Book Holiday Homes in Calheta

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Featured Holiday Homes in Calheta

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
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
Panoramic Ocean Views from your Private Varand

Panoramic Ocean Views from your Private Varand

São Roque do Pico Açores
Located in Sao Roque do Pico, this vacation home is a 3-minute drive from A Buraca Winery and 6 minutes from Convent of Sao Roque do Pico.
Opens in a new windowPanoramic Ocean Views from your Private Varand
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New Family Home with a View of São Jorge Island – Ribeirinha

New Family Home with a View of São Jorge Island – Ribeirinha

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 windowNew Family Home with a View of São Jorge Island – Ribeirinha
House Santana Pico Island Garden

House Santana Pico Island Garden

São Roque do Pico Açores Azores
Located in Sao Roque do Pico, this vacation home is by the sea, a 3-minute drive from A Buraca Winery and 5 minutes from Convent of Sao Roque do Pico.
Opens in a new windowHouse Santana Pico Island Garden
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
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
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$67
Highest Price
AU$498
Popular accommodation
Pike Cliffs - Amazing view to S. Jorge, Faidoca's Grandfather House - Four-Bedroom House, Panoramic Ocean Views from your Private Varand, New Family Home with a View of São Jorge Island – Ribeirinha, House Santana Pico Island Garden, Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar, Casa da Esquila 2, 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$67 per night from 31 Mar to 1 Apr
AU$67
31 Mar - 1 Apr
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
Fajã da Caldeira House - AL

Fajã da Caldeira House - AL

Ribeira Seca - São Jorge - Açores Azores
When you stay at this cottage in Calheta, you'll be on the waterfront and 5 minutes by foot from Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge.
Opens in a new windowFajã da Caldeira House - AL
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 Azores
The price is AU$498 per night from 7 Apr to 8 Apr
AU$498
7 Apr - 8 Apr
includes taxes & fees
When you stay at this vacation home in Calheta, you'll be by the ocean and within a short 1-minute drive from Fajãs das Lagoas de Santo Cristo e dos Cubres de ...
Opens in a new windowStylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
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Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

Topo Calheta São Jorge Açores
Fully refundable
The price is AU$175 per night from 31 Mar to 1 Apr
AU$175
31 Mar - 1 Apr
includes taxes & fees
When you stay at this apartment in Calheta, you'll be 5 minutes by car from Cascata do Cruzal.
Opens in a new windowApartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
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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.