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Vacation rentals with a pool in São Mateus da Calheta

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in São Mateus da Calheta

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite
A modern, elevated villa is surrounded by lush greenery, featuring a sloped roof and a small balcony with seating. The structure is set amidst various plants, emphasizing its integration with nature. A rocky landscape complements the natural setting.
Farm stay in Biscoitos
5 out of 5 average rating, 8 reviews

Casas do Morgadio

“CASAS DO MORGADIO – azorean wine and lodge” are located in Biscoitos, a land with a long tradition in wine production. It is part of a family property with about 2.5 hectares that still maintains all its functional structure (houses, agricultural fields, winery and distillary) and where the vine and other fruit trees are grown, wine and brandy are produced, for at least three generations. We are a Farm Tourism, with 4 accommodation units, onebedroom villas. Visit our refuge close to nature!

Top guest favourite
A spacious studio is framed by a prominent stone archway. The room features warm wooden flooring and soft, neutral-toned walls. A well-made bed with light linens and accent pillows is visible, along with a window that brings in natural light.
Condo in Angra do Heroísmo
4.98 out of 5 average rating, 46 reviews

AngrA+ | Studio with terrace with sea/city view

Este Apartamento 01 - Apartamento do Arco - está incluído num complexo de 6 apartamentos, o AngrA+. É um estúdio (T0), térreo e apropriado para mobilidade reduzida. Tem 40m2 e é dominado por um arco em cantaria do séc. XVII. Tem uma ampla (17m2) varanda exclusiva com mesa/cadeiras e com vista sobre o jardim, a cidade e o mar. Para uma ocupação máxima de 2 pessoas. Os espaços comuns incluem o jardim, uma pool exterior, uma esplanada e um salão com biblioteca e lareira.

Guest favourite
An outdoor area features a large swimming pool surrounded by lounge chairs under clear skies. The house, with a blue and white facade, is visible in the background, alongside a spa area and green landscaping that enhances the serene environment.
Home in Quatro Ribeiras
4.94 out of 5 average rating, 32 reviews

Quinta Rico - House II (AL)

Come and enjoy the Terceira Island in a calm and cozy place like Quinta Rico. Quinta Rico - House II is a new house built from scratch, with all the amenities and a privileged view of the sea. You can stroll through its orchards where you can find a variety of fruit trees, as well as small vegetable gardens and some animals such as chickens, peacocks, turkeys and rabbits. Guests have access to a generous swimming pool with a heated Jacuzzi and an outdoor sauna.

Superhost
A spacious room features a large bed with yellow pillows and an orange blanket. Natural light enters through a large glass door leading to a private outdoor seating area, where two wooden chairs are visible. Neutral colors and sleek tile flooring complete the design.
Place to stay in Angra do Heroísmo
4.93 out of 5 average rating, 14 reviews

Quinta do Abacate - Garden House (T1)

A house that does not sacrifice comfort and refinement to be environmentally friendly. The best option for a truly sustainable holiday. It has an area of 51.38 m2, with a kitchen, living room, bed room (Queen), and bathroom, there is the possibility of adding 2 extra beds, thus allowing capacity for up to 4 people. You can choose either Single (1 person) or Double (2 people) and add up to 2 (single) beds, guaranteeing space for 4 people. Breakfast is free.

Guest favourite
A cozy interior space features a spacious bed with a light-colored covering, positioned nearby a modern green sofa accented with decorative pillows. A wooden dresser stands in the background, while sheer curtains allow natural light to brighten the room.
Loft in Angra do Heroísmo
4.89 out of 5 average rating, 45 reviews

Green House - Between the sea and the mountains

From the Green House, you can see São Jorge, Pico and Graciosa. The three neighbouring islands bear witness to the time our guests spend gazing at them. They are vain and like to be admired. They are uninhibited, exposing themselves to those who want to see them. The Green House, situated in the middle of the farm, is a balancing point between the different views. From its windows, you can see the sea, the mountains, the cerrados and Pico da Vigia.

Top guest favourite
A private pool is surrounded by a spacious deck, featuring bright blue water under a clear sky. A modern tower structure is visible in the background, framed by a red-tiled roof and greenery.
Villa in Angra do Heroísmo
5 out of 5 average rating, 25 reviews

Tower House - Confort by the Sea 2456AL

Casa situada na freguesia das Cinco Ribeiras do Concelho de Angra do Heroísmo. A poucos metros do mar e numa das melhores zonas balneares da ilha. Com piscina privada (aberta todo o ano). Com vista deslumbrante sobre as ilhas de São Jorge e Pico (Sul) e do maior vulcão da ilha Terceira (Norte - Serra de Santa Bárbara). A sua localização permite assistir todas as noites ao cantar dos cagarros e ver esporadicamente golfinhos e baleias.

