
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.

House in Serretinha with pool & Islets view
Refúgio dos Ilhéus (RRAL 5510) is an exclusive villa in Serretinha with panoramic views over the Ilhéus das Cabras. Set across 2 floors, it features 3 air-conditioned suites (2 on the ground floor and 1 upstairs), spacious living areas, a fully equipped kitchen and a cosy reading corner. The upstairs bedroom includes a private balcony with stunning sea views. Outside, an infinity pool with a unique setting. A private and comfortable retreat, ideal for relaxing with the ocean as your backdrop.

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!

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).

Cozy Cottage
Cozy Cottage is a small guest house built on our property in a prime location, close to the island’s top attractions. This simple and welcoming space is designed so you feel at home throughout your stay. With spacious and comfortable areas, it’s perfect for relaxing and enjoying peaceful moments, whether you’re traveling with family, as a couple, or with friends. You can enjoy our large garden and outdoor pool at any time during your stay. - Pet allowed payment 10EUR per pet per night

Slow House - Azores Slowhouse
A SLOW HOME is the need to survive and find ourselves. In this house, there is the possibility of looking at the sky and looking at the sea, of looking into each other's eyes and feeling each other's heartbeat. This is a house that inspires, that slows down, that forces us to stop doing what we don't need to do and where we discover a new rhythm. Here, we assure you that a minute still has the same 60 seconds, but what fits inside is much more. It also allows us to do nothing.

Cozy cottage in Terceira Island
The Cozy Cottage is a small guest house built within our property, in a very well-located area, close to the island’s best spots. It is a simple and welcoming space designed to make you feel at home during your stay. With spacious and comfortable areas, it is ideal for resting and enjoying peaceful moments, whether you are traveling with family, as a couple, or with friends. We have a large garden and an outdoor swimming pool, that you can enjoy at any time during your stay :)

Tower House - Confort by the Sea 2456AL
House located in the parish of Cinco Ribeiras in the municipality of Angra do Heroísmo. A few meters from the sea and in one of the best bathing areas on the island. With a private pool (open year-round). With stunning views over the islands of São Jorge and Pico (South) and the largest volcano on the island of Terceira (North - Serra de Santa Bárbara). Its location allows you to watch the song of the gulls every night and occasionally see dolphins and whales.

Fisherman's House Azores
Casa rústica, inspirada no mar e na pesca. Condomínio fechado Contempla de jardim grande ao seu redor com vista para o mar, e sobre o porto de pesca de São Mateus. Também oferece espaço para refeição ao ar livre e churrasqueira. Restaurantes e cafés locais com localização próxima, a uma curta caminhada entre 5-10 minutos. Os hóspedes da casa também podem optar por cozinhar as suas próprias refeições na cozinha totalmente equipada que têm à sua disposição

Quinta Rico (AL)
Come and enjoy the Terceira Island in a calm and cozy place like Quinta Rico. Quinta Rico is a rebuilt family home, 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 heated Jacuzzi and an outdoor sauna.

Chalé d´Angra Guest House
Rodeado de natureza, e com vista constante para o seu jardim, este alojamento é o sítio ideal para a sua estadia, disponibilizando-lhe Wi-Fi gratuito, estacionamento privado, e uma zona de lazer muito apreciada com churrasqueira, forno de lenha e um amplo terraço. Situado numa zona muito calma e segura, contém uma suíte, e um quarto de casal, ambos com televisão e encontra-se completamente equipado para confecionar todo o tipo de refeições.

Red House -The first impact before the immense sea
Casa Vermelha, perhaps influenced by its red sofa, conveys to guests a sense of intensity, warmth, and love. While we cannot say it is more intense than the other houses, it does hold a certain mystique—especially when, from the bathtub, the island of São Jorge reveals itself with a unique charm. This house invites well-being, serenity, and happiness.

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
House rentals with a pool

Quinta do Paradise

Casa do Outeiro (Outeiro's House) - AL Vila Nova - Victory Beach

Rocha do Mar 1

Cantinho do Alto

Serreta View House by AzoresCollection

Sunset Pool House

Martin Guest House AZORES (Terceira Island)

Casa da Penha de França
Condo rentals with a pool

AngrA+ | Studio with terrace with sea/city view

Ocean Apartment Azores

AngrA+ | One bedroom apartment with sea/city view

AngrA+ | Studio with terrace with sea/city view
Other vacation rentals with a pool

Canto da Eira - Azores Beach House

Quinta do Abacate - Dome Garden

Yellow House - Metamorphosis in a single space

White House - Space and family comfort in nature

Quinta Rico - House II (AL)

Quinta do Abacate - Garden House (T1)

Blue House - A cosy retreat overlooking nature

Green House - Between the sea and the mountains
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