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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Calheta vacation rentals

A circular infinity pool with two levels, surrounded by stone steps, overlooking a clear blue sea.

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
$164 nightly
The price is $164
Nov 2 - Nov 3
Total with taxes and fees
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.

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
$180 nightly
The price is $187
Nov 2 - Nov 3
Total with taxes and fees
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
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.
$263 nightly
The price is $273
Nov 2 - Nov 3
Total with taxes and fees
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.

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
$250 nightly
The price is $250
Nov 2 - Nov 3
Total with taxes and fees
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.

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.
$249 nightly
The price is $249
Nov 2 - Nov 3
Total with taxes and fees
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
$236 nightly
The price is $236
Nov 2 - Nov 3
Total with taxes and fees
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba
A stone building with a red roof, a paved pathway, and a stone wall with a red railing.

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
$78 nightly
The price is $81
Nov 1 - Nov 2
Total with taxes and fees
Aldeia das Adegas
A stone building with a tiled roof, a staircase leading to a seating area with chairs, and lush greenery surrounding the property.

8. Casa do Laureano

Casa do Laureano
Santo Amaro
$138 nightly
The price is $138
Oct 17 - Oct 18
Total with taxes and fees
Casa do Laureano
A room with a wooden ceiling, a bed, a desk with a lamp, a fan, and a window.

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

Holiday Home 'Adega Pérola' with Wi-Fi
Cais do Galego
$167 nightly
The price is $167
Oct 16 - Oct 17
Total with taxes and fees
Holiday Home 'Adega Pérola' with Wi-Fi
A dining table with two plates, two wine glasses, and a vase with a plant.

10. Casa da Petra – Our Casa is your Casa

Casa da Petra – Our Casa is your Casa
Urzelina
$466 nightly
The price is $466
Oct 19 - Oct 20
Total with taxes and fees
Casa da Petra – Our Casa is your Casa
A stone building with a wooden deck, a table, and chairs.

11. 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
$205 nightly
The price is $205
Oct 17 - Oct 18
Total with taxes and fees
Casa da Terra Alta
A covered outdoor seating area with a table and chairs, overlooking a scenic view of the sea and green landscape.

12. 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.
$345 nightly
The price is $345
Nov 1 - Nov 2
Total with taxes and fees
Pico Azores - Family house S. Jorge view
A poolside dining area with a view of the ocean, featuring burgers and fries on the table.

13. 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 1 - Nov 2
Total with taxes and fees
Holiday Home 'Pico Boutique House' with Mountain View, Shared Pool 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
$246 nightly
The price is $246
Nov 1 - Nov 2
Total with taxes and fees
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
A white building with grey trim, a stone wall, and a small garden with various plants.

15. Silveira House

Silveira House
Lajes do Pico
$99 nightly
The price is $99
Oct 26 - Oct 27
Total with taxes and fees
Silveira House
A stone-walled room with a white chair and table, a window, and a view of a landscape.

16. 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
$123 nightly
The price is $123
Oct 31 - Nov 1
Total with taxes and fees
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
A compact kitchen with wooden beams, a built-in oven, a microwave, and a refrigerator.

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

Apartment 'Ribeirinha 94' with Sea View and Wi-Fi
Ribeirinha
$303 nightly
The price is $303
Oct 18 - Oct 19
Total with taxes and fees
Apartment 'Ribeirinha 94' with Sea View and Wi-Fi
A stone wall with a wooden fence.

18. 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
$384 nightly
The price is $384
Oct 12 - Oct 13
Total with taxes and fees
Holiday Home 'Ocean Melody' with Sea View, Wi-Fi and Air Conditioning
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
$197 nightly
The price is $197
Oct 13 - Oct 14
Total with taxes and fees
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
A spacious living area with a high wooden ceiling, a black leather sofa, and a dining area in the background.

20. 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
$283 nightly
The price is $283
Oct 18 - Oct 19
Total with taxes and fees
Vista da Baía - Casa do Aniceto Apartment 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

Casa d'Avó Guesthouse

Casa d'Avó Guesthouse

10/10 Excellent
"The location is fantastic, right on the oceanfront and a perfect base for exploring the island. The property is spotless, well-maintained, and has a wonderful atmosphere. There’s a shared kitchen with large, dedicated storage cabinets for each room, and it's fully equipped with everything you could possibly need. The service was impeccable—Paula and Diana were always accessible, welcoming, and spoke excellent English. They went above and beyond to provide everything we needed with genuine generosity. Highly recommended!"
Miron 5-night trip
Posted 6 days ago
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 $81 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.