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Montemassi Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Montemassi vacation 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
$85 nightly
The price is $96
Oct 16 - Oct 17
Total with taxes and fees
Country House il Ciliegio
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

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
$80 nightly
The price is $90
Oct 23 - Oct 24
Total with taxes and fees
Agriturismo Benvenuti
A window with a view of a green landscape and a clear sky.

3. 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
$106 nightly
The price is $106
Oct 14 - Oct 15
Total with taxes and fees
Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills
A stone building with outdoor seating and string lights.

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

Uva Spina – Intimate Double Room with Val di Farma View
Piloni
$141 nightly
The price is $141
Oct 13 - Oct 14
Total with taxes and fees
Uva Spina – Intimate Double Room with Val di Farma View
A backyard with a swimming pool, lounge chairs, and a stone pathway.

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

San Michele - Casa Giano: Oak Grove View, Shared Pool & Wi-Fi
Montieri
$148 nightly
The price is $148
Oct 13 - Oct 14
Total with taxes and fees
San Michele - Casa Giano: Oak Grove View, Shared Pool & Wi-Fi
A white building with a solar panel roof, surrounded by green fields and trees.

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

Room 'La Concia - Spiga' with Shared Garden and Wi-Fi
Gavorrano
$96 nightly
The price is $100
Nov 1 - Nov 2
Total with taxes and fees
Room 'La Concia - Spiga' with Shared Garden and Wi-Fi
A person relaxing in a hot tub with a glass of wine.

7. 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
$88 nightly
The price is $96
Oct 14 - Oct 15
Total with taxes and fees
Botrona B&B
A bedroom with a four-poster bed, a nightstand, a bedside table, a vase, a window with curtains, and a ceiling with exposed beams.

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

Panorama-Ferien-Toscana Your vacation home in Tuscany
Massa Marittima
$118 nightly
The price is $118
Oct 13 - Oct 14
Total with taxes and fees
Panorama-Ferien-Toscana Your vacation home in Tuscany
A modern kitchen with a built-in oven, stainless steel appliances, and decorative items on the shelves.

9. Il Bennu

Il Bennu
Gavorrano
$169 nightly
The price is $191
Oct 13 - Oct 14
Total with taxes and fees
Il Bennu
A historic stone building with multiple windows and a tower, situated by a beach with clear blue water.

10. 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
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$192 nightly
The price is $192
Oct 13 - Oct 14
Total with taxes and fees
Villino il Corbezzolo, Tuscany, sea, beach, heated swimming pool,spa, gym kneipp
An outdoor patio with a wooden floor, a covered seating area, and a view of a green landscape.

11. 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
$123 nightly
The price is $126
Oct 13 - Oct 14
Total with taxes and fees
Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning
A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

12. 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.
$132 nightly
The price is $136
Oct 13 - Oct 14
Total with taxes and fees
Detached house with garden a few minutes from the abbey of San Galgano
A stone fountain with a light-up base, surrounded by grass and trees, with a building in the background.

13. 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
$79 nightly
The price is $92
Oct 21 - Oct 22
Total with taxes and fees
B&B Terre di Castiglione già Fattoria Pian di Rocca
A historic building with arched windows and a central emblem.

14. 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.
$156 nightly
The price is $176
Oct 13 - Oct 14
Total with taxes and fees
Palazzo Malfatti - Deluxe Apartment with a View of Piazza Garibaldi
A bedroom with a bed, wooden wardrobe, and wall-mounted light fixture.

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

Fragolina di Bosco – Twin Room with Val di Farma View
Piloni
$126 nightly
The price is $126
Oct 13 - Oct 14
Total with taxes and fees
Fragolina di Bosco – Twin Room with Val di Farma View
A cozy room with stone walls, a fireplace, a television, and a dining area with a table set for two.

16. 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.
$108 nightly
The price is $123
Oct 13 - Oct 14
Total with taxes and fees
Palazzo Malfatti - Standard Studio
A restaurant with wooden beams, arched ceilings, and multiple tables with chairs.

17. Room 'Erbe Aromatiche - Poggio Alla Luna' with Wi-Fi

Room 'Erbe Aromatiche - Poggio Alla Luna' with Wi-Fi
Gerfalco
$122 nightly
The price is $122
Oct 13 - Oct 14
Total with taxes and fees
Room 'Erbe Aromatiche - Poggio Alla Luna' with Wi-Fi
A balcony with potted plants, a white plastic chair, and a view of a town with buildings and a tower.

18. Apartment 'Carmelita' with Balcony and Wi-Fi

Apartment 'Carmelita' with Balcony and Wi-Fi
Massa Marittima
10.0 out of 10, Exceptional, (1 review)
"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
$263 nightly
The price is $266
Oct 13 - Oct 14
Total with taxes and fees
Apartment 'Carmelita' with Balcony and Wi-Fi
A white building with a solar panel roof, surrounded by green fields and trees.

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

Room 'Oliva' with Shared Garden and Wi-Fi
Gavorrano
$96 nightly
The price is $100
Nov 1 - Nov 2
Total with taxes and fees
Room 'Oliva' with Shared Garden and Wi-Fi
A stone building with outdoor seating and string lights.

20. Deluxe Room 'Narciso Dei Poeti' with Extra Bed

Deluxe Room 'Narciso Dei Poeti' with Extra Bed
Piloni
$171 nightly
The price is $171
Oct 13 - Oct 14
Total with taxes and fees
Deluxe Room 'Narciso Dei Poeti' with Extra Bed
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 3 days ago
Grand Hotel Bastiani

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 $32 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.

Explore a world of travel with Expedia

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?

Casa Viale Italia - homely house with direct access to the sandy beach: Visitors like this Montemassi vacation home rental. It is located near the beach and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family.

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 Rocca di Frassinello Winery 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.