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Vacation rentals in Cascalheira

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Top-rated vacation rentals in Cascalheira

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

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Top guest favorite
A spacious bedroom features a large bed adorned with a patterned throw. Floor-to-ceiling glass doors lead to a private outdoor space, allowing views of the ocean and surrounding greenery. Wooden beams grace the ceiling, creating an airy and open atmosphere.
Villa
4.94 out of 5 average rating, 18 reviews

Forest House

Beautiful and spacious stone house, perfect for a holiday with family or friends, with a large balcony and a breath-taking view of the whole island of São Jorge and the canal, as well as, to the left, the beautiful bays and parishes of the northern Pico coastline. You see and hear the Atlantic Ocean waves and the birds. Have your meals in the open spacearea of the fully equipped kitchen and dining / living rooms with glass sliding doors or outside on the balcony watching the sunset - you'll never forget the moment. 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. Come live a dream...

Top guest favorite
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
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

Top guest favorite
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
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.

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
4.75 out of 5 average rating, 96 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 favorite
Home
5 out of 5 average rating, 11 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 favorite
Home
5 out of 5 average rating, 8 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 favorite
Home
5 out of 5 average rating, 36 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.

Superhost
An aerial view captures a serene landscape characterized by terraced vineyards and black stone walls, with a distant view of the Pico mountain under a dynamic sky. The layout includes several houses along winding roads, integrating the natural beauty of the area.
Tiny home
5 out of 5 average rating, 4 reviews

Paraiso do Triângulo II

Landscape and nature are the keywords. Set in a vineyard in the middle of a protected landscape of vineyard culture, classified as a World Heritage Site by UNESCO, the surrounding environment is breathtaking. Surrounded by stone walls, the famous "vineyard corrals", wherever you look you will come across a fantastic view, being able to see Pico Mountain, Faial Island and São Jorge Island (Triangle Islands) and the sea.

Guest favorite
An outdoor terrace is presented with a railing, showcasing expansive ocean views. Two gray lounge chairs are positioned on the concrete surface, surrounded by greenery and open sky. The scene reflects natural light and serenity, inviting moments of relaxation.
Home
5 out of 5 average rating, 9 reviews

Picolo-Mondo - Sunny Suite 16

Picolo-Mondo ,Sunny Suite 16, Pico Island Sunny Suite 16, a radiant Pico Island retreat, shines with golden sunlight and ocean views. Ideal for stargazing, birdwatching, and whale watching. Its large patio with shaded umbrella is perfect for sunset dining. Includes an open kitchen, luxurious bathroom with starlight shower, two queen beds,. Enjoy a welcome basket with Azores coffee, tea, and Pico wine.

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
5 out of 5 average rating, 31 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.

Guest favorite
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
5 out of 5 average rating, 26 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 favorite
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
4.96 out of 5 average rating, 27 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.

Popular amenities for Cascalheira vacation rentals