A crowded beach with people swimming and sunbathing under umbrellas.

Calheta 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 Calheta vacation rentals

A coastal landscape with a stone wall, a grassy area, and a view of the ocean and mountains.

1. 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 ￥36,738
￥42,976 total
includes taxes & fees
Nov 2 - Nov 3
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.

2. 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 ￥34,442
￥39,388 total
includes taxes & fees
Nov 2 - Nov 3
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
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 ￥34,442
￥38,858 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥25,081
￥29,617 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥22,608
￥25,787 total
includes taxes & fees
Nov 2 - Nov 3
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

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 ￥32,676
￥36,915 total
includes taxes & fees
Nov 2 - Nov 3
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.

7. Casa da Petra – Our Casa is your Casa

Casa da Petra – Our Casa is your Casa
Urzelina
The price is ￥73,494
￥73,494 total
includes taxes & fees
Oct 19 - Oct 20
Casa da Petra – Our Casa is your Casa
A stone building with a red roof, a paved pathway, and a stone wall with a red railing.

8. 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 ￥12,228
￥12,717 total
includes taxes & fees
Nov 15 - Nov 16
Aldeia das Adegas
A stone building with a wooden deck, a table, and chairs.

9. Casa da Terra Alta

Casa da Terra Alta
Santo Amaro
10.0 out of 10, Exceptional, (1 review)
"We had great stay, a fabulous place to sit and enjoy the view in the evening. The house was comfortable and had everything we needed. Bed linens and towels were of good quality, not always the case in some places we have stayed in. Erica was a lovely host; you could tell she cared very much for the house and garden. We would recommend Highland Homes to anyone going to Pico Island!"
Canada
Anonymous traveler
The price is ￥26,494
￥30,203 total
includes taxes & fees
Oct 17 - Oct 18
Casa da Terra Alta
A covered outdoor seating area with a table and chairs, overlooking a scenic view of the sea and green landscape.

10. 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 ￥22,294
￥54,440 total
includes taxes & fees
Nov 1 - Nov 2
Pico Azores - Family house S. Jorge view
A room with a wooden ceiling, a bed, a desk with a lamp, a fan, and a window.

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

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is ￥15,510
￥27,358 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Home 'Adega Pérola' with Wi-Fi
A stone building with a tiled roof, a staircase leading to a seating area with chairs, and lush greenery surrounding the property.

12. Casa do Laureano

Casa do Laureano
Santo Amaro
The price is ￥18,546
￥21,725 total
includes taxes & fees
Oct 17 - Oct 18
Casa do Laureano
A bedroom with a stone wall, a wooden ceiling, a bed with white bedding, a red door, and a wooden cabinet.

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

Apartment 'Ribeirinha 94' with Sea View and Wi-Fi
Ribeirinha
The price is ￥47,821
￥47,821 total
includes taxes & fees
Oct 18 - Oct 19
Apartment 'Ribeirinha 94' with Sea View and Wi-Fi
A hotel room with a bed, a view through a door, and a balcony.

14. 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 traveler
The price is ￥38,773
￥38,773 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
A modern living room with a wooden staircase, a sofa, a coffee table, and a dining area.

15. 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
The price is ￥79,805
￥87,345 total
includes taxes & fees
Oct 16 - Oct 17
Vacation Home "Dos Vinagreiros - Guilherme" with Sea View, Private Terrace & 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.
The price is ￥52,181
￥59,721 total
includes taxes & fees
Oct 16 - Oct 17
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
A white building with grey trim, a stone wall, and a small garden with various plants.

17. Silveira House

Silveira House
Lajes do Pico
The price is ￥7,948
￥15,543 total
includes taxes & fees
Oct 26 - Oct 27
Silveira House
A poolside dining area with a view of the ocean, featuring burgers and fries on the table.

18. 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 ￥12,925
￥12,925 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
A rectangular pool with clear blue water, surrounded by a tiled deck.

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 ￥31,019
￥31,019 total
includes taxes & fees
Oct 20 - Oct 21
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
A stone-walled room with a white chair and table, a window, and a view of a landscape.

20. 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 traveler
The price is ￥19,386
￥19,386 total
includes taxes & fees
Oct 31 - Nov 1
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden 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

Casa do Zé - AL

Casa do Zé - AL

10/10 Excellent
"C’est la dernière maison au bout du chemin. La terrasse sur la photo est en haut à gauche sur le chemin de pierre , non annexée à la maison. La vue est incroyable."
Nathalie Ann 6-night trip
Posted 1 month ago
Casa do Zé - AL

Find out more about Calheta

Search for holiday rentals in Calheta on Expedia! You can easily find your home rentals, villas, holiday apartments in Calheta using one of the methods below:

  • View our selection of featured holiday rentals in Calheta
  • Use the map to find apartments and other holiday homes in the Calheta neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Calheta while they last

Look no further and take a look at our great range of rental properties in Calheta!

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.