
Vacation rentals in Montemassi
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Montemassi
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Montemassi vacation rentals
Other great vacation rentals in Montemassi
Guest favorite

Villa in Roccastrada
4.96 out of 5 average rating, 56 reviewsHoliday home with pool in the Tuscan Maremma
Sonja & ChristofRating, 5 stars9 months ago
We had a wonderful holiday in this beautiful accomodation. Thanks a lot

Home in Montemassi
4.91 out of 5 average rating, 11 reviewsMaria's Tower: a Bird's Eye View to the Sea Coast
PeterRating, 5 stars21 months ago
We spent intensive and eventful days in Montemassi and the surrounding area thanks to Gabriella. The spacious, ingeniously renovated and extremely well-furnished apartment is located in the middle of the old core of this beautiful place, offers an ingenious view to the south and into the medieval village. Our son was able to prepare for an exam thanks to the tranquility (car-free alleys). It was very helpful that the apartment is perfectly ventilated thanks to the mountain location and many windows and there is also an air conditioner. Montemassi as a place is enchantingly beautiful, the location is ideal for exploring the entire Maremma. There are very good restaurants in nearby Roccatederighi, the parco naturale della maremma is as close as Vetulonia, Monte Amiata, Monte Argentario, Val di Cornia, ... However, the most outstanding thing is the host. A treasure of communication, hospitality, helpfulness and loving humor. Grazie mille, cara Gabriella 🧡
Guest favorite

Farm stay in Gavorrano
5 out of 5 average rating, 7 reviewsPodere Montauzzo | Farmhouse with pool 16/18 p
MarekRating, 5 stars2 weeks ago
The arrangement with Cristina was perfect—flexible and proactive. She even took the initiative to secure a reservation for us at a local restaurant on the first day, which I really appreciated along with the others. Additionally, any inquiry was answered within an hour. The house, accommodating 18 people including children, remained spacious and well-designed. I particularly valued the large shared terrace, complete with an outdoor kitchen, as well as the pool, which was cleaned daily :). The location and village itself had a fantastic atmosphere.

Condo in Roccatederighi
5 out of 5 average rating, 3 reviewsSunset Cottage in Maremma
AlexRating, 5 stars9 months ago
Brigitte was a great host. Really responsive. Its is in a village with a few bars and restaurants so you get the best of both worlds: outside space and a wonderful view plus you can eat out or have a drink in the village without having to drive at the end of a long day sightseeing. Great place to unwind from the stresses of London! The village is also well placed to explore Tuscany and visit less touristy spots.

Farm stay in Monte San Savino
5 out of 5 average rating, 3 reviewsLuxe Villa,Infinity Pool,Stunning View, Activities
Qingyue Rating, 5 stars2 months ago
Very nice experience!This house is just as good as we imagined.Beautiful scenery, decoration style, and plenty of food.The host was very welcoming and tried to provide the best service.And it's just amazing to enjoy the outdoor pool and sauna at the end of March.
Guest favorite

Condo in Montemassi
4.92 out of 5 average rating, 13 reviewsMontemassi Apartment: Marina's little house
YvonneRating, 5 stars11 months ago
Everything was perfect for me. Thank you!
Top guest favorite

Farm stay in San Quirico d'Orcia
4.98 out of 5 average rating, 44 reviewsWine Loft in the vineyards
HilaryRating, 5 stars2 weeks ago
The Wine Loft is incredibly peaceful and beautiful. The modern architecture is gorgeous and the views are magical. We traveled by trains and it was easy to take a taxi (arranged by the Wine Loft) from the station. Additionally, we enjoyed walking the country path through the woods and meadow to Bagno Vignoni. We highly recommend this beautiful property. The wines were a phenomenal addition to the stay.
Guest favorite

Apartment in La Cetina
4.95 out of 5 average rating, 39 reviewsBrotes Mandorlo Apartment
NastasyaRating, 5 stars3 weeks ago
Our stay at La Cetina was nothing short of idyllic. The villa is quiet and peaceful, exactly what we were after. It was a short drive from near villages, but we were more than happy spending most of our holiday on-site, by the pool, in the hot tub, or using the BBQ. Mariana was the perfect host - super helpful even before our trip started, and right until the end with giving us tips for our trip back (and even gifted us some of their homemade honey). On homemade produce: the wines and olive oil that they offer on site are absolutely delicious. We would definitely go back. Thank you!
Destinations to explore
- Florence Vacation rentals
- Pisa Vacation rentals
- Bologna Vacation rentals
- Rome Vacation rentals
- Portofino Vacation rentals
- Riviera di Levante Vacation rentals
- Genoa Vacation rentals
- Italian Riviera Vacation rentals
- Francavilla al Mare Vacation rentals
- Verona Vacation rentals
- Venice Vacation rentals
- Menton Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Elba
- Giglio Island
- Feniglia
- Gulf of Baratti
- Cala Violina
- Spiaggia di Capo Bianco
- Spiaggia Di Sansone
- Kite Beach Fiumara
- Marina di Grosseto beach
- Spiaggia di Marina Di Campo
- Cavallino Matto
- Avignonesi Winery Fattoria Le Capezzine
- Cala Di Forno
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Zuccale
- Spiaggia Di Barbarossa
- Spiaggia della Padulella
- Spiaggia Marina di Cecina
- Santa Maria della Scala
- Spiaggia di Seccione - Portoferraio (li)
- Cala del Leone
- CavallinoMatto
- Spiaggia di Cavo
- Spiaggia Di Sottobomba