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Holiday houses in Cascalheira

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Top-rated holiday rentals in Cascalheira

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

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Top Guest favourite
The exterior of the stone house is showcased, featuring large glass windows that invite natural light. Surrounding flora includes colorful flower beds, while the backdrop of rolling hills and misty mountains enhances the serene environment.
Villa in São Roque do Pico
5 out of 5 average rating, 14 reviews

Casa do Ilhéu

Dream house, in stone, like all, and with modern design, with a rustic touch. It offers two bedrooms and a complete bathroom on the ground floor. On the upper floor, be dazzled and enjoy the beautiful and large balcony where you can relax on the loungechairs or dine al fresco, with an amazing view of the canal and the whole island of São Jorge. It should be noted that, taking into account that the two floors are connected by an interior staircase, it is not advisable for families with young children. It also has a totally unobstructed view of the bays and parishes of the beautiful and indented north coast of Pico on your left.The interior space, in open spacestyle ,is modern and relaxed sophisticated, with a fully equipped kitchen, living and dining room. As if that were not enough, there is an additional treat: on the left side you will experience a sunset of those surreal and sublime - perfect and unforgettable. All rooms with a view and the living room with ceiling-to-floor glass sliding doors that open the interior to the exterior. Bearing in mind that Casa do Ilhéu is on a slope, it is not recommended for people with motor difficulties and small children. This house is part of a small family resort, within which is available the Magma restaurant, a grocery store, a yoga room and a heated swimming pool. Come live this dream ...

Superhost
Home in São Roque, Ilha do Pico
4.78 out of 5 average rating, 37 reviews

Casa da Figueira

House of Figueira, a charismatic and modern house. We adapted the architecture to insert it in a natural and graceful way on the extremely sloping terrain, resulting in a duplex with the two rooms on the lower floor, both with a spectacular view of the sea, the island of São Jorge and a wonderful sunrise. Its sumptuous balcony that includes stone barbecue has an unobstructed and stunning view of the entire island of São Jorge, the beautiful canal and a garden.Upstairs, dazzle yourself again and enjoy a drink in lounge chairs or outdoor dining with unsurpassed views. The interior space, in open space style , is cozy and comfortable. As if that were not enough, there is an additional treat: on the left-hand side of the porch, a sunset like a Hollywood movie, so perfect that it looks like a mirage. All rooms have views and the room with glazing from ceiling to floor on sliding doors open the interior to the exterior reminiscent of heaven on earth. Yeah, it's here.

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, 82 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

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
4.91 out of 5 average rating, 22 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.

Superhost
Cottage in Calheta de Nesquim
4.77 out of 5 average rating, 90 reviews

Adega da Figueira · Whalers' Ruin & Ocean Views

Nesquim is where the first whaling company in the Azores was born. This stone house was a ruin when we found it — covered by an enormous fig tree that gave it its name. Rebuilt by a local family from the village, with stone from the island and a roof with a story. From the terrace, dolphins pass weekly between May and October. Whales appear between May and August. No boat needed. Just you, the open sea, and a house that was made to feel like home. Guests who come once tend to come back.

Guest favourite
Home in Baixa
5 out of 5 average rating, 7 reviews

Inn Fraga, Pico Island, Azores

Discover Inn Fraga, a charming retreat on stunning Pico Island. Imagine yourself relaxing in a cozy home, where comfort meets tranquility. Wake up to panoramic views of the sea and the iconic island of São Jorge while enjoying a coffee on the balcony. Explore the island's natural wonders, from scenic trails to lush vineyards and beautiful natural pools. At Inn Fraga, every stay is an unforgettable experience of peace and beauty. Come and experience the magic of Pico!

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
4.95 out of 5 average rating, 211 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 favourite
The image features a wooden structure with large glass doors, adjacent to a rectangular swimming pool. Surrounding trees and a clear blue sky enhance the serene outdoor setting. A jacuzzi and seating area are visible, situated on a stone patio beside the pool.
Cabin in Madalena
4.97 out of 5 average rating, 60 reviews

Quinta-Casa da Pipas Winery

Relax to the sound of nature in this calm and elegant space, enjoying a pool, Jacuzzi and sauna on a farm with a paradisiacal view of Vila da Madalena, the sea and Faial Island, and benefit from the pedestrian walks with a view of the Pico mountain. Our accommodations are located 2 minutes by car and 20 minutes on foot from Vila da Madalena, and include a bedroom with a double bed and a living room with a sofa bed. You can enjoy a sauna and a fire pit.

Top Guest favourite
Home in Ribeiras
5 out of 5 average rating, 32 reviews

Views, peace, and quiet

180 degrees of breathtaking views of the Atlantic (at about 200 meters above sea level), a lot of green everywhere and no neighbors in sight: if you're looking for a relaxing vacation in a traditional Azorean stone cottage placed in a magical landscape, this is the place for you. Casas do Horizonte is a traditional compound of two homes (the main farm house and a converted millhouse) set in 2 acres of gardens and wooded areas.

Guest favourite
An outdoor terrace features a shaded area with a large umbrella over a wooden table and four chairs. Potted plants are arranged near the edge, offering a pleasant view of the surrounding greenery. The Clean & Safe certification logo is displayed prominently.
Home in Calheta de Nesquim
5 out of 5 average rating, 24 reviews

Casa da Figueirinha

Located in the countryside and 1 km from the ocean, Casa da Figueirinha is a house of traditional architecture, restored and decorated in a modern and welcoming style so that the visitors have the necessary comfort for a quiet and relaxing holiday in full contact with nature.

Guest favourite
A two-story house is situated on elevated land, featuring a red railing along the spacious terrace. Lush green plants are planted in front of a stone wall, enhancing the natural landscape. The building presents a simple architectural style with a sloped roof under a cloudy sky.
Home in Calheta de Nesquim
4.96 out of 5 average rating, 25 reviews

Ninho da Cagarra Wine Cellar

Casa Ninho da Cagarra is located in the parish of Calheta de Nesquim. It is 150 meters from a bathing area and a picnic park, has a privileged view of the sea, a calm, quiet and paradisiacal place, also has a barbecue and outdoor furniture for greater comfort and convenience.

Top Guest favourite
The image displays a rugged coastline featuring dark volcanic rocks partially covered in green algae near the water's edge. The sea reflects soft hues of blue and orange from the sunset sky. A cottage is visible in the background, set against the hillside.
Cottage in Prainha - São Roque do Pico
4.97 out of 5 average rating, 133 reviews

Oceanfront Cottage: The Boathouse

Originally an early 20th century boathouse, now a cozy oceanfront cottage. It is located in the village of Prainha de Baixo, a small village on the island of Pico.

Popular amenities for Cascalheira holiday rentals

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