Calheta Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Calheta

Fridge, microwave, oven, stovetop
Matilde's House, in the paradise Fajã de São João

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
Beach
Herdade das Hortênsias

Herdade das Hortênsias

São Jorge
10.0 out of 10, Exceptional, (1)
"Ruhig gelegen mit genügend Platz."
Germany
Lukas R.
The price is HK$687
HK$1,031 total
includes taxes & fees
10 Dec - 11 Dec
Herdade das Hortênsias
Property grounds
Fajã da Caldeira House - AL

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
Exterior
Aldeia das Adegas

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 HK$869
HK$904 total
includes taxes & fees
2 Jan - 3 Jan 2026
Aldeia das Adegas
View from property
Casa do Zé - AL

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
Microwave, oven, stovetop, dishwasher
Panoramic Ocean Views from your Private Varand

Panoramic Ocean Views from your Private Varand

São Roque do Pico
The price is HK$1,116
HK$1,414 total
includes taxes & fees
4 Dec - 5 Dec
Panoramic Ocean Views from your Private Varand
Terrace/patio
Adegas do Pico

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
Smart TV, DVD player, books
AtlanticWindow - Modern House, Stunning View

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
Interior
Pike Cliffs - Amazing view to S. Jorge

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
TV, fireplace
4 bedrooms & great view

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
Outdoor pool
A Casa do Ouvidor

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
Exterior
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
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
Property grounds
Faidoca's Grandfather House - Four-Bedroom House

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

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

Ribeirinha
New Family Home with a View of São Jorge Island – Ribeirinha
Outdoor dining
Cagarra Nest Winery

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
Property grounds
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
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".
Terrace/patio
Adega Velha holiday home, next to the sea and mountains, ideal for couples

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
Front of property
Houses In Pico

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
Living room
Casas da Junqueira

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
1 bedroom, iron/ironing board, WiFi, bed sheets
Pico Blue Ocean – Elegant Oceanfront Escape on Avenida do Mar

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

Casa do Zé - AL

Casa do Zé - AL

10/10 Excellent
"The Casa do Ze is very well equipped with all utensils and essentials for cooking your own meals. The coffee maker is a moka pot, (first time using one) that makes great espresso. Bathroom supplies are also provided. The Casa is located at the end of a street and is a renovated old home, so it's more authentic than some other stays. The communication with the owner was excelent. WiFi was OK but sometimes cut out. Also, hot water supply was finicky as sometimes there would be plenty and other times none."
Lorne 5-night trip
Posted 1 month ago
Casa do Zé - AL

Find out more about Calheta

Search for holiday rentals in Calheta on Expedia! You can easily find your home rentals, villas, holiday apartments in Calheta using one of the methods below:

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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.