Book Holiday Homes in Calheta

Start date: Check-in selected.
To Date
End date: Check-out

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
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 ...
Opens in a new window AtlanticWindow - Modern House, Stunning View
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
Cagarra Nest Winery

Cagarra Nest Winery

Lajes do Pico Açores Azores
With a stay at this vacation home in Lajes do Pico, you'll be on the beach, and 12.3 mi (19.8 km) from Whaler’s Museum and 13.6 mi (21.9 km) from Caiado ...
Opens in a new windowCagarra Nest Winery
Save an average of 15% on thousands of hotels when you're signed in
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
Casa das Pereiras - Rural Tourism T2

Casa das Pereiras - Rural Tourism T2

Lajes do Pico, Açores Azores
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.
Opens in a new windowCasa das Pereiras - Rural Tourism T2
Panoramic Ocean Views from your Private Varand

Panoramic Ocean Views from your Private Varand

São Roque do Pico Açores
The price is AU$278 per night from 26 Dec to 27 Dec
AU$278
26 Dec - 27 Dec
includes taxes & fees
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
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
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 Açores
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 ...
Opens in a new windowCasa Céu D'Abraão - You can click to enlarge the photo
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
150 Holiday Homes
Lowest Price
AU$149
Highest Price
AU$377
Popular accommodation
AtlanticWindow - Modern House, Stunning View, Faidoca's Grandfather House - Four-Bedroom House, Cagarra Nest Winery, Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar, Casa da Esquila 2, Casa das Pereiras - Rural Tourism T2, Panoramic Ocean Views from your Private Varand, Pike Cliffs - Amazing view to S. Jorge, Casa Céu D'Abraão - You can click to enlarge the photo

Top trending hotels in Calheta

Kuanza Nature Experience

Kuanza Nature Experience

4 out of 5
Faja do Belo Calheta Azores
The price is AU$149 per night from 2 Jan to 3 Jan
AU$149
2 Jan - 3 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowKuanza Nature Experience
Azores Youth Hostels - São Jorge

Azores Youth Hostels - São Jorge

2 out of 5
Canada da Vinha Nova Calheta
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
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$377 per night from 2 Jan to 3 Jan
AU$377
2 Jan - 3 Jan 2026
includes taxes & fees
When you stay at this vacation home in Calheta, you'll be on the waterfront and within a 5-minute drive of Fajãs das Lagoas de Santo Cristo e dos Cubres de São ...
Opens in a new windowStylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
Save an average of 15% on thousands of hotels when you're signed in
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
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.