Calheta Holiday Rentals

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Holiday Rentals in Calheta

Matilde's House, in the paradise Fajã de São João

Santo Antão, São Jorge
9.0 out of 10, Wonderful, (6)
"Haus ist etwas dunkel, aber ansonsten sehr gut eingerichtet und sauber. Blick von der Terrasse aufs Meer und auf die Insel Pico. Wer Katzen mag, ist hier sehr gut aufgehoben."
Germany
Thomas P.
Matilde's House, in the paradise Fajã de São João

Herdade das Hortênsias

São Jorge
10.0 out of 10, Exceptional, (1)
"Ruhig gelegen mit genügend Platz."
Germany
Lukas R.
The price is AU$205
includes taxes & fees
5 Dec - 6 Dec
Herdade das Hortênsias

Fajã da Caldeira House - AL

Ribeira Seca - São Jorge - Açores
10.0 out of 10, Exceptional, (1)
"A fajã da Caldeira de Santo Cristo é um dos lugares de visita obrigatório em S. Jorge. Embora não tenha acesso de carro, existem dois trilhos que permitem o acesso ao lugar. Fizemos o trilho mais pequeno e demorámos aproximadamente 1 hora (levávamos crianças connosco). Alternativamente, este trilho pode ser feito com moto4. Vários habitantes locais fornecem esse serviço aos turistas para facilitar a entrada e saída da fajã. O nosso anfitrião (o Miguel), também se disponiblizou para nos facilitar...
Portugal
José S.
Fajã da Caldeira House - AL

Aldeia das Adegas

4.0 star property
Sao Roque do Pico
9.4 out of 10, Exceptional, (63)
"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$177
includes taxes & fees
2 Jan - 3 Jan 2026
Aldeia das Adegas

Casa do Zé - AL

3.0 star property
Velas
9.4 out of 10, Exceptional, (6)
"Adorable local cottage in a very small town. We stayed in the 2 bedroom apartment on the second floor. Neighbors gave us a walking tour and showed us their garden and taught us history of the area. "
United States
Susan
Casa do Zé - AL

Panoramic Ocean Views from your Private Varand

São Roque do Pico
The price is AU$280
includes taxes & fees
17 Dec - 18 Dec
Panoramic Ocean Views from your Private Varand

Adegas do Pico

4.0 star property
Sao Roque do Pico
9.0 out of 10, Wonderful, (38)
"Very nice rural property "
United States
Mario
Adegas do Pico

AtlanticWindow - Modern House, Stunning View

São Roque do Pico
10.0 out of 10, Exceptional, (49)
"The house was very comfortable for 4 adults and had everything needed for a great stay. The view is spectacular. Helena was very accommodating. I would recommend AtlanticWindow for anyone looking to stay on Pico for a few days. "
Portugal
Doyle B.
AtlanticWindow - Modern House, Stunning View

Pike Cliffs - Amazing view to S. Jorge

Prainha de Cima
9.6 out of 10, Exceptional, (8)
"We stayed at Pike Cliffs in July. The house is lovely and suitable for 4-6 people. We really like the views, and were able to reach Francisco when we got lost getting to the place. Thank you Francisco!"
Canada
A C.
Pike Cliffs - Amazing view to S. Jorge

4 bedrooms & great view

Sao Roque do Pico, Azores
9.8 out of 10, Exceptional, (9)
"The check-in was a breeze and the house has everything you need to stay in and cook and there’s always a nice breeze to keep the house cool "
United States
Steven C.
4 bedrooms & great view

A Casa do Ouvidor

4.0 star property
Sao Roque do Pico
9.8 out of 10, Exceptional, (29)
"Asan was a great host. Quiet place, very roomy and clean, the view is amazing. Every thing was in place to enjoy a confortable stay. "
Canada
Sébastien
A Casa do Ouvidor

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

Lajes do Pico
8.8 out of 10, Excellent, (5)
"Lovely place, very beautiful and calm, also very clean. Isa is a very nice and extremely helpful host. Absolutely recommend to stay here!"
Austria
Lara Sophie S.
Casa Céu D'Abraão - You can click to enlarge the photo

Faidoca's Grandfather House - Four-Bedroom House

Calheta de Nesquim
10.0 out of 10, Exceptional, (20)
"It was a wonderful place and our host was a beautiful caring lady."
Canada
Liz S.
Faidoca's Grandfather House - Four-Bedroom House

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

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

Cagarra Nest Winery

Lajes do Pico Açores
10.0 out of 10, Exceptional, (8)
"Beautiful view and sounds of the ocean waves. A short walk to the ocean."
United States
Gillian B.
Cagarra Nest Winery

Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".

Santo Amaro, Sao Roque, Ilha do Pico, Azores
10.0 out of 10, Exceptional, (24)
"Wonderful little house with amazing views and terrific host. Perfect for couples get away. You will love the true Pico Island experience here. "
United States
Austin
Enchanting view from the balcony of beautifully restored "Adega Baia do Canto".

Adega Velha holiday home, next to the sea and mountains, ideal for couples

Calheta de Nesquim
9.8 out of 10, Exceptional, (21)
"Adega Velha was a perfect place for the two of us while we explored Pico. Although it is a very small house, it was impeccably clean, comfortable and beautifully appointed. Everything you could imagine needing was there, tidily tucked in to its own appointed space. The view from the house is exceptional, and we found the quiet location so charming and restful. Fatima and her husband were extremely gracious, even leaving us a gift basket upon our arrival. I highly recommend this guest house and...
Portugal
Seward O.
Adega Velha holiday home, next to the sea and mountains, ideal for couples

Houses In Pico

3.0 star property
Sao Roque do Pico
8.6 out of 10, Excellent, (13)
"Pleasant surprise with gift basket and heater on at arrival! We never saw the host, but very accommodating online. Well equipped and nice location. On the downside, the beds and pillows are very hard."
Norway
Vibeke
Houses In Pico

Casas da Junqueira

4.0 star property
Sao Roque do Pico
9.2 out of 10, Wonderful, (12)
"A clean modern apartment. Bed was comfortable with nice sheets and pillows. Kitchen had basic cooking utensils but unfortunately not have basic items for cooking like salt, pepper, sugar, oil. Nice welcome basket of goodies was much appreciated."
Canada
Lorne
Casas da Junqueira

Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar

São Roque do Pico
Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar
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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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$177 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.

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.