A charming exterior features a cobblestone pathway leading to a rustic stone house, illuminated softly by warm lighting. Red wooden wheels and various ceramic pots are displayed on either side, surrounded by lush greenery and an inviting atmosphere, accentuated by the night sky.
Home in Porto Martins
4.83 out of 5 average rating, 12 reviews

Quinta do Paradise

Quinta do Paraíso is an ideal place for a well-deserved rest or a good family vacation, it is a private place where you can enjoy several spaces to relax reading a good book, or enjoy a beautiful landscape facing the sea. It's a place with olive trees and some pets, a pool, and BBQ area. In the house, the living room has a salamander, full kitchen, bathroom with bath, bedroom with extra bed and possibility of installing a baby crib

Superhost
An aerial view reveals a coastal neighborhood surrounded by lush green fields, leading to the ocean. A natural blue pool is visible amidst gardens, with several homes arranged harmoniously along the winding road. In the background, the Ilhéus das Cabras islands rise from the sea.
Villa in Açores
4.89 out of 5 average rating, 36 reviews

Canto da Eira - Azores Beach House

Ten minutes from Angra do Heroísmo, Canto da Eira is located in Serretinha, the sunniest spot on Ilha Terceira and facing Ilhéus das Cabras. A 5-minute drive away you will find three beaches and natural ocean pools with access stairs and support infrastructure. Located between the parish of Porto Judeu and Feteira, you'll find in the local shops and good restaurants, the perfect support for your stay.

Guest favourite
A tranquil outdoor space is showcased, featuring a saltwater pool that glimmers under clear skies. A hammock is positioned nearby, offering a relaxing view of the pool and the ocean beyond. Colorful lounge chairs are arranged around the pool, enhancing the inviting atmosphere.
Apartment in São Bartolomeu
4.85 out of 5 average rating, 26 reviews

ocean view and tranquility Butterfly-Apt.

Azoresresidence has 3 independent apartments. This apartment is located in the swimming pool front house with great ocean views and has a double bedroom and sofa bed in the kitchen, bathroom and large kitchen/living room and covered patio. For those who love tranquility, privacy and peace.

The modern exterior features expansive glass sliding doors that open to a spacious interior. A wooden deck surrounds the clear pool, complemented by white lounge chairs and a small table. The design emphasizes a seamless connection between indoor and outdoor living spaces.
Apartment in Angra do Heroísmo
4.86 out of 5 average rating, 44 reviews

Ocean House incredible view Azores

Picturesque house to make the delights of sea lovers, with 2 suites, equipped kitchen, and a stunning living room with balcony to access the garden and pool that is lost on the horizon. Enjoy in the garden of the fantastic sunset with the islands São Jorge and Pico as a backdrop.

Superhost
The outdoor swimming pool area is complemented by two thatched umbrellas providing shade. Four lounge chairs, alternating in color, are positioned beside the pool, inviting relaxation. A lush garden area with palm trees and hydrangeas is visible in the background, enhancing the serene environment.
Guesthouse in Praia da Vitória
4.76 out of 5 average rating, 93 reviews

Cozy cottage in Terceira Island

The cozy cottage is a small guest house that we build in our property. Our property is very well located close to the best spots in the island. We have a charming garden and wonderful swimming pool. We have two dogs called Zara and Ariel.

Top guest favourite
A serene outdoor pool reflects the vibrant colors of a sunset over the ocean. The horizon is framed by lush greenery, while the sky transitions from blue to warm orange and pink hues, creating a calm and inviting atmosphere.
Cottage in Angra do Heroísmo
4.98 out of 5 average rating, 55 reviews

Quinta do Morcego, a refuge in nature!

Ideal retreat, in the parish of Serreta, to rest, with privacy and full contact with nature.

Popular amenities for São Mateus da Calheta rentals with a pool

Quick stats about vacation rentals with a pool in São Mateus da Calheta

  • Total vacation rentals

    Explore 20 vacation rentals in São Mateus da Calheta

  • Nightly prices starting at

    São Mateus da Calheta vacation rentals start at $154 CAD per night before taxes and fees

  • Verified guest reviews

    Over 130 verified reviews to help you choose

  • Wifi availability

    20 of São Mateus da Calheta vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across São Mateus da Calheta rentals

  • 4.9 Average rating

    São Mateus da Calheta stays are highly rated by guests—averaging 4.9 out of 5!