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Vacation rentals in São Joao

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Top-rated vacation rentals in São Joao

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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 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

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.

Guest favorite
A glass of red wine is positioned on a white surface, overlooking a green landscape and the ocean. The distant outline of a neighboring island is visible against a partly cloudy sky, providing a serene view of Pico Island's natural beauty.
Home in São Roque do Pico
5 out of 5 average rating, 29 reviews

~The View Of The Blue~

Nestled up on a charming hilltop with stunning panoramic views, you cannot go wrong with this guesthouse. The View of The Blue is the space that appeals to all of your senses & to truly relax & take in the many natural wonders that Pico Island offers. Located 5kms from São Roque centre & ferry terminal,offering shops/restaurants/bakeries/cafes/museums/natural ocean pools & a starting point to Mt. Pico road&elsewhere. Private & Spacious Home. Value & Tranquility. Take A View & See You Soon.

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 charming exterior view showcases a two-story house with a balcony, surrounded by lush greenery and colorful flowering plants in terracotta pots. A stone pathway leads up to the entrance, offering glimpses of the natural landscape and distant hills.
Home in Santo Amaro
4.96 out of 5 average rating, 85 reviews

House of the Black Cat

Located in a quiet area of the parish of Santo Amaro, where you wake up in the middle of nature with a fantastic view of the sea and São Jorge Island. Behind are the slopes of the northern part of the island. About 200 meters away is the Portinho bathing area. The house is equipped with a flat-screen TV with cable channels, air-conditioning and Wi-Fi. It has a bedroom/living room with a double bed, a bathroom and a kitchen.

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

Seagull Corner

Our holiday home Cantinho dos Cagarros, overlooking the Atlantic Ocean, is located in Aguada, Ponta Negras, on the island of Pico. The cozy rooms provide rest and silence, which at dusk is sometimes interrupted by the fascinating song of the gulls. Enjoy our balcony or our spacious porch, ideal for outdoor dining with ocean views. The proximity of the "Pedreira or Carregadouro" bathing area (a 3-minute walk away).

Top guest favorite
A kitchen area is presented with wooden cabinets and a dining table surrounded by four chairs. The geometric-patterned wallpaper adds a modern touch, while stainless steel appliances include a refrigerator. A staircase with wooden steps leads to the upper level.
Home in Madalena
4.95 out of 5 average rating, 117 reviews

Grandfather Francisco's House

Once a traditional wine cellar, built by Francisco Paulo in 1980, this villa served for many years as a production site and warehouse for the Paulo family's wine. The wine cellar has been remodeled and expanded, but it maintains the traditional elevations and the decoration and details of the times when it was used as a wine cellar. Next to the bathing area, it has a view that invites long nights of conversation.

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
4.79 out of 5 average rating, 101 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!

Superhost
A two-story house with a white exterior and red window accents is set against a lush green landscape. The structure features a traditional tiled roof and is framed by natural foliage, with a backdrop of a mountain rising into the sky.
Home in São Joao
4.72 out of 5 average rating, 36 reviews

House with a view of the bay

Casa Vista Baia offers accommodations in the parish of São João Pico. This holiday home is located in a private secluded area on the coastal side with ocean views and the beautiful Mountain Peak above. Ponta do Admoiro is close to picnic areas with small natural pools and a natural area for swimming. Two more natural pools located Nearby. During the summer, there is a food and drink bar.

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

House of the Two Rivers

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 (House of 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

Popular amenities for São Joao vacation rentals

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