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Montemassi Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Montemassi holiday rentals

A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

1. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is HK$717
HK$807 total
includes taxes & fees
28 Oct - 29 Oct
Country House il Ciliegio
An outdoor dining area with a table set for two, overlooking a lush green landscape and a hill in the distance.

2. Podere Cascatelle & Agriletizia

Podere Cascatelle & Agriletizia
Massa Marittima
10.0 out of 10, Exceptional, (3 reviews)
"Great for families, convenient parking and facilities, very tranquil."
United States
Ciarán
The price is HK$435
HK$541 total
includes taxes & fees
30 Sept - 1 Oct
Podere Cascatelle & Agriletizia
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

3. Agriturismo Benvenuti

Agriturismo Benvenuti
Roccastrada
6.0 out of 10, (3 reviews)
"La stanza era molto grande e tranquilla. C'è anche un giardino abbastanza ampio a disposizione esclusiva di ogni camera/appartamento. Estrema cortesia. Ovviamente si è in aperta campagna, non in vicinanza del mare o dentro un borgo, ma in auto si raggiungo facilmente molte località interessanti del luogo. Su alcuni particolari, potrebbe essere tenuto un po' meglio, ma nel complesso ha un ottimo rapporto qualità/prezzo per la zona."
Italy
Ivano
The price is HK$556
HK$718 total
includes taxes & fees
23 Oct - 24 Oct
Agriturismo Benvenuti
A swimming pool with clear water, surrounded by olive trees and a view of distant mountains.

4. Stargazer – Your Sky‑View Hideaway in the Tuscan Hills

Stargazer – Your Sky‑View Hideaway in the Tuscan Hills
Toskana
The price is HK$1,166
HK$1,461 total
includes taxes & fees
29 Sept - 30 Sept
Stargazer – Your Sky‑View Hideaway in the Tuscan Hills
A serene pool area with lounge chairs and a clear view of the sunset over a hilly landscape.

5. Equipped glamping tent and infinity pool in a Tuscan olive grove

Equipped glamping tent and infinity pool in a Tuscan olive grove
Roccastrada
The price is HK$1,045
HK$1,340 total
includes taxes & fees
29 Sept - 30 Sept
Equipped glamping tent and infinity pool in a Tuscan olive grove
A window with a view of a green landscape and a clear sky.

6. Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills

Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills
Roccastrada
The price is HK$684
HK$844 total
includes taxes & fees
5 Oct - 6 Oct
Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills
A tent with a bed, wooden railings, and a view of trees and mountains.

7. Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove

Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove
Toscana
The price is HK$1,086
HK$1,246 total
includes taxes & fees
29 Sept - 30 Sept
Ottagono – Your Elegant Nature Retreat in the Tuscan Olive Grove
A swimming pool with clear water, surrounded by olive trees and a view of distant mountains.

8. Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun

Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun
Toscana
The price is HK$1,166
HK$1,461 total
includes taxes & fees
29 Sept - 30 Sept
Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun
A white building with a solar panel roof, surrounded by green fields and trees.

9. Room 'Oliva' with Shared Garden and Wi-Fi

Room 'Oliva' with Shared Garden and Wi-Fi
Gavorrano
The price is HK$883
HK$918 total
includes taxes & fees
29 Sept - 30 Sept
Room 'Oliva' with Shared Garden and Wi-Fi
A backyard with a swimming pool, lounge chairs, and a stone pathway.

10. San Michele - Casa Giano: Oak Grove View, Shared Pool & Wi-Fi

San Michele - Casa Giano: Oak Grove View, Shared Pool & Wi-Fi
Montieri
The price is HK$894
HK$894 total
includes taxes & fees
5 Oct - 6 Oct
San Michele - Casa Giano: Oak Grove View, Shared Pool & Wi-Fi
A patio with a round table and chairs, a window with blinds, and a view of trees and hills.

11. Panorama-Ferien-Toscana Your vacation home in Tuscany

Panorama-Ferien-Toscana Your vacation home in Tuscany
Massa Marittima
10.0 out of 10, Exceptional, (3 reviews)
"Ottima accoglienza, appartamento e giardino come da presentazione Francesco molto gentile e disponibile"
Italy
stefano f.
The price is HK$840
HK$1,197 total
includes taxes & fees
12 Oct - 13 Oct
Panorama-Ferien-Toscana Your vacation home in Tuscany
An outdoor dining area with stone walls, tables, and chairs.

