The 10 best vacation rentals in Calheta, Portugal | Booking.com
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Vacation Rentals in Calheta

Find the vacation rentals that appeal to you the most

September 2025

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The best vacation rentals in Calheta

Check out our selection of great vacation rentals in Calheta

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Abrigo da Cascata - Casas de Campo - São Jorge

Calheta

Providing garden views, Abrigo da Cascata - Casas de Campo - São Jorge in Calheta offers accommodations, a garden, barbecue facilities, and a shared lounge.

C
Carvalho
From
Portugal
Anita was absolutely amazing, she was our private chef for our stay as we were the only ones there at the time of our booking. We had wonderful conversations with her and could have chatted the whole time we were there. The meals were exceptional, fit for a king. Sylvia the property manager was very delightful and made our stay so comfortable, we also could have chatted with her for our entire stay. She was very helpful in telling us what to do and see, which we enjoyed fully.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 177 reviews
Price from
$194.68
1 night, 2 adults
Check availability

Kuanza Nature Experience, Fajã do Belo

Fajã da Caldeira de Santo Cristo (Near Calheta)

Offering garden views, Kuanza Nature Experience, Fajã do Belo in Fajã da Caldeira de Santo Cristo offers accommodations, a private beach area, an outdoor swimming pool, a garden, and barbecue...

E
Elsa
From
Canada
The location is beautiful and the hosts are amazing.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 159 reviews
Price from
$123.14
1 night, 2 adults
Check availability

Caldeira Guesthouse

Fajã da Caldeira de Santo Cristo (Near Calheta)

Caldeira Guesthouse features rooms in Fajã da Caldeira de Santo Cristo. This beachfront property offers access to a balcony and free Wifi.

S
Sanjay
From
Germany
Beautiful location, and amazing hospitality! Great food!
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 264 reviews
Price from
$58.64
1 night, 2 adults
Check availability

Casa da Eira Velha

Fajã do Ouvidor (Near Calheta)

Featuring a garden, Casa da Eira Velha features accommodations in Fajã do Ouvidor. This property offers access to a patio, free private parking, and free Wifi.

J
Joe
From
Canada
The owners were very communicative and responsive. The place is very cozy and perfect for us as a couple travelling alone. Great patio with hammocks and very well thought out inclusions in the home.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 34 reviews
Price from
$99.69
1 night, 2 adults
Check availability

Casa Grão de Café AL

Fajã dos Vimes (Near Calheta)

Featuring barbecue facilities, Casa Grão de Café AL features accommodations in Fajã dos Vimes. Guests can benefit from a patio and an outdoor fireplace.

C
Cyndy
From
United States
Super location, clean, welcoming
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 44 reviews
Price from
$172.64
1 night, 2 adults
Check availability

Casa D´Arminda

Norte Pequeno (Near Calheta)

This property offers access to a patio and free private parking. This vacation home includes 3 bedrooms, a living room and a flat-screen TV, an equipped kitchen with a dining area, and 1 bathroom with...

D
Drew
From
United States
Pleasant location right in the middle of Norte Pequeno. Easy access to food and drink. The host was quick and willing to provide us with vinegar baking soda solution to kill mold in the bathroom.
Scored out of 10, guest rating 7.5
Good - What previous guests thought, 16 reviews
Price from
$73.89
1 night, 2 adults
Check availability

Casa dos Lagos - RRAL nº 2187

Velas (Near Calheta)

Offering mountain views, Casa dos Lagos - RRAL nº 2187 in Velas features accommodations and a garden. This apartment provides air-conditioned accommodations with a patio.

C
Carmina
From
United States
Our stay at Casa dos Lagos couldn't have gone better. Leodora messaged us before our checkin to make sure we understood the instructions and offered to answer our questions. She also checked on us a few times via Whatsapp during our stay to make sure we had what we needed. The apartment was so comfortable and clean. There's a stove, microwave, electric kettle, small refrigerator and espresso machine in the kitchen. There was plenty of space in the whole apartment, and the air conditioning worked great. The bathroom was very clean. It was also a very comfortable bed, with nice bedding and comforter. And the best part was the unmatched views from the balcony. We were able to drive into town to get some groceries and made use of the kitchen a few times during our stay. They provide enough kitchenware, plates, silverware, etc., to make use of it. Dinner at sunset on the balcony is one of the best memories I take with me from this trip. Even Mt. Pico cooperated and graced us with a view of its peak a few times during our stay. We were very grateful for the available laundry machine in the reception area - they provide drying racks and detergent. It was very needed by this point in our whole trip, so we were relieved to be able to have this option. Also, the location was great - in addition to the amazing views, it was a very short 3-min drive into town (Velas) where there are stores and restaurants to choose from. The ferry is also accessible from Velas, which allowed us to take a day trip to Pico. This place was truly a great value.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 230 reviews
Price from
$152.46
1 night, 2 adults
Check availability

Tropical Fruit Garden

Velas (Near Calheta)

Featuring garden views, Tropical Fruit Garden in Velas features accommodations and a garden. There's a sun terrace and guests can access free Wifi and free private parking.

A
Anne
From
Canada
The fresh fruit and greens! The passionate owners/gardeners. Having a washing machine.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 118 reviews
Price from
$35.18
1 night, 2 adults
Check availability

Casa de São João

Fajã de São João (Near Calheta)

Offering a garden, Casa de São João offers accommodations in Fajã de São João. Both free Wifi and parking on-site are accessible at the vacation home free of charge.

