Book Holiday Homes in Calheta

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Calheta

 AtlanticWindow - Modern House, Stunning View

AtlanticWindow - Modern House, Stunning View

São Roque do Pico
Book a stay at this family-friendly vacation home in Sao Roque do Pico. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attraction Caiado Lagoon ...
AtlanticWindow - Modern House, Stunning View
Pike Cliffs - Amazing view to S. Jorge

Pike Cliffs - Amazing view to S. Jorge

Prainha de Cima
Book a stay at this business-friendly vacation home in Sao Roque do Pico. Enjoy a water park, daily housekeeping, and a garden. Popular attractions Caiado Lagoon ...
Pike 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, Az
Stay at this vacation home in Sao Roque do Pico. Enjoy free WiFi, a garden, and patios. Popular attractions Caiado Lagoon and Whaler’s Museum are located ...
Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".
Save an average of 15% on thousands of hotels when you're signed in
Charming 3-bedroom house with WiFi, AC in adorable Manadas

Charming 3-bedroom house with WiFi, AC in adorable Manadas

Manadas
Stay at this vacation home in Velas. Enjoy air conditioning. Popular attractions Santa Bárbara Church and Pico da Esperanca are located nearby.
Charming 3-bedroom house with WiFi, AC in adorable Manadas
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
Stay at this vacation home in Sao Roque do Pico. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Caiado Lagoon and Whaler’s Museum are ...
Cantinho do Avô - Pico Island - Prainha, São Roque do Pico
Beautiful 3 bedroom & 3 bathrooms House with Sea view in São Jorge, Açores

Beautiful 3 bedroom & 3 bathrooms House with Sea view in São Jorge, Açores

Açores
Stay at this vacation home in Calheta. Enjoy an in-room coffeemaker and housekeeping.
Beautiful 3 bedroom & 3 bathrooms House with Sea view in São Jorge, Açores
Casa da Esquila 2

Casa da Esquila 2

São Roque do Pico
Stay at this vacation home in Sao Roque do Pico. Enjoy an in-room coffeemaker. Popular attractions Convent of Sao Roque do Pico and Sao Roque Church are located ...
Casa da Esquila 2
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
Stay at this vacation home in Sao Roque do Pico. Enjoy free WiFi, a garden, and furnished balconies. Popular attractions Convent of Sao Roque do Pico and Sao ...
PICO Hollidays Rentals- Mountain and sea view for families or groups
Faidoca's Grandfather House - Four-Bedroom House

Faidoca's Grandfather House - Four-Bedroom House

Calheta de Nesquim
Book a stay at this beach vacation home in Lajes do Pico. Enjoy free WiFi, a beach locale, and a water park.
Faidoca's Grandfather House - Four-Bedroom House
Don't see what you're looking for?
See all available properties in Calheta
View all properties
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
147 Holiday Homes
Lowest Price
NZ$109
Highest Price
NZ$537
Popular accommodation
AtlanticWindow - Modern House, Stunning View, Pike Cliffs - Amazing view to S. Jorge, Enchanting view from the balcony of beautifully restored "Adega Baia do Canto"., Charming 3-bedroom house with WiFi, AC in adorable Manadas, Cantinho do Avô - Pico Island - Prainha, São Roque do Pico, Beautiful 3 bedroom & 3 bathrooms House with Sea view in São Jorge, Açores, Casa da Esquila 2, PICO Hollidays Rentals- Mountain and sea view for families or groups, Faidoca's Grandfather House - Four-Bedroom 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
The price is NZ$109 per night from 4 Apr to 5 Apr
NZ$109
includes taxes & fees
4 Apr - 5 Apr
Stay at this hostel in Calheta. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Santa Bárbara Church and Fajãs das Lagoas de ...
Azores Youth Hostels - São Jorge
Kuanza Nature Experience

Kuanza Nature Experience

4 out of 5
Faja do Belo, Calheta, Azores
The price is NZ$378 per night from 4 Apr to 5 Apr
NZ$378
includes taxes & fees
4 Apr - 5 Apr
Stay at this 4-star family-friendly hotel in Calheta. Enjoy free WiFi, 2 outdoor pools, and in-room massages. Popular attraction Fajãs das Lagoas de Santo Cristo ...
Kuanza Nature Experience
Beautiful 3 bedroom & 3 bathrooms House with Sea view in São Jorge, Açores

Beautiful 3 bedroom & 3 bathrooms House with Sea view in São Jorge, Açores

Açores
Stay at this vacation home in Calheta. Enjoy an in-room coffeemaker and housekeeping.
Beautiful 3 bedroom & 3 bathrooms House with Sea view in São Jorge, Açores
Save an average of 15% on thousands of hotels when you're signed in
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
The price is NZ$537 per night from 4 Apr to 5 Apr
NZ$537
includes taxes & fees
4 Apr - 5 Apr
Book a stay at this family-friendly vacation home in Calheta. Enjoy free WiFi, a garden, and patios. Popular attraction Fajãs das Lagoas de Santo Cristo e dos ...
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
Don't see what you're looking for?
See all available properties in Calheta
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.