A crowded beach with people swimming and sunbathing under umbrellas.

Calheta Vacation Rentals

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Our top choices for Calheta vacation rentals

1. 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 CA $300
CA $353 total
includes taxes & fees
Sep 2 - Sep 3
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

2. 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 CA $283
CA $321 total
includes taxes & fees
Sep 4 - Sep 5
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

3. 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 CA $402
CA $468 total
includes taxes & fees
Sep 4 - Sep 5
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

4. 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 CA $386
CA $437 total
includes taxes & fees
Sep 11 - Sep 12
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

5. 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 CA $386
CA $434 total
includes taxes & fees
Sep 1 - Sep 2
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

6. 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 CA $370
CA $416 total
includes taxes & fees
Sep 1 - Sep 2
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

7. 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
The price is CA $265
CA $265 total
includes taxes & fees
Sep 1 - Sep 2
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

8. Carpe Noctem Apartment

Carpe Noctem Apartment
Urzelina
The price is CA $218
CA $227 total
includes taxes & fees
Sep 10 - Sep 11
Carpe Noctem Apartment

9. 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 CA $167
CA $174 total
includes taxes & fees
Sep 22 - Sep 23
Aldeia das Adegas

10. Carpe Diem Apartment

Carpe Diem Apartment
Urzelina
The price is CA $218
CA $227 total
includes taxes & fees
Sep 1 - Sep 2
Carpe Diem Apartment

11. Casa do Jardim

Casa do Jardim
Santo Amaro
The price is CA $305
CA $344 total
includes taxes & fees
Sep 18 - Sep 19
Casa do Jardim

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

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is CA $282
CA $380 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Home 'Adega Pérola' with Wi-Fi

13. Casa da Petra – Our Casa is your Casa

Casa da Petra – Our Casa is your Casa
Urzelina
The price is CA $702
CA $702 total
includes taxes & fees
Aug 29 - Aug 30
Casa da Petra – Our Casa is your Casa

14. Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
Lajes do Pico
The price is CA $127
CA $127 total
includes taxes & fees
Sep 4 - Sep 5
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

15. 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
The price is CA $451
CA $451 total
includes taxes & fees
Sep 6 - Sep 7
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

16. 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 CA $423
CA $551 total
includes taxes & fees
Sep 4 - Sep 5
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning

17. Silveira House

Silveira House
Lajes do Pico
The price is CA $72
CA $141 total
includes taxes & fees
Sep 6 - Sep 7
Silveira House

18. 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
The price is CA $392
CA $392 total
includes taxes & fees
Aug 29 - Aug 30
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

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

Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
Ribeiras
The price is CA $431
CA $431 total
includes taxes & fees
Sep 13 - Sep 14
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

20. 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 CA $335
CA $423 total
includes taxes & fees
Sep 4 - Sep 5
Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace & 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 Calheta Hotel Reviews

Find out more about Calheta

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Calheta. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Calheta?

Yes, there are vacation rentals near popular sights in Calheta, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Calheta?

Matilde's House, in the paradise Fajã de São João: Visitors give good reviews to this Calheta vacation home rental, which is located by the ocean and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Calheta?

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

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 larger area, you’ll find Fajã dos Cubres and Pico da Esperanca.

What are vacation rentals like in Calheta?

Vacation rentals are privately owned properties you can reserve for several days or more in Calheta. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.