Calheta Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Calheta holiday rentals

The price is AU$120
includes taxes & fees
19 Jan - 20 Jan
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
10.0 out of 10, Exceptional, (4 reviews)
"location, location, location plus the thoughtful design, adaptive reuse of structures, and the evident and abundant care of ownership and staff all added up to bliss for our group perhaps not for everyone, but the adventure of getting there and provisioning one’s stay can make for an even more satisfying stay."
United States
David B.
The price is AU$424
includes taxes & fees
18 Jan - 19 Jan
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
10.0 out of 10, Exceptional, (1 review)
"serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso."
Portugal
Pedro E.
The price is AU$385
includes taxes & fees
18 Jan - 19 Jan
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
The price is AU$256
includes taxes & fees
19 Jan - 20 Jan
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
The price is AU$290
includes taxes & fees
18 Jan - 19 Jan
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
The price is AU$364
includes taxes & fees
18 Jan - 19 Jan
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba
The price is AU$385
includes taxes & fees
18 Jan - 19 Jan
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

Apartment in Sao Roque do Pico

Aldeia das Adegas
4.0 star property
9.4 out of 10, Exceptional, (64 reviews)
"Diana is friendly and responsive with our requests. We stayed at one bedroom apartment. It feels like staying at home but in the paradise. "
United States
Raechung
The price is AU$174
includes taxes & fees
21 Jan - 22 Jan
Aldeia das Adegas

Holiday Home in São Roque do Pico

Vila Paim - Apart. Low
10.0 out of 10, Exceptional, (1 review)
"Great getaway super quiet and very relaxing place."
United States
Joe F.
The price is AU$268
includes taxes & fees
18 Jan - 19 Jan
Vila Paim - Apart. Low

Holiday Home in São Roque do Pico

Casa dos Felicias
10.0 out of 10, Exceptional, (1 review)
"The house was clean, spacious, well-appointed, convenient to the port, swimming, the grocery, the church, the village center, shops, and had gorgeous views. "
United States
Maria N.
The price is AU$268
includes taxes & fees
18 Jan - 19 Jan
Casa dos Felicias

Holiday Home in São Roque do Pico

Adega do Mirante
8.0 out of 10, Very good, (1 review)
"The basic necessities are provided; beds are comfortable and the place is clean. Need to Whatsapp owner to get information to get onto the property because messaging in Portugese otherwise. Property said air conditioning but the air conditioning was broken. It was cool enough though so not a problem. Walkable to the ocean and natural pool and nice restaurant down the street. It is located in Sao Roque which is in the middle of the island so nothing is far away if you are driving. Parking ample...
United States
Sharon
The price is AU$268
includes taxes & fees
20 Jan - 21 Jan
Adega do Mirante

Holiday Home in Lajes do Pico

Silveira House
The price is AU$156
includes taxes & fees
18 Jan - 19 Jan
Silveira House
The price is AU$297
includes taxes & fees
28 Jan - 29 Jan
Very well equipped apartment in the center of São Roque do Pico
"I stayed in this apartment with my family of 4. The apartment itself was small but ok. Note that the management keeps the remote control for AC and if you need it, they charge a daily fee of 10EUR per day. The communication with the manager has been very difficult since the beginning. I’ve sent a message a month prior to arrival to confirm there was enough room for the 4 of us. I never got any answers. The day before our arrival, I sent another message that was again unanswered. Even VRBO...
Canada
Caroline P.
The price is AU$315
includes taxes & fees
20 Jan - 21 Jan
Very well equipped apartment in the center of São Roque do Pico

Holiday Home in Cais do Galego

Holiday Home 'Adega Pérola' with Wi-Fi
The price is AU$258
includes taxes & fees
21 Jan - 22 Jan
Holiday Home 'Adega Pérola' with Wi-Fi
10.0 out of 10, Exceptional, (1 review)
"Pros: The house was recently renovated, everything was nice and clean, very kind host, peaceful place with view of the ocean and vineyards"
United States
Anonymous traveller
The price is AU$380
includes taxes & fees
17 Feb - 18 Feb
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Holiday Home in São Roque do Pico

Vila Paim - Apart. DELUX
The price is AU$416
includes taxes & fees
18 Jan - 19 Jan
Vila Paim - Apart. DELUX

Holiday Home in São Roque do Pico

Panoramic Ocean Views from your Private Varand
The price is AU$274
includes taxes & fees
20 Jan - 21 Jan
Panoramic Ocean Views from your Private Varand
2.0 star property
The price is AU$304
includes taxes & fees
18 Jan - 19 Jan
Apartment 'Branca' with Sea View, Private Terrace and Wi-Fi
The price is AU$613
includes taxes & fees
17 Feb - 18 Feb
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Calheta Hotel Reviews

Find out more about Calheta

Everything you need to know about Calheta holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Calheta holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Calheta holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Calheta holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Calheta. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Calheta holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Calheta holiday rentals we have selected for you start as low as AU$120 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Calheta rentals

At Expedia, we put the best Calheta holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Calheta rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Calheta holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Calheta. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Calheta?

Yes, there are holiday rentals close to the most popular sights in Calheta, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Calheta has to offer?

Matilde's House, in the paradise Fajã de São João: This highly rated holiday home rental in Calheta is located by the ocean, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Another good choice for your trip to Calheta is Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf).

How many holiday rentals will I find in Calheta?

Choose from 12 Expedia holiday rentals in Calheta for a memorable holiday.

What can I see and do in Calheta?

Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge and Cascata do Cruzal are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Fajã dos Cubres and Pico da Esperanca.

What are holiday rentals like in Calheta?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Calheta. Holiday rentals feature extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family trip.