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Vacation 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 favorite
A large swimming pool is framed by stylish stone walls and expansive glass doors that lead into the home. Sun loungers are positioned nearby, inviting relaxation by the water. The pool reflects the sky, adding a serene touch to the outdoor space.
Home in Fonte do Bastardo
5 out of 5 average rating, 6 reviews

Casa Azul - Terceira

Welcome to Casa Azul. You will wake up to birds singing, open a window and let refreshing sea air breeze through. Unusually hot day? Enjoy the icy air conditioning. Relax by the large private pool (seasonal). Enjoy the outdoor BBQ w/sink, state of the art kitchen, wall sized movie screen, spa like bathrooms and outdoor shower/winter garden. Take a leisurely walk thru the back yard path and into the grove of fruit trees. Need to check in with the office? Use the dedicated workspace and free WiFi.

Guest favorite
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, 6 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!

Guest favorite
A spacious bedroom features a wooden platform bed with a neutral-colored blanket. Large windows allow natural light to illuminate the room, providing views of the outdoor landscape. Soft lighting is offered by wall sconces on either side of the bed.
Condo in Angra do Heroísmo
5 out of 5 average rating, 23 reviews

AngrA+ | Two bedroom apartment with sea/city view

Este Apartamento 05 - Apartamento Contemporâneo - está incluído num complexo de 6 apartamentos, o AngrA+. Tem 2 quartos e 1 sala, com uma área total de cerca de 77m2. Destaca-se pelas frentes envidraçadas sobre a cidade de Angra do Heroísmo e sobre o mar. Tem um jardim interior e espaços exteriores exclusivos com mesa e cadeiras para desfrutar da paisagem panorâmica. Localizam-se perto da zona da pool. Para uma ocupação máxima de 5 pessoas (1 cama casal, 2 camas single e 1 sofá -cama).

Guest favorite
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
4.93 out of 5 average rating, 30 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.

An indoor heated pool is featured in a spacious area with floor-to-ceiling windows allowing natural light. Comfortable lounge chairs are positioned beside the pool, with a view of the garden visible through the glass. The pool area is designed with minimalistic grey tiles.
Home in Biscoitos
5 out of 5 average rating, 4 reviews

Rocha do Mar 1

In Biscoitos, the holiday home "Rocha do Mar 1" offers an excellent view of the Atlantic. The 60 m² property consists of a living room, a fully-equipped kitchen with a dishwasher, 1 bedroom and 1 bathroom and can therefore accommodate 4 people. Additional amenities include Wi-Fi (suitable for video calls), a TV, air conditioning as well as a washing machine. A baby cot and a high chair are also available. The holiday home offers a private open terrace.

Top guest favorite
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, 23 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.

Guest favorite
A cozy room features a spacious bed with a light-colored bedspread. A red sofa with decorative buttons is positioned in front of a modern wooden dresser. Large windows with sheer curtains allow natural light to fill the space, enhancing the open layout.
Loft in Angra do Heroismo
4.98 out of 5 average rating, 49 reviews

Red House -The first impact before the immense sea

The Red House, perhaps because of its red sofa, tends to induce in those who visit us a feeling of intensity, warmth, and love. While we can't say that this house is actually more intense than the others, we do recognise that there is a mystique and that São Jorge looks different from the bathtub. Sharing the same amenities as the other houses, the Red House is the first to face the sea. This house invites you to feel happy and well.

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 favorite
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, 92 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.

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 rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    130 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool