Holiday houses in São Joao

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Top-rated holiday rentals in São Joao

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Guest favourite

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, 43 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?

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Superhost

A relaxing outdoor patio area is shown, featuring a large umbrella providing shade. A patterned rug is laid on the white surface, complemented by colorful cushions. The ocean and green hills are visible in the background under a partly cloudy sky.

Home in Horta

4.83 out of 5 average rating, 40 reviews

Cliff House | Azores splendid Ocean View

A refurbished cottage with splendid views on the South of Faial Island, 2Km from Horta. A quiet and unique setting for some memorable vacations. Only 15 minutes walk from Horta city center, close enough to visit the marina or Peters Cafe Sport by foot but far away enough to have complete privacy and stunning ocean front views. An almost 100 year old sea front house turned in to a comfortable and picturesque cottage by the sea. If you have any questions, please feel free to contact us directly.

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Guest favourite

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

4.84 out of 5 average rating, 32 reviews

PeakWithMe

We got to know Pico and fell in love with the island. We bought a house and went to live on the island. We rented the entire house on the 1st floor and lived in an apartment on the property. As travelers, we respect the privacy of our guests. It is a traditional house on the island, with all the charm of a typical Pico house, but with all the comforts for a family vacation. Sea and mountain view 300 meters from the Arinhas bathing area and with the São João trail just 30 meters from the house.

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Top Guest favourite

A charming cottage is set against the backdrop of Pico Island, featuring a red-tiled roof and blue window shutters. The property is surrounded by water, with a spacious outdoor area visible. Impressive cliffs rise in the distance, enhancing the coastal scenery.

Home in Praia do Almoxarife

4.95 out of 5 average rating, 20 reviews

Seaside Cottage

Seaside Cottage is the perfect getaway for anyone who loves the ocean. The sound of the sea is ever present in this spectacular cliff-side location, where endless views of Pico Island and the blue Atlantic soothe the senses. Enjoy early morning swims at the beach below, relax over leisurely breakfasts on the terrace and dine outside watching the stars. Horta, with restaurants, shops & activities, is just a 5 minute drive away. Well equipped & tastefully appointed, this cottage is truly unique.

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Top Guest favourite

An outdoor dining area is presented under a covered terrace, featuring a wooden table surrounded by several chairs. The view reveals a scenic coastline leading to the Atlantic Ocean, framed by rolling hills and distant mountains, illuminated by soft evening light.

Home in Santo Amaro

4.99 out of 5 average rating, 87 reviews

AtlanticWindow - Modern House, Stunning View

Pico Island, and especially Santo Amaro, has always been the holiday’s spot of our family. Here we grew up, we saw ships being built, we learnt how to swim, to fish and to live around nature. The dream of having our own place here, where to revisit the past, to rest and to enjoy the local genuine environment, has come true years later. The houses, built in a modern style, but with both inside and outside local stone details, were designed to take full advantage of the outstanding location an

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Guest favourite

An outdoor jacuzzi is positioned beneath a wooden pergola, offering panoramic views of the surrounding landscape, ocean, and distant village. The clear blue sky and scattered clouds create a tranquil atmosphere, enhancing the unique setting for relaxation.

Cabin in Madalena

4.94 out of 5 average rating, 103 reviews

Adega da Quinta - Casa do Camolas

Relax in this cottage with a unique and tranquil spot. Enjoy the fantastic view of Faial, the sea and the village of Madalena in the pool, Jacuzzi or sauna. Enjoy a beautiful wooden house in a unique and special place with a swimming pool, Jacuzzi and sauna. Benefit from the walking tours overlooking the wonderful Pico mountain. Our accommodations are located a 2-minute drive and a 20-minute walk from Vila da Madalena, and include a bedroom with a double bed and a living room with a sofa bed.

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Top Guest favourite

A terrace is showcased with two sun beds positioned for relaxation, overlooking unobstructed ocean views under a clear blue sky. The modern structure features sliding glass doors that lead inside, complementing the natural coastal environment.

Home in Ribeira Grande

4.93 out of 5 average rating, 30 reviews

Casa Oceano Pico

Casa Oceano Pico is a new, modern house nestled in one of the most beautiful and serene parts of the island, offering peace, tranquility, and lush greenery. With fabulous, unobstructed views of the Atlantic Ocean, you’ll find yourself immersed in natural beauty. Located just a 12-minute drive from the picturesque town of Lajes do Pico, and close to some of the island's most stunning natural pools, this home is ideal for solo travelers, couples, friends, families, and remote workers alike.

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Guest favourite

The interior of a wooden tent features natural wood paneling and large windows allowing views of the surrounding greenery. A spacious bed is dressed in white linens, with a light yellow throw at the foot. A kitchenette and small workspace are visible, enhancing convenience.

Tent in Horta

4.99 out of 5 average rating, 74 reviews

Azul Singular - Couple Tent

Azul Singular - Parque de Campismo Rural é o primeiro parque de Glamping dos Açores. Situado no coração de uma plantação de plantas ornamentais, na ilha do Faial, esta é a nossa versão de paraíso que queremos partilhar com quem gosta de um retiro muito ligado à Natureza. Os nossos inovadores alojamentos-tenda unem o conforto da madeira à leveza do canvas. Se não encontrar disponibilidade na nossa Couple Tent, veja as nossas outras tendas disponíveis no nosso perfil - Azul Singular.

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Guest favourite

Home in Canto da Areia

5 out of 5 average rating, 12 reviews

House by the sea

Designed from the ground up with comfort and calm in mind. With clean lines, warm materials, and wide-open views, the house invites you to slow down and soak up Pico’s natural beauty — from the private jacuzzi under the stars to the soft silence of the mornings. Whether you’re here for a romantic escape or a laid-back family adventure, this space adapts to your pace. It’s intimate, spacious, and just far enough off the map to feel like your own private piece of the island.

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Top Guest favourite

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

4.96 out of 5 average rating, 223 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.

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Guest favourite

Home in São Roque do Pico

5 out of 5 average rating, 6 reviews

Pico Sereno - Casa Montanha | Mountain View

Casa Montanha é um refúgio acolhedor e reservado na Ilha do Pico, ideal para quem procura tranquilidade e contacto com a natureza. Com uma vista privilegiada para a Montanha do Pico, combina conforto, privacidade e charme açoriano. Rodeada por vegetação, oferece um ambiente sereno para relaxar após um dia de trilhos, observação de baleias ou descoberta da ilha. O local perfeito para desacelerar, respirar fundo e criar memórias inesquecíveis.

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Superhost

A wooden interior features a large window showcasing a panoramic view of the landscape, including rolling hills and the distant mountain peak. A cozy seating area is found below the window, accompanied by two wooden tables and multiple chairs, all bathed in soft, natural light.

Home in São Roque do Pico

4.71 out of 5 average rating, 14 reviews

SKY MOUNTAIN & SEA - SMS Azores

Lots of light, amazing view over the sea and where you can see the island of São Jorge in its fullness. First line of the sea! View of Pico Mountain, the highest point in Portugal. Very comfortable house, we used wood from the island in its interior. A very good location between Madalena and São Roque and close to the Airport. Well-equipped kitchen. Relax, read, watch the sea, the boats and the Mountain too.

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