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Vacation rentals in São Joao

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Top-rated vacation rentals in São Joao

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A stone cottage is framed by lush greenery, overlooking the ocean. The structure features a wooden roof and expansive glass walls that provide panoramic views. The landscape includes a mix of native plants and stones, enhancing the natural setting.
Villa in São Roque do Pico
5 out of 5 average rating, 37 reviews

Casa da Canada

Would you like to live in a stone cottage, rustic, but with a modern ambiance and interior, comfortable, romantic, ideal for two with stunning views? You're in the right place, it's here. There is a deck with lounge chairs, a stone barbecue, the full view of the island of São Jorge and the canal. From its left side, the cliffs of the parishes of São Roque, Praínha and Santo Amaro do Pico, crashing waves and fluttering birds; a sunset to fall in love with… This house is part of a small family owned resort, where there is a restaurant called Magma, a grocery store, a yoga room and an heated swimming pool. The living room has glass sliding door that open the interior nature and the views. What are you waiting for?

Guest favorite
A spacious living area features a light-colored sofa and a wooden coffee table crafted from natural materials. At the back, a dining table is set, surrounded by four chairs, with a minimalist kitchen visible in the background. Large windows provide soft natural light.
Villa in Conceicao
4.94 out of 5 average rating, 17 reviews

Villa vue sur la mer et accès plage à pied

Relax in this unique and peaceful accommodation. Located in the valley of Almoxarife. 5 min walk to the most beautiful black sand beach of the island and 10 mins to the famous Horta marina and landmark downtown by car. Completely renovated, the house offers all modern comforts. All rooms have sea views. The villa "Quinta dos Maracujas" is a located on a vast orchard, where, depending on the season, you will be able to enjoy the exotic fruits. Bars and restaurants at the bottom of the street.

Top guest favorite
A charming stone house features a vibrant red door and window shutters, complemented by a balcony with modern railing. A set of steps leads to the entrance, with lush greenery visible in the background, highlighting the natural surroundings.
Villa in Pontas Negras
5 out of 5 average rating, 23 reviews

Cantinho dos Cagarros

A nossa casa de férias Cantinho dos Cagarros, com uma vista sobre o oceano Atlântico, está localizada na Aguada, Ponta Negras, na Ilha do Pico. Os quartos acolhedores proporcionam o descanso e o silêncio, que ao anoitecer é, por vezes, interrompido pelo fascinante canto dos cagarros. Desfrute da nossa varanda ou no nosso alpendre espaçoso, ideal para refeições ao ar livre com a vista do oceano. A proximidade da zona balnear "Pedreira ou Carregadouro" (a 3 minutos de distância a pé).

Guest favorite
A traditional island home features white walls and a red-tiled roof, accented by red window shutters. The house is set against a backdrop of a prominent mountain, with a clear blue sky overhead. Lush greenery surrounds the property, providing a natural setting.
Home in São Joao
4.96 out of 5 average rating, 23 reviews

PicoComigo

Conhecemos o Pico e apaixonamo-nos pela ilha. Comprámos uma casa e fomos viver na ilha. Alugamos a casa completa no 1º andar e residimos num apartamento na propriedade. Como viajantes que somos, respeitamos a privacidade dos hospedes. É uma casa tradicional da ilha, onde com todo o charme de uma casa típica do Pico, mas com todo o conforto para umas férias em família. Vista mar e montanha 300 m da zona balnear das Arinhas e com o trilho de São João a escassos 30 metros da casa.

Top guest favorite
A view of the sea framed by the open window, featuring two unique, bare trees on the shoreline. The calm water reflects the sky, while distant islands are visible on the horizon, creating a serene coastal scene.
Home in Madalena
4.95 out of 5 average rating, 205 reviews

Charming Beach House along the Ocean

Located minutes from downtown Madalena, “Casa da Barca” is a charming space granting guests picturesque views of the ocean and island of Faial from one side, and iconic Pico Mountain on the other. Walk only a few steps out the door and take a dip into natural pools or enjoy a refreshment at Pico’s award winning Cella Bar. Your host will welcome you with some cheese and wine, giving you a taste of the Acores and getting your palate ready for delicious island food.

