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

Beach
Herdade das Hortênsias

Holiday Home in São Jorge

10.0 out of 10, Exceptional, (1)
"Ruhig gelegen mit genügend Platz."
Germany
Lukas R.
The price is HK$688
HK$1,032 total
includes taxes & fees
6 Dec - 7 Dec
Herdade das Hortênsias
Outdoor pool
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)

Holiday Home in São Jorge

10.0 out of 10, Exceptional, (1)
"serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso."
Portugal
Pedro E.
The price is HK$1,763
HK$1,980 total
includes taxes & fees
14 Dec - 15 Dec
Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista)
Terrace/patio
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi

Apartment in Topo Calheta São Jorge Açores

The price is HK$863
HK$863 total
includes taxes & fees
4 Dec - 5 Dec
Apartment 'Moradia Machado' with Private Terrace, Balcony and Wi-Fi
Outdoor pool
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)

Holiday Home in São Jorge

The price is HK$1,763
HK$1,962 total
includes taxes & fees
4 Dec - 5 Dec
Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto)
Outdoor pool
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)

Holiday Home in Calheta

The price is HK$1,284
HK$1,498 total
includes taxes & fees
7 Dec - 8 Dec
Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua)
Outdoor pool
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)

Holiday Home in São Jorge

The price is HK$1,157
HK$1,320 total
includes taxes & fees
7 Dec - 8 Dec
Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro)
Outdoor pool
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)

Holiday Home in São Jorge

10.0 out of 10, Exceptional, (4)
"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 HK$1,880
HK$2,118 total
includes taxes & fees
10 Dec - 11 Dec
Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf)
Outdoor pool
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba

Holiday Home in São Jorge

The price is HK$1,672
HK$1,889 total
includes taxes & fees
10 Dec - 11 Dec
Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba
Exterior
Aldeia das Adegas

Apartment in Sao Roque do Pico

4.0 star property
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
Exterior
Casa dos Felicias

Holiday Home in São Roque do Pico

10.0 out of 10, Exceptional, (1)
"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 HK$678
HK$1,383 total
includes taxes & fees
6 Dec - 7 Dec
Casa dos Felicias
Property grounds
Vila Paim - Apart. Low

Holiday Home in São Roque do Pico

10.0 out of 10, Exceptional, (1)
"Great getaway super quiet and very relaxing place."
United States
Joe F.
The price is HK$407
HK$1,383 total
includes taxes & fees
6 Dec - 7 Dec
Vila Paim - Apart. Low
Fridge, microwave, oven, stovetop
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi

Villa in Lajes do Pico

The price is HK$441
HK$441 total
includes taxes & fees
12 Dec - 13 Dec
Villa 'Casa Ponta Do Biscoito' with Sea View, Private Garden and Wi-Fi
Private kitchen
Silveira House

Holiday Home in Lajes do Pico

The price is HK$407
HK$796 total
includes taxes & fees
10 Dec - 11 Dec
Silveira House
2 bedrooms, iron/ironing board, WiFi, bed sheets
Adega do Mirante

Holiday Home in São Roque do Pico

8.0 out of 10, Very good, (1)
"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 HK$678
HK$1,383 total
includes taxes & fees
20 Dec - 21 Dec
Adega do Mirante
TV
Holiday Home 'Adega Pérola' with Wi-Fi

Holiday Home in Cais do Galego

The price is HK$744
HK$1,295 total
includes taxes & fees
5 Dec - 6 Dec
Holiday Home 'Adega Pérola' with Wi-Fi
Outdoor dining
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi

Holiday Home in Engrade

10.0 out of 10, Exceptional, (1)
"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 HK$1,985
HK$1,985 total
includes taxes & fees
15 Dec - 16 Dec
Vacation Home "Adega Do Portinho Velho" with Balcony & Wi-Fi
Property grounds
Amazing One Bedroom Apartment with Sea View

Apartment in São Roque do Pico

The price is HK$723
HK$723 total
includes taxes & fees
4 Dec - 5 Dec
Amazing One Bedroom Apartment with Sea View
1 bedroom
Very well equipped apartment in the center of São Roque do Pico

Holiday Home in 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 HK$814
HK$1,654 total
includes taxes & fees
23 Dec - 24 Dec
Very well equipped apartment in the center of São Roque do Pico
Microwave, oven, stovetop, dishwasher
Panoramic Ocean Views from your Private Varand

Holiday Home in São Roque do Pico

The price is HK$1,116
HK$1,414 total
includes taxes & fees
12 Dec - 13 Dec
Panoramic Ocean Views from your Private Varand
Fridge, microwave, oven, stovetop
Vacation Home "Casas Dos Vinagreiros - Pedro" with Sea View, Private Terrace & Wi-Fi

Holiday Home in Pontas negras

The price is HK$2,084
HK$2,470 total
includes taxes & fees
9 Dec - 10 Dec
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.
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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:

  • View our selection of featured holiday rentals in Calheta
  • Use the map to find apartments and other holiday homes in the Calheta neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Calheta while they last

Look no further and take a look at our great range of rental properties in Calheta!

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.