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Featured Holiday Homes in Calheta

Faidoca's Grandfather House - Four-Bedroom House

Faidoca's Grandfather House - Four-Bedroom House

Calheta de Nesquim Azores
With a stay at this vacation home, you'll be centrally located in Lajes do Pico, 11.6 mi (18.7 km) from Whaler’s Museum and 12.9 mi (20.7 km) from Caiado ...
Opens in a new windowFaidoca's Grandfather House - Four-Bedroom House
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
When you stay at this vacation home in Lajes do Pico, you'll be 10 minutes by car from Whaler’s Museum.
Opens in a new windowVacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
Pico Azores - Family house S. Jorge view

Pico Azores - Family house S. Jorge view

Ribeirinha
With a stay at this vacation home in Lajes do Pico, you'll be 11.9 mi (19.2 km) from Caiado Lagoon and 13.8 mi (22.1 km) from Sao Roque Church.
Opens in a new windowPico Azores - Family house S. Jorge view
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Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar

Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar

São Roque do Pico Açores
With a stay at this vacation home in Sao Roque do Pico, you'll be by the ocean, just steps from Sao Roque Church and a 2-minute drive from Convent of Sao Roque ...
Opens in a new windowPico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Engrade
The price is AU$433 per night from 16 May to 17 May
AU$433
16 May - 17 May
includes taxes & fees
With a stay at this vacation home in Lajes do Pico, you'll be 14.4 mi (23.2 km) from Whaler’s Museum and 14.7 mi (23.7 km) from Caiado Lagoon.
Opens in a new windowVacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
Casa da Esquila 2

Casa da Esquila 2

São Roque do Pico Açores
When you stay at this vacation home in Sao Roque do Pico, you'll be by the sea, within a 5-minute drive of Convent of Sao Roque do Pico and Sao Roque ...
Opens in a new windowCasa da Esquila 2
Pike Cliffs - Amazing view to S. Jorge

Pike Cliffs - Amazing view to S. Jorge

Prainha de Cima Azores
Located in Sao Roque do Pico, this vacation home is by the sea, within a 15-minute drive of Sao Roque Church and Convent of Sao Roque do Pico.
Opens in a new windowPike Cliffs - Amazing view to S. Jorge
Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".

Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".

Santo Amaro, Sao Roque, Ilha do Pico, Azores Unknown
With a stay at this vacation home in Sao Roque do Pico, you'll be 9.8 mi (15.7 km) from Sao Roque Church and 10.9 mi (17.5 km) from Convent of Sao Roque do ...
Opens in a new windowEnchanting view from the balcony of beautifully restored "Adega Baia do Canto".
PICO Hollidays  Rentals- Mountain and sea view for families or  groups

PICO Hollidays Rentals- Mountain and sea view for families or groups

São Roque do Pico Azores
When you stay at this vacation home in Sao Roque do Pico, you'll be on the waterfront, within a 5-minute drive of Convent of Sao Roque do Pico and Sao Roque ...
Opens in a new windowPICO Hollidays Rentals- Mountain and sea view for families or groups
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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.

Calheta Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Calheta vacation homes are the perfect way for you to wing it.

Holiday houses in Calheta let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Calheta in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Calheta adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Calheta with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Calheta vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Calheta Holiday Homes essential information

Accommodation
125 Holiday Homes
Lowest Price
AU$74
Highest Price
AU$442
Popular accommodation
Faidoca's Grandfather House - Four-Bedroom House, Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi, Pico Azores - Family house S. Jorge view, Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar, Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi, Casa da Esquila 2, Pike Cliffs - Amazing view to S. Jorge, Enchanting view from the balcony of beautifully restored "Adega Baia do Canto"., PICO Hollidays Rentals- Mountain and sea view for families or groups

Top trending hotels in Calheta

Azores Youth Hostels - São Jorge

Azores Youth Hostels - São Jorge

2 out of 5
Canada da Vinha Nova Calheta
The price is AU$74 per night from 16 May to 17 May
AU$74
16 May - 17 May
includes taxes & fees
When you stay at Azores Youth Hostels - São Jorge in Calheta, you'll be 15 minutes by car from Santa Bárbara Church.
Opens in a new windowAzores Youth Hostels - São Jorge
Kuanza Nature Experience

Kuanza Nature Experience

4 out of 5
Faja do Belo Calheta Azores
The price is AU$329 per night from 19 May to 20 May
AU$329
19 May - 20 May
includes taxes & fees
With a stay at Kuanza Nature Experience in Calheta, you'll be in a national park and within the region of Fajãs das Lagoas de Santo Cristo e dos Cubres de São ...
Opens in a new windowKuanza Nature Experience
Matilde's House, in the paradise Fajã de São João

Matilde's House, in the paradise Fajã de São João

Santo Antão, São Jorge Azores
When you stay at this vacation home in Calheta, you'll be on the waterfront and 11 minutes by car from Cascata do Cruzal.
Opens in a new windowMatilde's House, in the paradise Fajã de São João
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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 Azores
The price is AU$442 per night from 17 May to 18 May
AU$442
17 May - 18 May
includes taxes & fees
When you stay at this vacation home in Calheta, you'll be on the waterfront and within a short 1-minute drive from Fajãs das Lagoas de Santo Cristo e dos Cubres ...
Opens in a new windowStylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
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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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^Subject to availability and chosen travel dates.