Vacation rentals in Cascalheira

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Top-rated vacation rentals in Cascalheira

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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, 35 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?

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

4.75 out of 5 average rating, 85 reviews

Oceanfront Cottage on Pico Island - (RRAL78)

Escape to a peaceful retreat on Pico Island, Azores. Adega da Figueira is a charming oceanfront cottage in the picturesque village of Calheta de Nesquim. Combining the rustic charm of traditional Azorean stone architecture with comfort, this unique home is perfect for couples, families, or solo adventurers seeking tranquility and stunning views. Wake up to panoramic views of the Atlantic Ocean. Enjoy sunsets from the private terrace or explore the nearby natural swimming pools.

Guest favorite

An outdoor seating area is depicted with two chairs and a small table, positioned on a gravel surface. A hanging chair is included, offering a cozy spot. Surrounding greenery adds a natural touch, complemented by stone walls and red doors of nearby structures.

Home in Calheta de Nesquim

4.91 out of 5 average rating, 56 reviews

Nesquim's little house - Pico, Azores

Casinha de Nesquim is a small house from 1883 that was completely refurbished in 2019. Surrounded by the luxuriant 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, fresh air, stunning landscapes 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.

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, 197 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

An outdoor seating area is positioned to take in panoramic views of the Atlantic Ocean. Modern white chairs and a small table are arranged on a stone terrace, surrounded by lush greenery and flowering plants. The tranquil landscape enhances a peaceful atmosphere.

Home in Ribeiras

5 out of 5 average rating, 25 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

A stone apartment is nestled among lush greenery and colorful hydrangeas. A winding pathway leads to the entrance, framed by vibrant foliage and tropical plants, with a clear blue sky overhead enhancing the serene outdoor environment.

Home in Terra Alta

4.9 out of 5 average rating, 20 reviews

Modern Apartment w/ Ocean View

Experience elegance in this one-bedroom, one-bathroom apartment, inspired by Azorean architecture and crafted from native lava rock. Timeless design meets modern luxury, complete with the latest amenities. Nestled in a vibrant garden, a secluded patio offers a serene space to enjoy morning coffee, with the Atlantic's expanse and São Jorge Island's silhouette enhancing the horizon. Follow us @highlandhomes.pico on IG

Top guest favorite

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 in Santo Amaro

4.92 out of 5 average rating, 170 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.

Guest favorite

A traditional stone house features a sloped roof and white-framed windows, surrounded by greenery. An outdoor balcony provides seating, while a stone wall encloses the front yard, enhancing privacy. The backdrop displays rolling hills, typical of the Pico landscape.

Home in Lajes do Pico

4.75 out of 5 average rating, 135 reviews

Casa do Lampião, for vacation on Ilha do Pico

House located in Santa Cruz, parish of Ribeiras (Ilha do Pico), with magnificent ocean views. It can accommodate up to 3 people, 2 bedrooms, an equipped kitchen, a toilet and a TV. Extremely quiet location, with an outside balcony, parking space, a 30-meter walk to an excellent municipal swimming pool, free of charge. Great place for kids and for rest.

Guest favorite

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 in Santo Amaro - S. Roque do Pico

4.95 out of 5 average rating, 112 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!

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 in Lajes do Pico

4.96 out of 5 average rating, 23 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.