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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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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
5 out of 5 average rating, 43 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?

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

Guest favorite
An outdoor jacuzzi is positioned beneath a wooden pergola, offering panoramic views of the surrounding landscape, ocean, and distant village. The clear blue sky and scattered clouds create a tranquil atmosphere, enhancing the unique setting for relaxation.
Cabin
4.94 out of 5 average rating, 103 reviews

Adega da Quinta - Casa do Camolas

Relax in this cottage with a unique and tranquil spot. Enjoy the fantastic view of Faial, the sea and the village of Madalena in the pool, Jacuzzi or sauna. Enjoy a beautiful wooden house in a unique and special place with a swimming pool, Jacuzzi and sauna. Benefit from the walking tours overlooking the wonderful Pico mountain. Our accommodations are located a 2-minute drive and a 20-minute walk from Vila da Madalena, and include a bedroom with a double bed and a living room with a sofa bed.

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, 12 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, 37 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 favorite
Home
5 out of 5 average rating, 20 reviews

Pico Sereno · Sea Balcony | Sea View & Balcony

Fully private 2-bedroom house with balcony and sea view of the Atlantic, set in a quiet environment on Pico Island. Ideal for couples or small families looking for comfort, silence and a good location. It has comfortable bedrooms, an equipped kitchen, a private bathroom, Wi-Fi and free parking. Excellent base for exploring trails, beaches, vineyards and viewpoints, always returning to a quiet space to rest.

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, 32 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.

Popular amenities for Cascalheira vacation rentals