12. Fragolina di Bosco – Twin Room with Val di Farma View

Fragolina di Bosco – Twin Room with Val di Farma View
Piloni
The price is HK$1,005
HK$1,005 total
includes taxes & fees
5 Oct - 6 Oct
Fragolina di Bosco – Twin Room with Val di Farma View
A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

13. 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
10.0 out of 10, Exceptional, (1 review)
"Petite maison cosy et juste parfaite pour deux personnes. La localisation est très bonne, à l’entrée du village de Monticiano. L’accueil a été enthousiaste et la communication très fluide. Merci pour ce beau séjour ! On recommande !"
United States
Julie M.
The price is HK$447
HK$1,081 total
includes taxes & fees
29 Sept - 30 Sept
Detached house with garden a few minutes from the abbey of San Galgano
A bedroom with a four-poster bed, a nightstand, a bedside table, a vase, a window with curtains, and a ceiling with exposed beams.

14. Panorama-Ferien-Toscana Your vacation home in Tuscany

Panorama-Ferien-Toscana Your vacation home in Tuscany
Massa Marittima
Panorama-Ferien-Toscana Your vacation home in Tuscany
An outdoor patio with a wooden floor, a covered seating area, and a view of a green landscape.

15. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning
Braccagni
The price is HK$981
HK$1,008 total
includes taxes & fees
1 Oct - 2 Oct
Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning
A dining area with a stone wall, wooden ceiling beams, a brick fireplace, and a table with fruit.

16. A detached apartment awaits you

A detached apartment awaits you
Toscana
10.0 out of 10, Exceptional, (1 review)
"Wir haben uns sehr wohl gefühlt "
Austria
elke K.
The price is HK$1,171
HK$1,529 total
includes taxes & fees
30 Sept - 1 Oct
A detached apartment awaits you
A cozy room with stone walls, a fireplace, a television, and a dining area with a table set for two.

17. Palazzo Malfatti- Studio flat standard

Palazzo Malfatti- Studio flat standard
Massa Marittima
9.0 out of 10, Wonderful, (2 reviews)
"Short walk to the San Cerbone cathedral and the piazza. Great restaurants and shops very close."
United States
John H.
The price is HK$863
HK$985 total
includes taxes & fees
1 Oct - 2 Oct
Palazzo Malfatti- Studio flat standard
A tree with a swing chair, a clear sky, and a distant tree.

18. Room 'Ghianda' with Shared Garden, Balcony and Wi-Fi

Room 'Ghianda' with Shared Garden, Balcony and Wi-Fi
Gavorrano
10.0 out of 10, Exceptional, (1 review)
"Pros: I proprietari sono splendidamente amichevoli ed accoglienti! La colazione ottima con torte fatte in casa, marmellata di fichi dell'albero in giardino, cornetti freschi e un po' di opzioni salate."
Italy
Anonymous traveller
The price is HK$785
HK$820 total
includes taxes & fees
1 Oct - 2 Oct
Room 'Ghianda' with Shared Garden, Balcony and Wi-Fi
A stone wall with a wooden door, a bell, and a sign.

19. Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi

Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi
Roccastrada
The price is HK$6,796
HK$7,123 total
includes taxes & fees
29 Sept - 30 Sept
Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi
A white building with a solar panel roof, surrounded by green fields and trees.

20. Room 'La Concia - Spiga' with Shared Garden and Wi-Fi

Room 'La Concia - Spiga' with Shared Garden and Wi-Fi
Gavorrano
The price is HK$785
HK$820 total
includes taxes & fees
1 Oct - 2 Oct
Room 'La Concia - Spiga' with Shared Garden and Wi-Fi
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

Grand Hotel Bastiani

Grand Hotel Bastiani

10/10 Excellent
"Great location inside the city walls to explore Grosetto. Lots of great restaurants."
Steven 4-night trip
Posted 5 days ago
Grand Hotel Bastiani

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 holiday rentals in Montemassi?

Yes, there are holiday rentals close to the most popular sights in Montemassi, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Montemassi has to offer?

Casa Viale Italia - homely house with direct access to the sandy beach: This holiday home rental outside of Montemassi is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Montemassi?

With 4 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Montemassi like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montemassi. Holiday rentals feature extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.