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Holiday Rentals in Montemassi

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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 €85
includes taxes & fees
23 Oct - 24 Oct
Country House il Ciliegio
A glass-enclosed structure with a wooden deck, surrounded by various plants and a garden.

2. 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 €80
includes taxes & fees
23 Oct - 24 Oct
Agriturismo Benvenuti
A window with a view of a green landscape and a clear sky.

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

Casa Giovy - Relaxation with a view stretching all the way to the sea, in the Tuscan hills
Roccastrada
Casa Giovy - Relaxation with a view stretching all the way to the sea, in the Tuscan hills
A stone building with a wooden door, green shutters, and two potted plants.

4. Giacinto – Classic Double Room

Giacinto – Classic Double Room
Piloni
The price is €113
includes taxes & fees
2 Nov - 3 Nov
Giacinto – Classic Double Room
A patio with a round table and chairs, a window with blinds, and a view of trees and hills.

5. 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 €108
includes taxes & fees
23 Oct - 24 Oct
Panorama-Ferien-Toscana Your vacation home in Tuscany
A woman sitting at a wooden table under a pergola with a white curtain, surrounded by greenery.

6. Botrona B&B

Botrona B&B
Scarlino
9.4 out of 10, Exceptional, (26 reviews)
"Amazing B&B! Beautiful, clean, and very classy! Staff is excellent and friendly… breakfast is superb and staff’s hospitality is heart warming. Our stay was very pleasant. Home away from home… surprisingly beautiful grounds with jacuzzi and a sauna available whenever you want! Thank you!"
United States
Anna
The price is €94
includes taxes & fees
25 Oct - 26 Oct
Botrona B&B
A white building with a solar panel roof, surrounded by green fields and trees.

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

Room 'La Concia - Spiga' with Shared Garden and Wi-Fi
Gavorrano
Room 'La Concia - Spiga' with Shared Garden and Wi-Fi
314_Il Bennu__7

8. Il Bennu - Breathtaking Views, Panoramic Terrace, and Relaxation in Gavorrano

Il Bennu - Breathtaking Views, Panoramic Terrace, and Relaxation in Gavorrano
Gavorrano
The price is €167
includes taxes & fees
23 Oct - 24 Oct
Il Bennu - Breathtaking Views, Panoramic Terrace, and Relaxation in Gavorrano
A tranquil outdoor pool area with a stone-lined water feature, surrounded by lush greenery and a wooden pergola.

9. Villino il Corbezzolo, Tuscany, sea, beach, heated swimming pool,spa, gym kneipp

Villino il Corbezzolo, Tuscany, sea, beach, heated swimming pool,spa, gym kneipp
Gavorrano Toscana
9.6 out of 10, Exceptional, (13 reviews)
"Last year we have spent our holiday at this beautiful place with our big family. Nice large garden with plenty of flowers, trees, butterflies, small gecos. Quiet place, beautiful views. Nice place for grilling. Supermarket 5 min by car, the beach Follonica cca 15 min by car. We have booked all the villas except the smallest one, so nobody disturbed us. For us one of the best vacations. If possible will come again for sure!!"
United Kingdom
N4Z5dL0p4M4YOjGgLujvG8U2R6jayhLXs+CXI2mhH5hzPz8z6DyPwetl2fEUoYi6GF8RFb+a1xxfKcZRUToFwkdqmIjIeNJLTf2m N.
The price is €188
includes taxes & fees
24 Oct - 25 Oct
Villino il Corbezzolo, Tuscany, sea, beach, heated swimming pool,spa, gym kneipp
A stone patio with a table and chairs, a potted plant, and a door leading to an interior space.

10. Apartment "Casa Le Basse - Giuncarico" with Private Terrace & Wi-Fi

Apartment "Casa Le Basse - Giuncarico" with Private Terrace & Wi-Fi
Gavorrano
The price is €235
includes taxes & fees
24 Oct - 25 Oct
Apartment "Casa Le Basse - Giuncarico" with Private Terrace & Wi-Fi
A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

11. Detached house with a garden, just a few minutes from the Abbey of San Galgano

Detached house with a garden, just 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 €125
includes taxes & fees
23 Oct - 24 Oct
Detached house with a garden, just a few minutes from the Abbey of San Galgano
A cozy room with stone walls, a fireplace, a television, and a dining area with a table set for two.

12. Palazzo Malfatti - Standard Studio

Palazzo Malfatti - Standard Studio
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.
Palazzo Malfatti - Standard Studio
A stone building with multiple windows and a central entrance.

13. Uva Spina – Intimate Double Room with Val di Farma View

Uva Spina – Intimate Double Room with Val di Farma View
Piloni
Uva Spina – Intimate Double Room with Val di Farma View
Property grounds

14. Villa Pianosa, Botri dei Lumachi

Villa Pianosa, Botri dei Lumachi
Toscana
Villa Pianosa, Botri dei Lumachi
Pool

15. Villa Giglio, Botri dei Lumachi

Villa Giglio, Botri dei Lumachi
Toscana
Villa Giglio, Botri dei Lumachi
A balcony with a wooden railing, a view of a forested hillside, and a building with a beige facade and green shutters.

16. Girasole Room – Poggio alla Luna with Mountain View and Wi-Fi

Girasole Room – Poggio alla Luna with Mountain View and Wi-Fi
Gerfalco
Girasole Room – Poggio alla Luna with Mountain View and Wi-Fi
A spacious room with a wooden staircase, a dining area with a table and chairs, a red sofa, and large windows with a view of historical architecture.

17. Palazzo Malfatti - Deluxe Apartment with a View of Piazza Garibaldi

Palazzo Malfatti - Deluxe Apartment with a View of Piazza Garibaldi
Massa Marittima
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed being right in the center of such a lovely town. Enrico was very helpful to us during our stay."
United States
Leslie T.
The price is €157
includes taxes & fees
23 Oct - 24 Oct
Palazzo Malfatti - Deluxe Apartment with a View of Piazza Garibaldi
A stone patio with metal chairs and a table, surrounded by greenery and a stone wall.

18. Holiday Apartment 'Lavanda' with Mountain View, Shared Pool & Wi-Fi

Holiday Apartment 'Lavanda' with Mountain View, Shared Pool & Wi-Fi
Montieri
The price is €156
includes taxes & fees
23 Oct - 24 Oct
Holiday Apartment 'Lavanda' with Mountain View, Shared Pool & Wi-Fi
An outdoor patio with a wooden floor, a covered seating area, and a view of a green landscape.

19. 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 €113
includes taxes & fees
26 Oct - 27 Oct
Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning
A metal table with a tray of food and chairs on a terrace with a view of green hills.

20. B&B Terre di Castiglione già Fattoria Pian di Rocca

B&B Terre di Castiglione già Fattoria Pian di Rocca
Castiglione della Pescaia
9.6 out of 10, Exceptional, (34 reviews)
"We are very happy with everything in this hotel, nice room, comfortable bed, and very good breakfast."
Sweden
Tor
The price is €102
includes taxes & fees
23 Oct - 24 Oct
B&B Terre di Castiglione già Fattoria Pian di Rocca
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 staff, nice breakfast, beautiful building and location."
Peter 3-night trip
Posted 13 days ago
Grand Hotel Bastiani

Find out more about Montemassi

Everything you need to know about Montemassi holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montemassi holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Montemassi holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montemassi holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montemassi holiday rentals we have selected for you start as low as €28 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Montemassi rentals

At Expedia, we put the best Montemassi holiday 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 holiday.

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 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 Rocca di Frassinello Winery 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.