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Holiday rentals with a pool in São Mateus da Calheta

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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.
Apartment 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.

A yellow hammock is suspended between two trees, overlooking a private pool surrounded by greenery. A patio area with tables and chairs is visible in the background, along with a building featuring a tiled roof. Bright blue skies create an inviting atmosphere.
Home in Fontinhas
5 out of 5 average rating, 3 reviews

Cozy Cottage

Boasting a beautiful view of the mountain, the Country House Cozy Cottage is located in Praia da Vitória. The 80 m² property consists of a living room, a well-equipped kitchen, 2 bedrooms and 2 bathrooms as well as an additional toilet and can therefore accommodate 5 people. Additional amenities include high-speed Wi-Fi (suitable for video calls), a TV, air conditioning, a washing machine as well as a dryer. A baby cot and a high chair are also available.

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.

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 home that doesn't sacrifice comfort and refinement to be a friend of the environment. The best option for truly sustainable holidays. 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 opt for Single (1 person) or Double (2 person) and add up to 2 beds (single) ensuring space for 4 people. Breakfast is free.

A wooden structure is elevated above the ground, surrounded by lush greenery. The architecture features a cantilevered design, creating a sense of lightness. Natural elements, including trees and rocks, are visible in the foreground, enhancing the connectivity with the landscape.
Treehouse in Praia da Vitória
4.83 out of 5 average rating, 35 reviews

Lodge Floresta

Dispersés dans la végétation naturelle du complexe ils paraissent d’une légèreté extraordinaire due au fait qu’ils sont en suspension partielle par rapport au sol. Implantés dans un bosquet, isolés, ce sont de vrais observatoires de la nature. Construits avec du bois de l’ile (cryptomeria oriuda) ils présentent tous une suite double équipée avec salle de bains, table, minibar, cafetière électrique et de plus un auvent avec vue panoramique.

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

Guest favourite
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.

A panoramic view captures the serene ocean horizon, with a salt-water pool in the foreground. The expansive grassy area is bordered by low stone walls. Light blue skies with a few clouds are visible above a charming white building with a red-tiled roof.
Flat in sao barolomeu terceira
4.75 out of 5 average rating, 20 reviews

sun-apt ocean view and tranquility

Azoresresidence has 3 independent apartments. This apartment is located in the swimming pool front house with great ocean views and has a room with double bed of 140 cm and single bed, bathroom and kitchen/living room on the covered patio For those who love tranquility, privacy and peace.

Guest favourite
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.
Flat 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.

Popular amenities for São Mateus da Calheta rentals with a pool

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

  • Total holiday rentals

    Explore 20 holiday rentals in São Mateus da Calheta

  • Nightly prices starting at

    São Mateus da Calheta holiday rentals start at $141 SGD 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 holiday 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!