S
Stephanie
From
United States
Beautiful views and well appointed to relax after exploring the island. The home is located in one of the Fajas, about 10 minutes from the main road. Paula was very helpful during our stay. The views from the balcony area were amazing!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 20 reviews
Price from
$177.33
1 night, 2 adults
Check availability

Quinta da Magnólia AR

Urzelina (Near Calheta)

Featuring garden views, Quinta da Magnólia AR in Urzelina provides accommodations and a garden. There's a private entrance at the farm stay for the convenience of those who stay.

D
Donna
From
Canada
This is a high quality beautiful location. Very convenient location, easy free parking, great breakfasts and spectacular pool.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 119 reviews
Price from
$133.70
1 night, 2 adults
Check availability
All vacation rentals in Calheta

Most booked vacation rentals in Calheta and surrounding area in the past month

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These vacation rentals in Calheta and nearby have options with free cancellation

  • Casa Grão de Café AL

    Fajã dos Vimes
    Free cancellation options available
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 44 reviews

    Featuring barbecue facilities, Casa Grão de Café AL features accommodations in Fajã dos Vimes. Guests can benefit from a patio and an outdoor fireplace.

  • Caldeira Guesthouse

    Fajã da Caldeira de Santo Cristo
    Free cancellation options available
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 264 reviews

    Caldeira Guesthouse features rooms in Fajã da Caldeira de Santo Cristo. This beachfront property offers access to a balcony and free Wifi.

  • Adega Vermont

    Biscoitos
    Free cancellation options available
    Scored out of 10, guest rating 8.5
    Very Good - What previous guests thought, 32 reviews

    With garden views, this accommodation offers a patio. The chalet provides parking on-site, a solarium, and a 24-hour front desk.

  • Adega Jaquet

    Biscoitos
    Free cancellation options available
    Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 36 reviews

    Offering a garden, Adega Jaquet provides accommodations in Biscoitos. This chalet offers accommodations with a terrace. The chalet is composed of 1 bedroom, a fully equipped kitchen, and 1 bathroom.

  • Casa D´Arminda

    Norte Pequeno
    Free cancellation options available
    Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 16 reviews

    This property offers access to a patio and free private parking. This vacation home includes 3 bedrooms, a living room and a flat-screen TV, an equipped kitchen with a dining area, and 1 bathroom...

  • Casas Dos Vimes

    Fajã dos Vimes
    Free cancellation options available
    Scored out of 10, guest rating 9.4
    Wonderful - What previous guests thought, 75 reviews

    Providing barbecue facilities, Casas Dos Vimes offers accommodations in Fajã dos Vimes. With sea views, this accommodation features a patio.

  • Casa do Zé - AL

    Manadas
    Free cancellation options available
    Scored out of 10, guest rating 8.8
    Excellent - What previous guests thought, 50 reviews

    Offering mountain views, Casa do Zé - AL in Manadas offers accommodations and a garden. Both free Wifi and parking on-site are available at the country house free of charge.

  • Quinta do Caminho da Igreja TER-Casas de Campo

    Velas
    Free cancellation options available
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 30 reviews

    Providing inner courtyard views, Quinta do Caminho da Igreja TER-Casas de Campo in Velas offers accommodations, a garden, and a shared lounge.

Enjoy breakfast in Calheta and nearby

  • Casa do Zé II AL

    Velas
    Breakfast options
    Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 69 reviews

    Providing garden views, Casa do Zé II AL in Velas provides accommodations, a garden, and barbecue facilities. There's a private entrance at the apartment for the convenience of those who stay.

  • Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 15 reviews

    Offering a garden, Casa da Lagoa AL 416 features accommodations in Fajã da Caldeira de Santo Cristo. With sea views, this accommodation offers a terrace. The vacation home provides a shared lounge.

  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 7 reviews

    This property offers a private pool and free private parking. The vacation home is composed of 3 bedrooms, a fully equipped kitchen, and 1 bathroom.

  • Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 34 reviews

    Featuring a garden, Casa da Eira Velha features accommodations in Fajã do Ouvidor. This property offers access to a patio, free private parking, and free Wifi.

  • Scored out of 10, guest rating 9.9
    Exceptional - What previous guests thought, 52 reviews

    Featuring mountain views, Houses of Eira Velha in Fajã do Ouvidor features accommodations, a garden, and barbecue facilities.

  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 211 reviews

    Offering a garden, São Jorge Spot - Alojamento provides accommodations in Velas. This beachfront property offers access to a patio, free private parking, and free Wifi. Guests can use a terrace.

  • Retiro Atlântico

    Urzelina
    Breakfast options
    Scored out of 10, guest rating 9.4
    Wonderful - What previous guests thought, 103 reviews

    Providing a garden, Retiro Atlântico provides accommodations in Urzelina. This property offers access to a terrace, free private parking, and free Wifi. Guests can use barbecue facilities.

Highly rated vacation rentals in Calheta and nearby

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 159 reviews

    Offering garden views, Kuanza Nature Experience, Fajã do Belo in Fajã da Caldeira de Santo Cristo offers accommodations, a private beach area, an outdoor swimming pool, a garden, and barbecue...

    From $316.66 per night

Research, refine, and make plans for your whole trip

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