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

Pike Cliffs - Amazing view to S. Jorge

Pike Cliffs - Amazing view to S. Jorge

Prainha de Cima Azores
Stay at this business-friendly holiday home in Sao Roque do Pico. Enjoy daily housekeeping, a garden and laundry facilities. Popular attractions Caiado Lagoon ...
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
Stay at this beach holiday home in Lajes do Pico. Enjoy free Wi-Fi, a beach locale and a garden.
Opens in a new windowFaidoca's Grandfather House - Four-Bedroom House
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
Stay at this holiday home in Lajes do Pico. Enjoy free Wi-Fi, a garden and laundry facilities.
Opens in a new windowCasa Céu D'Abraão - You can click to enlarge the photo
Save an average of 15% on thousands of hotels when you're signed in
House Santana Pico Island Garden

House Santana Pico Island Garden

São Roque do Pico Açores Azores
Stay at this holiday home in Sao Roque do Pico. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions A Buraca Winery and Convent of Sao Roque ...
Opens in a new windowHouse Santana Pico Island Garden
New Family Home with a View of São Jorge Island – Ribeirinha

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

Ribeirinha
Stay at this holiday home in Lajes do Pico. Enjoy laundry facilities, balconies and cable/satellite TV service.
Opens in a new windowNew Family Home with a View of São Jorge Island – Ribeirinha
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
Stay at this holiday home in Sao Roque do Pico. Enjoy air conditioning. Popular attractions Convent of Sao Roque do Pico and A Buraca Winery are located ...
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
Stay at this holiday home in Sao Roque do Pico. Enjoy laundry facilities and an in-room coffee maker. Popular attractions Convent of Sao Roque do Pico and A ...
Opens in a new windowCasa 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 Azores
Stay at this holiday home in Sao Roque do Pico. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Convent of Sao Roque do Pico and A Buraca ...
Opens in a new windowPICO Hollidays Rentals- Mountain and sea view for families or groups
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
Stay at this holiday home in Sao Roque do Pico. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Caiado Lagoon and Whaler’s Museum are ...
Opens in a new windowEnchanting view from the balcony of beautifully restored "Adega Baia do Canto".
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
129 Holiday Homes
Lowest Price
NZ$91
Highest Price
NZ$538
Popular accommodation
Pike Cliffs - Amazing view to S. Jorge, Faidoca's Grandfather House - Four-Bedroom House, Casa Céu D'Abraão - You can click to enlarge the photo, House Santana Pico Island Garden, New Family Home with a View of São Jorge Island – Ribeirinha, Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar, Casa da Esquila 2, PICO Hollidays Rentals- Mountain and sea view for families or groups, Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".

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 NZ$91 per night from 10 May to 11 May
NZ$91
10 May - 11 May
includes taxes & fees
Stay at this hostel in Calheta. Enjoy free breakfast, free parking and a garden. Popular attractions Fajã dos Cubres and Fajãs das Lagoas de Santo Cristo e dos ...
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 NZ$405 per night from 7 May to 8 May
NZ$405
7 May - 8 May
includes taxes & fees
Stay at this family-friendly hotel in Calheta. Enjoy free Wi-Fi, 2 outdoor pools and in-room massages. Popular attractions Fajãs das Lagoas de Santo Cristo e ...
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
Stay at this holiday home in Calheta. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attraction Cascata do Cruzal is located ...
Opens in a new windowMatilde's House, in the paradise Fajã de São João
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$538 per night from 7 May to 8 May
NZ$538
7 May - 8 May
includes taxes & fees
Stay at this holiday home in Calheta. Enjoy a garden, patios and an in-room coffee maker. Popular attractions Fajãs das Lagoas de Santo Cristo e dos Cubres de ...
Opens in a new windowStylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
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.