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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
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.
Pike Cliffs - Amazing view to S. Jorge
Casa Céu D'Abraão - You can click to enlarge the photo

Casa Céu D'Abraão - You can click to enlarge the photo

Lajes do Pico
With a stay at this vacation home in Lajes do Pico, you'll be on the waterfront, and 13.8 mi (22.2 km) from Whaler’s Museum and 14 mi (22.6 km) from Caiado ...
Casa Céu D'Abraão - You can click to enlarge the photo
Casa das Pereiras - Rural Tourism T1

Casa das Pereiras - Rural Tourism T1

Lajes do Pico, Açores
With a stay at this vacation home in Lajes do Pico, you'll be 11.7 mi (18.8 km) from Whaler’s Museum and 13 mi (20.9 km) from Caiado Lagoon.
Casa das Pereiras - Rural Tourism T1
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Casa da Esquila 2

Casa da Esquila 2

São Roque do Pico
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 ...
Casa da Esquila 2
Cantinho do Avô - Pico Island - Prainha, São Roque do Pico

Cantinho do Avô - Pico Island - Prainha, São Roque do Pico

Prainha de Baixo, São Roque do Pico
With a stay at this vacation home in Sao Roque do Pico, you'll be within a 15-minute drive of Sao Roque Church and Convent of Sao Roque do Pico.
Cantinho do Avô - Pico Island - Prainha, São Roque do Pico
Faidoca's Grandfather House - Four-Bedroom House

Faidoca's Grandfather House - Four-Bedroom House

Calheta de Nesquim
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 ...
Faidoca's Grandfather House - Four-Bedroom House
House Santana Pico Island Garden

House Santana Pico Island Garden

São Roque do Pico Açores
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.
House Santana Pico Island Garden
 AtlanticWindow - Modern House, Stunning View

AtlanticWindow - Modern House, Stunning View

São Roque do Pico
With a stay at this vacation home in Sao Roque do Pico, you'll be by the ocean, and 11.4 mi (18.3 km) from Sao Roque Church and 12.5 mi (20.1 km) from Convent ...
AtlanticWindow - Modern House, Stunning View
Blue House (Blue House)

Blue House (Blue House)

Urzelina
Located in Velas, this vacation home is by the ocean, within a 15-minute drive of Santa Bárbara Church and Igreja de Sao Jorge.
Blue House (Blue House)
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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
150 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Pike Cliffs - Amazing view to S. Jorge, Casa Céu D'Abraão - You can click to enlarge the photo, Casa das Pereiras - Rural Tourism T1, Casa da Esquila 2, Cantinho do Avô - Pico Island - Prainha, São Roque do Pico, Faidoca's Grandfather House - Four-Bedroom House, House Santana Pico Island Garden, AtlanticWindow - Modern House, Stunning View, Blue House (Blue House)

Top trending hotels in Calheta

Azores Youth Hostels - São Jorge

Azores Youth Hostels - São Jorge

2 out of 5
Canada da Vinha Nova, Fajã Grande, Calheta
When you stay at Azores Youth Hostels - São Jorge in Calheta, you'll be 15 minutes by car from Santa Bárbara Church.
Azores Youth Hostels - São Jorge
Kuanza Nature Experience

Kuanza Nature Experience

4 out of 5
Faja do Belo, Calheta, Azores
When you stay at Kuanza Nature Experience in Calheta, you'll be in a national park, you'll be a 5-minute drive from Fajãs das Lagoas de Santo Cristo e dos Cubres ...
Kuanza 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
With a stay at this vacation home in Calheta, you'll be on the waterfront, and 10.2 mi (16.4 km) from Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge ...
Matilde's House, in the paradise Fajã de São João
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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
With a stay at this apartment in Calheta, you'll be near the beach, and 22.3 mi (35.9 km) from Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge and ...
Apartment '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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