A crowded beach with people swimming and sunbathing under umbrellas.

Calheta Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Calheta vacation 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 SAR 807
SAR 877 total
includes taxes & fees
16 Nov - 17 Nov
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.

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 SAR 861
SAR 961 total
includes taxes & fees
20 Nov - 21 Nov
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 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 SAR 587
SAR 656 total
includes taxes & fees
16 Nov - 17 Nov
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.

4. 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 SAR 530
SAR 575 total
includes taxes & fees
16 Nov - 17 Nov
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.

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 SAR 807
SAR 869 total
includes taxes & fees
16 Nov - 17 Nov
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.

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 SAR 765
SAR 827 total
includes taxes & fees
16 Nov - 17 Nov
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 SAR 1,721
SAR 1,721 total
includes taxes & fees
16 Nov - 17 Nov
Casa da Petra – Our Casa is your Casa
A row of stone buildings with red roofs, a central pathway, and a view of the sea.

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 SAR 286
SAR 298 total
includes taxes & fees
16 Nov - 17 Nov
Aldeia das Adegas
A covered outdoor seating area with a table and chairs, overlooking a scenic view of the sea and green landscape.

9. 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 SAR 522
SAR 1,275 total
includes taxes & fees
16 Nov - 17 Nov
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.

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

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
The price is SAR 341
SAR 618 total
includes taxes & fees
20 Nov - 21 Nov
Holiday Home 'Adega Pérola' with Wi-Fi
A compact kitchen with wooden cabinets, a built-in oven, and a dining area with a table and chairs.

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

Apartment 'Ribeirinha 94' with Sea View and Wi-Fi
Ribeirinha
The price is SAR 1,120
SAR 1,120 total
includes taxes & fees
18 Nov - 19 Nov
Apartment 'Ribeirinha 94' with Sea View and Wi-Fi
A stone wall with a wooden fence.

12. 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 SAR 908
SAR 1,236 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
A room with a wooden shelf unit, a sliding glass door leading to a balcony, and a view of buildings and a clear sky.

13. 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 SAR 1,222
SAR 1,399 total
includes taxes & fees
16 Nov - 17 Nov
Vacation Home "Casas Dos Vinagreiros - Pedro" 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.

14. Vista da Baía - Casa do Aniceto Apartment with Sea View, Private Terrace & Wi-Fi

Vista da Baía - Casa do Aniceto Apartment with Sea View, Private Terrace & Wi-Fi
Santo António SRP
The price is SAR 817
SAR 1,044 total
includes taxes & fees
16 Nov - 17 Nov
Vista da Baía - Casa do Aniceto Apartment with Sea View, Private Terrace & Wi-Fi
A rectangular pool with clear blue water, surrounded by a tiled deck.

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

Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
Ribeiras
The price is SAR 706
SAR 706 total
includes taxes & fees
1 Dec - 2 Dec
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
A poolside dining area with a view of the ocean, featuring burgers and fries on the table.

16. 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
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
A modern kitchen with a built-in stove, wooden dining table, and chairs. There is a wooden staircase with metal railings leading to an upper level.

17. 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 SAR 1,869
SAR 2,046 total
includes taxes & fees
16 Nov - 17 Nov
Vacation Home "Dos Vinagreiros - Guilherme" 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Calheta Hotel Reviews

Pico Dreams - Sportfish

Pico Dreams - Sportfish

10/10 Excellent
"Great location! Great staff. Safe and quiet"
Kathleen 2-night trip
Posted 1 month ago
Pico Dreams - Sportfish

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.