Top guest favorite
A traditional wine house with red accents is framed by dark lava stones, set against the backdrop of Pico Mountain, topped with snow. A clear sky with a visible moon enhances the serene landscape, inviting guests to experience the uniqueness of the surroundings.
Vacation home in Madalena
4.95 out of 5 average rating, 163 reviews

Ocean view in UNESCO Heritage Site

Solar-powered wine house located in the Landscape of Pico Island Vineyard Culture - a UNESCO World Heritage Site. Just a couple of minutes driving from Madalena village, this traditional and remodeled wine house has its own vineyard on the backyard. A cozy space for two with a bedroom, kitchenette open to living room and a bathroom. The wine house is overlooking the ocean, Faial island and Pico mountain.

Superhost
A large window offers a panoramic view of the ocean and surrounding greenery. The seating area below features a cushioned bench, and soft curtains frame the view, allowing natural light to fill the space. Decorative elements are subtly placed around the area.
Home in Prainha de Cima
4.8 out of 5 average rating, 100 reviews

Fish House 3

O paraiso na terra. A vista mais bonita do mundo! Maravilhosa casa construida de raiz recentemente, situada na Prainha de Cima ( zona Norte da ilha do Pico) com vista deslumbrante sobre o canal e sobre a ilha de São Jorge. Composta por 2 pisos com 2 janelas panorâmicas, pode alojar 4 pessoas, 2 no quarto e 2 na sala em sofá-cama. Tem 2 WC's completos. Vale mesmo a pena acordar para ver o nascer do sol!

Top guest favorite
An outdoor terrace showcases a wooden dining table surrounded by four chairs. A vase filled with dried flowers sits at the center, with a backdrop of lush green hills under a clear blue sky.
Home in Ribeiras
5 out of 5 average rating, 15 reviews

Casa das Duas Ribeiras

Casa das Duas Ribeiras is a cozy Azorean house made of local lava stone, ideal for relaxing in the heart of nature on Pico Island. It offers peaceful accommodation with modern amenities, a garden and ocean views. The house is suitable for couples looking for privacy, style and the authentic atmosphere of Pico Island.

Top guest favorite
A tranquil bedroom features a spacious bed with light bedding and decorative pillows. Two woven pendant lights hang from the ceiling, providing soft illumination. A bedside table holds a lamp, and a small desk is visible against the wall, accompanied by a round mirror and a decorative plant.
Home in São Roque do Pico
4.97 out of 5 average rating, 126 reviews

Casa da Furna D'Água I

Furna D’Água I is a house with views to Pico Mountain and the island of São Jorge. The house is inserted in an old vineyard in the center of the village in the place of Cais do Pico, where the green of the vines, the black of the basalt and the aroma of the sea stand out. The ideal location for your holidays

Superhost
An outdoor dining area is set up with a wooden table and chairs, accompanied by plates and glasses. A hammock is positioned nearby, with a clear view of the mountain in the background. Green foliage surrounds the space, enhancing the serene outdoor atmosphere.
Home in São Joao
4.84 out of 5 average rating, 93 reviews

Casa do Almance - Pico, Azores

Centennial house totally remodeled in 2018. The project by an Azorean architect had the objective of maintaining the original architecture and design of the house, typical of the Azores, combining tradition with comfort and modernity. Everything has been designed to make your holiday unforgettable.

Top guest favorite
An aerial view showcases a stone house surrounded by lush greenery and terraced gardens. A private heated pool is centrally located within a well-maintained lawn, complemented by outdoor seating and parking space along a circular driveway.
Cottage in Santo Amaro - S. Roque do Pico
4.95 out of 5 average rating, 116 reviews

Casa do Caisinho Pico - Heated pool near sea

Stay in a dream lava home with a heated outdoor pool and an incredible sea view. Close to the sea, this lava house was fully restored from the ruins of a hundred-year-old lava house. We just installed the pool heating system so that, even in Winter, you can have a swim - Bliss!

Superhost
A mountain rises majestically in the background, partially obscured by clouds, with a bright sun illuminating the scene. In the foreground, a simple structure, likely used for living, is surrounded by lush greenery and tall grass.
Cottage in Bandeiras
4.8 out of 5 average rating, 123 reviews

Boanova vineyard house is a rural romantic cottage

Kick back and relax in this calm, stylish space located in Bandeiras right on hiking trails. Enjoy the natural views to the ocean or of the mountain right from the patio and if you like a good walk there are plenty of trails to explore.

Popular amenities for São Joao vacation rentals

  1. Airbnb
  2. Portugal
  3. Azores
  4. Ilha do Pico
  5. São Joao