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Holiday rentals in Cascalheira

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Top-rated holiday rentals in Cascalheira

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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 Santo Amaro
5 out of 5 average rating, 12 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
A charming guesthouse sits on the edge of a cliff with sweeping views of the Atlantic Ocean. A spacious wooden deck features picnic tables and is surrounded by greenery, while the house's white exterior is complemented by dark shutters and a welcoming entrance.
Home in Horta
5 out of 5 average rating, 4 reviews

Casa da Guia - Two Bedroom House

Casa da Guia is a charming guesthouse located in Horta. It's known for its stunning views of Pico Island and the Atlantic Ocean. This house offers a cozy and welcoming atmosphere, is often recommended for its serene setting, allowing guests to relax and soak in the breathtaking views while being close enough to explore the attractions Faial Island has to offer. Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!

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, 80 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

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 Ribeiras
4.94 out of 5 average rating, 16 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
A sturdy stone structure is observed with a wooden porch, inviting relaxation. Two individuals can be seen sitting on the porch, surrounded by vibrant green foliage and blooming red flowers. A certification label indicating 'Clean & Safe' is visible in the corner.
Cottage in Calheta de Nesquim
4.76 out of 5 average rating, 88 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.

Superhost
Home in Calheta de Nesquim
4.87 out of 5 average rating, 62 reviews

Nesquim's little house - Pico, Azores

Casainha de Nesquim is a small house from 1883 that was completely remodeled in 2019. Involved between the luxurious nature of the Azores and the sea, it is the ideal vacation space for those looking for the best that the island has to offer: tranquility, clean air, stunning scenery and the sea. The fully equipped house offers all the comfort to make you feel like you are in your own home. The outdoor space with different environments and views will offer you unforgettable moments.

Superhost
Home in Prainha
5 out of 5 average rating, 3 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.

Guest favourite
Home in Ribeirinha
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, 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 favourite
Home in Ribeiras
5 out of 5 average rating, 27 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.

Top guest favourite
Two wooden lounge chairs face a stunning view of coastline and mountains, framed by lush greenery. A clear blue sky with scattered clouds enhances the serene atmosphere of the outdoor space.
Home in Prainha
5 out of 5 average rating, 7 reviews

Refuge of Pico - 2

Enjoy the exclusive comfort of your retreat including fantastic ocean views. "Refúgio do Pico – 2" is one of four identical vacation homes located on a spacious 3,500 m² property. The houses are nestled between numerous exotic trees, have a wonderful sea view and are identical in furnishings and fittings. Each vacation home of the Refúgio do Pico has everything you need for a comfortable stay.

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, 22 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.

Popular amenities for Cascalheira holiday rentals

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