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Holiday rentals in Prainha

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Top-rated holiday rentals in Prainha

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

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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
5 out of 5 average rating, 36 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 favourite
A dining area is set by the sea, featuring a wooden table with elegant glassware and plates arranged neatly. Comfortable chairs are positioned around the table, offering a scenic view of the ocean and distant land. The calm water reflects a serene atmosphere.
Home
4.98 out of 5 average rating, 57 reviews

Janela do Porto - the Atlantic Ocean inside the house

A window facing the sea and back on the slopes of the north coast of Pico Island. Sitting in the armchair, I set my gaze on São Jorge lying in the distance. At the foot of the house, the sea ripples like a purring cat. I close my eyes and smile, I found paradise... Old fishing cellar completely rebuilt in the first row facing the sea. The view is incredible, starting with the morning sunrise. It accommodates up to 6 people (4 people in beds and 2 on a sofa bed). Space with 4 environments.

Superhost
A modern living space features sleek design elements with a sectional sofa and a light-colored accent chair. Large glass doors frame views of the outdoor landscape, while a round wooden coffee table is positioned in the center, enhancing the open and inviting atmosphere.
Home
5 out of 5 average rating, 3 reviews

Casa Al Mare

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.

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
4.95 out of 5 average rating, 204 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.

Guest favourite
A vibrant red and white striped lighthouse stands near the water's edge, overlooking a calm sea. A small boat, secured on land, faces the horizon. Lush green hills can be seen in the background under a partly cloudy sky.
Home
4.83 out of 5 average rating, 81 reviews

The Lighthouse-Oceanfront Home in Pico Paradise

The Lighthouse is a stones throw to the ocean. Location is #1! You can taste salty air & drift off to sleep to the sound of waves crashing. A true lullaby.. My property is large with one suite used as a rental. Private, quiet & safe. Grocery store/cafes/bakeries/bars/ATMs & restaurants all within walking distance as well as natural pools&walking trails. You will come for the location but stay for the beauty! Welcome&Enjoy!

Top guest favourite
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.
Holiday home
4.96 out of 5 average rating, 162 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
4.8 out of 5 average rating, 99 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 favourite
A rocky coastline meets calm, clear waters, with dark volcanic stones contrasting with the blue hues of the sea. Irregularly shaped rocks are partially submerged, while patches of greenery are visible along the shore, enhancing the natural landscape.
Home
4.91 out of 5 average rating, 173 reviews

House Above the Rock

Casa Acima da Rocha is “an inch and a half” from the rocks of the coast, with a magnificent view over the Pico-São Jorge canal, where you can be lulled by the whispering of the waves of the sea and the song of the seagulls. It is a newly rebuilt house decorated mostly with recyclables, optimizing existing materials and simultaneously providing comfort to those who enjoy it.

Top guest favourite
Two wooden lounge chairs are positioned to face a panoramic view of the coastline and lush mountains in the background. The clear blue sky and fluffy white clouds enhance the serene atmosphere of this outdoor setting.
Home
4.92 out of 5 average rating, 48 reviews

Refúgio do Pico - Exclusive house with sea view

Panoramafenster, Kaminofen, Küche including Spülmaschine, Terrasse, Grill, W-LAN You can enjoy the exclusive comfort 'of your refuge' including fantastic sea view. On the spacious (about 3,500 m) beautifully landscaped property there are four identical cottages. All houses are nestled between numerous exotic trees and thus offer the space for cozy hours for two.

Guest favourite
The house features a distinctive stone façade with green accents. A covered porch is supported by two columns, offering a shaded area. The roof is tiled in a classic red color, and large windows provide natural light and views of the surrounding landscape.
Villa
5 out of 5 average rating, 5 reviews

Adega do Farol - Adegas do Pico

Adega do Farol belongs to Adegas do Pico, a set of 13 stone houses located in Praínha, Pico island, where the guests enjoy the hospitality and the feeling of the traditional Azorean village. This house is located in front of the sea, with a great view to the sea and São Jorge Island. Local grocery shop, restaurant and Tapas&Wine house within walking distance.

Guest favourite
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
5 out of 5 average rating, 14 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 favourite
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
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!

Popular amenities for Prainha holiday rentals

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