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 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 $205
CA $234 total
includes taxes & fees
Nov 2 - Nov 3
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

2. 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 $227
CA $265 total
includes taxes & fees
Nov 2 - Nov 3
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

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 $333
CA $392 total
includes taxes & fees
Nov 2 - Nov 3
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

4. 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 $296
CA $338 total
includes taxes & fees
Nov 2 - Nov 3
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

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 $312
CA $355 total
includes taxes & fees
Nov 2 - Nov 3
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

6. 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 $312
CA $355 total
includes taxes & fees
Nov 2 - Nov 3
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

7. Aldeia das Adegas

Aldeia das Adegas
4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (70 reviews)
"We had a great stay here."
United States
Nicholas
The price is CA $111
CA $115 total
includes taxes & fees
Nov 1 - Nov 2
Aldeia das Adegas

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

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is CA $140
CA $248 total
includes taxes & fees
Oct 12 - Oct 13
Holiday Home 'Adega Pérola' with Wi-Fi

9. Casa do Laureano

Casa do Laureano
Santo Amaro
The price is CA $168
CA $197 total
includes taxes & fees
Oct 25 - Oct 26
Casa do Laureano

10. Casa da Terra Alta

Casa da Terra Alta
Santo Amaro
The price is CA $264
CA $298 total
includes taxes & fees
Oct 17 - Oct 18
Casa da Terra Alta

11. Pico Azores - Family house S. Jorge view

Pico Azores - Family house S. Jorge view
Ribeirinha
10.0 out of 10, Exceptional, (1 review)
"Nous étions 2 familles et avons passé une superbe semaine. Les chambres sont bien divisées et il y avait le nécessaire pour notre séjour. La maison est très propre et très belle."
United States
Amélie T.
The price is CA $202
CA $493 total
includes taxes & fees
Nov 1 - Nov 2
Pico Azores - Family house S. Jorge view

12. Casa da Petra – Our Casa is your Casa

Casa da Petra – Our Casa is your Casa
Urzelina
The price is CA $666
CA $666 total
includes taxes & fees
Oct 20 - Oct 21
Casa da Petra – Our Casa is your Casa

13. Silveira House

Silveira House
Lajes do Pico
The price is CA $72
CA $141 total
includes taxes & fees
Oct 9 - Oct 10
Silveira House

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 $117
CA $117 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi

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
The price is CA $176
CA $176 total
includes taxes & fees
Oct 9 - Oct 10
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

16. 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 $351
CA $351 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

17. Cantinho das Japoneiras

Cantinho das Japoneiras
Velas, São Jorge, Açores
4.0 out of 10, (1 review)
"L'host non rispondeva alle e mail per ricevere le istruzioni per il check in. Dopo aver fatto presente la difficoltà in netto anticipo sia ad Expedia che a Vrbo (canale di Expedia) non si sono allertati per trovare qualcosa di alternativo. L'host ci ha contattato dopo un bel po' dal nostro arrivo, perché intanto abbiamo comunque preso il volo. l'indirizzo su booking non era preciso e ovviamente l'host non rispondeva alla richiesta di invio .Alla fine l'host si è presentato all'appartamento ed...
Italy
Rosaria Anna
The price is CA $308
CA $384 total
includes taxes & fees
Oct 10 - Oct 11
Cantinho das Japoneiras

18. 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 $281
CA $281 total
includes taxes & fees
Oct 13 - Oct 14
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi

19. 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 $421
CA $548 total
includes taxes & fees
Oct 8 - Oct 9
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning

20. Apartment 'Ribeirinha 94' with Sea View and Wi-Fi

Apartment 'Ribeirinha 94' with Sea View and Wi-Fi
Ribeirinha
The price is CA $433
CA $433 total
includes taxes & fees
Oct 18 - Oct 19
Apartment 'Ribeirinha 94' with Sea View and 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.