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Montemassi Holiday Rentals

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Our top choices for Montemassi holiday rentals

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 NZ$169
includes taxes & fees
5 Nov - 6 Nov
Country House il Ciliegio

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
Podere Cascatelle & Agriletizia

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 NZ$161
includes taxes & fees
23 Oct - 24 Oct
Agriturismo Benvenuti

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

Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun
Toscana
Sahara – The Spacious Family Glamping Tent Under the Tuscan Sun

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

Stargazer – Your Sky‑View Hideaway in the Tuscan Hills
Toskana
Stargazer – Your Sky‑View Hideaway in the Tuscan Hills

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 NZ$189
includes taxes & fees
6 Oct - 7 Oct
Casa Giovy - Relaxation with a view all the way to the sea, in the Tuscan hills

7. Holiday Home 'San Michele - Capanna Scopi' with Pool & Mountain Views, Wi-Fi, A/C

Holiday Home 'San Michele - Capanna Scopi' with Pool & Mountain Views, Wi-Fi, A/C
Montieri
The price is NZ$281
includes taxes & fees
6 Oct - 7 Oct
Holiday Home 'San Michele - Capanna Scopi' with Pool & Mountain Views, Wi-Fi, A/C

8. 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 NZ$1,598
includes taxes & fees
10 Oct - 11 Oct
Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi

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

Fragolina di Bosco – Twin Room with Val di Farma View
Piloni
The price is NZ$225
includes taxes & fees
6 Oct - 7 Oct
Fragolina di Bosco – Twin Room with Val di Farma View

10. Apartment 'Appartamento Speranza' with Wi-Fi and Air Conditioning

Apartment 'Appartamento Speranza' with Wi-Fi and Air Conditioning
Grosseto
The price is NZ$279
includes taxes & fees
4 Nov - 5 Nov
Apartment 'Appartamento Speranza' with Wi-Fi and Air Conditioning

11. Casetta di campagna indipendente

Casetta di campagna indipendente
Roccastrada
The price is NZ$758
includes taxes & fees
7 Oct - 8 Oct
Casetta di campagna indipendente

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

Room 'La Concia - Spiga' with Shared Garden and Wi-Fi
Gavorrano
The price is NZ$179
includes taxes & fees
1 Nov - 2 Nov
Room 'La Concia - Spiga' with Shared Garden and Wi-Fi

13. Palazzo Malfatti - Appartamento deluxe con vista Piazza Garibaldi

Palazzo Malfatti - Appartamento deluxe con vista 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 NZ$315
includes taxes & fees
6 Oct - 7 Oct
Palazzo Malfatti - Appartamento deluxe con vista Piazza Garibaldi

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

15. 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.
Panorama-Ferien-Toscana Your vacation home in Tuscany

16. Fattoria Pian di Rocca

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 NZ$166
includes taxes & fees
18 Oct - 19 Oct
Fattoria Pian di Rocca

17. San Michele - Casa Rosa: Valley & Mountain Views, Shared Pool, Wi-Fi

San Michele - Casa Rosa: Valley & Mountain Views, Shared Pool, Wi-Fi
Montieri
The price is NZ$281
includes taxes & fees
6 Oct - 7 Oct
San Michele - Casa Rosa: Valley & Mountain Views, Shared Pool, Wi-Fi

18. Holiday Home 'San Michele - La Valle' with Valley & Mountain View, Shared Pool, A/C

Holiday Home 'San Michele - La Valle' with Valley & Mountain View, Shared Pool, A/C
Montieri
The price is NZ$281
includes taxes & fees
6 Oct - 7 Oct
Holiday Home 'San Michele - La Valle' with Valley & Mountain View, Shared Pool, A/C

19. Villa la Sugherella Tuscany sea, swimming pools spa family golf horse gym kneipp

Villa la Sugherella Tuscany sea, swimming pools spa family golf horse gym kneipp
Gavorrano Toscana
9.6 out of 10, Exceptional, (13 reviews)
"I should say that we travelled a lot in Italy before. But it was either business trips or visiting touristic centers with crowds of tourists, noise, crush, traffic jams and all those things that are so typical for big cities and that we are so seek and tired of! And once our business partner, whose family is from Tuscany, told us that if we want to learn Italy as it is, we should go to Tuscany, as Italy starts from Tuscany! And we decided to go and found via internet absolutely charming place...
United States
Irina S.
The price is NZ$401
includes taxes & fees
26 Oct - 27 Oct
Villa la Sugherella Tuscany sea, swimming pools spa family golf horse gym kneipp

20. 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 NZ$174
includes taxes & fees
28 Oct - 29 Oct
Botrona B&B
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

Find out more about Montemassi

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Montemassi holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Montemassi. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Montemassi. Seeing all the best attractions is bound to make you fall in love with Montemassi. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Montemassi short-term rentals, that won’t be hard to do.

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.