A crowded beach with people swimming and sunbathing under umbrellas.

Holiday Rentals in Calheta

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Calheta holiday rentals

A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

1. Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
São Jorge
10.0 out of 10, Exceptional, (1 review)
"The view from the property was spectacular! Lucas was extremely helpful and kind. A unique experience that has made us wanting to come back again for a longer stay."
United States
Kimberly
The price is €281
includes taxes & fees
11 Sept - 12 Sept
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
A coastal landscape with a stone wall, a grassy area, and a view of the ocean and mountains.

2. Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
São Jorge
10.0 out of 10, Exceptional, (6 reviews)
"location, location, location plus the thoughtful design, adaptive reuse of structures, and the evident and abundant care of ownership and staff all added up to bliss for our group perhaps not for everyone, but the adventure of getting there and provisioning one’s stay can make for an even more satisfying stay."
United States
David B.
The price is €303
includes taxes & fees
4 Sept - 5 Sept
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

3. Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
São Jorge
10.0 out of 10, Exceptional, (2 reviews)
"serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso."
Portugal
Pedro E.
The price is €281
includes taxes & fees
8 Sept - 9 Sept
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

4. Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
Calheta
The price is €224
includes taxes & fees
26 Sept - 27 Sept
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

5. Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
São Jorge
The price is €204
includes taxes & fees
26 Sept - 27 Sept
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
A building with white doors and blue trim, a balcony with white railings, and a small window with a light fixture.

6. Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
Topo Calheta São Jorge Açores
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

7. Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba
São Jorge
The price is €263
includes taxes & fees
1 Sept - 2 Sept
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba
A dining table with two plates, two wine glasses, and a vase with a plant.

8. Casa da Petra – Our Casa is your Casa

Casa da Petra – Our Casa is your Casa
Urzelina
The price is €657
includes taxes & fees
28 Sept - 29 Sept
Casa da Petra – Our Casa is your Casa
A coastal town with a prominent white building with a red roof, surrounded by greenery and overlooking the sea.

9. Carpe Diem Apartment

Carpe Diem Apartment
Urzelina
The price is €141
includes taxes & fees
1 Sept - 2 Sept
Carpe Diem Apartment
A stone building with a red roof, a paved pathway, and a stone wall with a red railing.

10. Aldeia das Adegas

Aldeia das Adegas
4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (68 reviews)
"We had a great stay here."
United States
Nicholas
The price is €108
includes taxes & fees
22 Sept - 23 Sept
Aldeia das Adegas
A hotel room with a bed, a view through a door, and a balcony.

11. Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
Engrade
10.0 out of 10, Exceptional, (1 review)
"Pros: The house was recently renovated, everything was nice and clean, very kind host, peaceful place with view of the ocean and vineyards"
United States
Anonymous traveller
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
A garden pathway leading to a body of water with mountains in the background.

12. Casa do Jardim

Casa do Jardim
Santo Amaro
The price is €200
includes taxes & fees
18 Sept - 19 Sept
Casa do Jardim
A room with a wooden ceiling, a bed, a desk with a lamp, a fan, and a window.

13. Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is €149
includes taxes & fees
2 Sept - 3 Sept
Holiday Home 'Adega Pérola' with Wi-Fi
A stone wall with a wooden fence.

14. Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning

Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
Prainha
The price is €343
includes taxes & fees
4 Sept - 5 Sept
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
A stone-walled room with a white chair and table, a window, and a view of a landscape.

15. Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
Lajes do Pico
6.0 out of 10, (1 review)
"Pros: Die Ruhe, der Ausblick, der private Parkplatz, die schnelle Unterstützung durch die Ansprechperson, der Insektenschutz an Fenstern Cons: Schwierigkeit gehabt das Haus zu finden, da das einzige Schild am Haus selbst hängt und von der Straße aber nicht zu erkennen war; leichter Schimmel in der Dusche; penetranter Duft der Duftspender in Küche und Bad; Bettwäsche roch nicht sehr frisch"
Germany
Anonymous traveller
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
A stone building with a red door, green shutters, and a balcony.

16. Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
Pontas negras
7.0 out of 10, Good, (2 reviews)
"Nicley updated and clean but damp/musty smell. Location was good but required a drive to any attractions, restaurants, or markets. Balcony was nice but required access through the main bedroom. No communications on check-out procedures. Price was a bit high for what was offered."
United States
Eugene S.
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
A rectangular pool with clear blue water, surrounded by a tiled deck.

17. Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
Ribeiras
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
A modern living room with a wooden staircase, a sofa, a coffee table, and a dining area.

18. Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi

Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi
Pontas Negras
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & Wi-Fi
A spacious living area with a high wooden ceiling, a black leather sofa, and a dining area in the background.

19. Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace & Wi-Fi

Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace & Wi-Fi
Santo António SRP
The price is €263
includes taxes & fees
9 Sept - 10 Sept
Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace & Wi-Fi
A white building with grey trim, a stone wall, and a small garden with various plants.

20. Silveira House

Silveira House
Lajes do Pico
Silveira House
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 Calheta Hotel Reviews

Casa do Zé - AL

Casa do Zé - AL

10/10 Excellent
"Rosa was great and really welcoming! She also showed us the backyard with plants and coffee roasting process! The house is pretty, with washing machine and the kitchen well equipped. You can stay multiple days in casa do zè as the position is convenient to enjoy all the island."
Federica 4-night trip
Posted 2 weeks ago
Casa do Zé - AL

Find out more about Calheta

Everything you need to know about Calheta 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 Calheta 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 Calheta holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Calheta holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Calheta. 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 Calheta 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 Calheta holiday rentals we have selected for you start as low as €263 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Calheta rentals

At Expedia, we put the best Calheta 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 Calheta 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 Calheta 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 Calheta. 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 Calheta?

Yes, there are holiday rentals close to the most popular sights in Calheta, 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 Calheta has to offer?

Matilde's House, in the paradise Fajã de São João: This highly rated holiday home rental in Calheta is located by the ocean, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Calheta?

Choose from 13 Expedia holiday rentals in Calheta for a memorable holiday.

What can I see and do in Calheta?

Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge and Cascata do Cruzal are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Fajã dos Cubres and Pico da Esperanca.

What are holiday rentals like in Calheta?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Calheta. Holiday rentals feature extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family trip.