Montemassi Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Montemassi vacation rentals

Front of property - evening/night
Fattoria Pian di Rocca

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
Fattoria Pian di Rocca
Exterior
Casa in Maremma Tuscany Village

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
Front of property
Domus Socolatae Residenza d'Epoca Charming B&B

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
Interior entrance
Residence Il Boschetto

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
The price is ￥14,358
￥15,794 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Residence Il Boschetto
Junior Studio Suite, 1 Bedroom, Private Bathroom, Tower | Desk, laptop workspace, soundproofing, free WiFi
Guest House All'83

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
Outdoor pool
Two-room apartment in residence with swimming pool and restaurant

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.
The price is ￥11,305
￥15,760 total
includes taxes & fees
Dec 22 - Dec 23
Two-room apartment in residence with swimming pool and restaurant
Outdoor dining
Oasis La Rosa in the Countryside

Oasis La Rosa in the Countryside

Oasis La Rosa in the Countryside
Follonica
The price is ￥9,873
￥18,250 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Oasis La Rosa in the Countryside
Exterior detail
Comfort, relaxation and nature

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.
The price is ￥13,300
￥18,841 total
includes taxes & fees
Dec 23 - Dec 24
Comfort, relaxation and nature
Terrace/patio
Four-room apartment with 3 double bedrooms and 2 bathrooms

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)
The price is ￥23,090
￥31,310 total
includes taxes & fees
Dec 29 - Dec 30
Four-room apartment with 3 double bedrooms and 2 bathrooms
Indoor pool, a heated pool
Private House with Exclusive Swimming Pool Heated and Amazing View

Private House with Exclusive Swimming Pool Heated and Amazing View

Private House with Exclusive Swimming Pool Heated and Amazing View
Boccheggiano
9.6 out of 10, Exceptional, (56)
"Everything was great. The pool was warm. Views are fantastic stretching out to the sea. The town has a good supermarket. Only went to one restaurant, Dell'Upo, but it was good so went back most nights. The hosts were helpful and informative. Planning a return."
United Kingdom
Patrick H.
The price is ￥535,685
￥636,172 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Private House with Exclusive Swimming Pool Heated and Amazing View
Outdoor pool
La Fonte di Vivalda

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
Outdoor dining
Oasis La Verde in the Countryside

Oasis La Verde in the Countryside

Oasis La Verde in the Countryside
Follonica
The price is ￥9,873
￥18,250 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Oasis La Verde in the Countryside
Interior
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

Room 'Casa Del Chiodo - Fragolina di Bosco' with Mountain View, Shared Terrace and Wi-Fi
Piloni
The price is ￥16,699
￥16,699 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Room 'Casa Del Chiodo - Fragolina di Bosco' with Mountain View, Shared Terrace and Wi-Fi
Pool
panoramica casa con piscina privata

panoramica casa con piscina privata

panoramica casa con piscina privata
siena
7.0 out of 10, Good, (10)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
United Kingdom
Olivier B.
panoramica casa con piscina privata
Property grounds
Apartment 'Carmelita' with Balcony and Wi-Fi

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
The price is ￥13,518
￥25,151 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Apartment 'Carmelita' with Balcony and Wi-Fi
Superior Double Room | Minibar, individually furnished, desk, blackout drapes
Marconi 1935 B&B and Holiday Home

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
Pool
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

Room 'Camera 1 - Campo Ruffaldo' with Shared Pool, Wi-Fi and Air Conditioning
Massa Marittima
The price is ￥17,123
￥17,677 total
includes taxes & fees
Dec 22 - Dec 23
Room 'Camera 1 - Campo Ruffaldo' with Shared Pool, Wi-Fi and Air Conditioning
Exterior detail
Exclusive Stone Tower.

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.
The price is ￥15,618
￥26,701 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Exclusive Stone Tower.
Interior
Casa Giovy - Relaxation with a view of the Tuscan hills

Casa Giovy - Relaxation with a view of the Tuscan hills

Casa Giovy - Relaxation with a view of the Tuscan hills
roccastrada
The price is ￥14,630
￥25,344 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Casa Giovy - Relaxation with a view of the Tuscan hills
Poolside bar
Fattoria Maremmana

Fattoria Maremmana

Fattoria Maremmana
4.0 star property
Grosseto
8.0 out of 10, Very Good, (11)
"Staff very friendly and helpful. Very quiet stay as we visited at the beginning of the slow season. "
United States
James
The price is ￥49,194
￥54,113 total
includes taxes & fees
Dec 27 - Dec 28
Fattoria Maremmana
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

Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

10/10 Excellent
"Wonderful stay "
Talib 3-night trip
Posted 1 month ago
Rosewood Castiglion del Bosco

Find out more about Montemassi

Search for holiday rentals in Montemassi on Expedia! You can easily find your home rentals, villas, holiday apartments in Montemassi using one of the methods below:

  • View our selection of featured holiday rentals in Montemassi
  • Use the map to find apartments and other holiday homes in the Montemassi neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Montemassi while they last

Look no further and take a look at our great range of rental properties in Montemassi!

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.