Calheta Vacation Rentals

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Check prices for these dates

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

Our top choices for Calheta vacation rentals

A swimming pool with a stone wall and a red door, surrounded by a mountainous landscape.

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
$230 nightly
The price is $230
Nov 12 - Nov 13
Total with taxes and fees
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
A swimming pool with a stone wall and a red door, surrounded by a mountainous landscape.

2. 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.
$228 nightly
The price is $228
Nov 12 - Nov 13
Total with taxes and fees
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
A coastal landscape with a stone wall, a grassy area, and a view of the ocean and mountains.

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.
$243 nightly
The price is $252
Nov 22 - Nov 23
Total with taxes and fees
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
A wooden table with a bottle of white wine, a glass, and bread slices. A stone building with a window is in the background.

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
$166 nightly
The price is $172
Nov 12 - Nov 13
Total with taxes and fees
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
A swimming pool with a stone wall and a red door, surrounded by a mountainous landscape.

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
$150 nightly
The price is $150
Nov 12 - Nov 13
Total with taxes and fees
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
A swimming pool with a stone wall and a red door, surrounded by a mountainous landscape.

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
$216 nightly
The price is $216
Nov 12 - Nov 13
Total with taxes and fees
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
$464 nightly
The price is $464
Nov 16 - Nov 17
Total with taxes and fees
Casa da Petra – Our Casa is your Casa
A stone building with a red roof, a paved pathway, and a view of the sea in the background.

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
$77 nightly
The price is $80
Nov 11 - Nov 12
Total with taxes and fees
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.
$343 nightly
The price is $343
Nov 12 - Nov 13
Total with taxes and fees
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
$166 nightly
The price is $166
Nov 14 - Nov 15
Total with taxes and fees
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
$302 nightly
The price is $302
Nov 12 - Nov 13
Total with taxes and fees
Apartment 'Ribeirinha 94' with Sea View and Wi-Fi
A living room with a black sofa, wooden coffee table, and a television.

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
$333 nightly
The price is $333
Nov 15 - Nov 16
Total with taxes and fees
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
A modern kitchen with a built-in stove, a dining area with white chairs, and a gray sofa.

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

Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
Ribeiras
$207 nightly
The price is $207
Nov 11 - Nov 12
Total with taxes and fees
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
A stone building with a red door, green shutters, and a balcony.

14. 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.
$377 nightly
The price is $377
Nov 12 - Nov 13
Total with taxes and fees
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.

15. 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
$281 nightly
The price is $281
Nov 12 - Nov 13
Total with taxes and fees
Vista da Baía - Casa do Aniceto Apartment with Sea View, Private Terrace & Wi-Fi
A cozy living room with a stone wall, a sofa, a round coffee table, and a TV.

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
$82 nightly
The price is $82
Nov 12 - Nov 13
Total with taxes and fees
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool and Wi-Fi
A stone-walled room with a white chair and table, a window, and a view of a landscape.

17. 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
$163 nightly
The price is $163
Nov 25 - Nov 26
Total with taxes and fees
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden 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
$551 nightly
The price is $551
Nov 15 - Nov 16
Total with taxes and fees
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.
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Find vacation rentals that suit your style

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Top Calheta Hotel Reviews

A patio with a table and chairs, a potted plant, and a view of the ocean and a mountain.
Casa d'Avó Guesthouse

Casa d'Avó Guesthouse

Casa d'Avó Guesthouse
Velas

10/10 Excellent

Perfect place to have a peaceful & enjoyable vacation😊
United States
Rina
Reviewed October 28, 2025
Casa d'Avó Guesthouse

Find out more about Calheta

Everything you need to know about Calheta vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Calheta vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Calheta vacation 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 low season months. For more hustle and bustle, you may prefer to visit Calheta in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $80 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Calheta rentals

At Expedia, we put the best Calheta vacation 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 vacation.

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 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.