Bosco' with Mountain View, Shared Terrace and Wi-Fi
Piloni
$106 nightly
The price is $106
Jan 7 - Jan 8, 2026
Total with taxes and fees
Room 'Casa Del Chiodo - Fragolina di Bosco' with Mountain View, Shared Terrace and Wi-Fi

Room 'Camera 1 - Campo Ruffaldo' with Shared Pool, Wi-Fi and Air Conditioning

Room 'Camera 1 - Campo Ruffaldo' with Shared Pool, Wi-Fi and Air Conditioning
Massa Marittima
$121 nightly
The price is $125
Jan 7 - Jan 8, 2026
Total with taxes and fees
Room 'Camera 1 - Campo Ruffaldo' with Shared Pool, Wi-Fi and Air Conditioning

Casa Giovy - Relaxation with a view of the Tuscan hills

Casa Giovy - Relaxation with a view of the Tuscan hills
roccastrada
$162 nightly
The price is $162
Jan 2 - Jan 3, 2026
Total with taxes and fees
Casa Giovy - Relaxation with a view of the Tuscan hills

Apartment 'Montecristo Sei' with Sea View, Wi-Fi and Air Conditioning

Apartment 'Montecristo Sei' with Sea View, Wi-Fi and Air Conditioning
Follonica
$244 nightly
The price is $246
Jan 8 - Jan 9, 2026
Total with taxes and fees
Apartment 'Montecristo Sei' with Sea View, Wi-Fi and Air Conditioning

Apartment 'Di Rosella' with Wi-Fi

Apartment 'Di Rosella' with Wi-Fi
Gavorrano
$116 nightly
The price is $120
Dec 28 - Dec 29
Total with taxes and fees
Apartment 'Di Rosella' with Wi-Fi

Detached house with garden a few minutes from the abbey of San Galgano

Detached house with garden a few minutes from the abbey of San Galgano
Toscana
$139 nightly
The price is $142
Dec 28 - Dec 29
Total with taxes and fees
Detached house with garden a few minutes from the abbey of San Galgano

Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.8 out of 10, Exceptional, (7)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
United States
Michael G.
$168 nightly
The price is $170
Jan 4 - Jan 5, 2026
Total with taxes and fees
Exclusive Stone Tower.
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 Montemassi Hotel Reviews

Find out more about Montemassi

Everything you need to know about Montemassi vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montemassi vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montemassi vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montemassi vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montemassi. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montemassi in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montemassi rentals

At Expedia, we put the best Montemassi vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montemassi rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montemassi vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montemassi. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Montemassi?

Yes, we give you a choice of vacation rentals near popular local attractions in Montemassi, or you can select a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Montemassi?

Private House with Exclusive Swimming Pool Heated and Amazing View: You might want to consider this vacation home rental near Montemassi, which is located in a rural location and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Montemassi?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Montemassi stay.

What’s there to see and do in Montemassi?

While exploring the area, visit family-friendly sights like Piscina Il Giunco, or get outside and enjoy nature at Lago dell'Accesa. Podere Ristella Vineyards and Winery and I Canaloni del Torrente Farma are a couple of places you'll find in the larger area.

What’s a vacation rental in Montemassi like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Montemassi. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.