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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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Guest favourite
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, 42 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?

Guest favourite
A charming house with a red-tiled roof is nestled amidst lush greenery, surrounded by colorful flowering plants. The clear blue sky and scattered clouds provide a vibrant backdrop, while the natural landscape creates a serene setting for relaxation.
Home in Santo Amaro
4.97 out of 5 average rating, 35 reviews

Cottage Lima Sol

The Lima Sol house is a charming space, located in a quiet area of the parish of Santo Amaro, where you wake up in the middle of nature and at night you hear the song of the "seagulls." The house has the amenities of a relaxed lifestyle. Open space bedroom/living room with double bed and a sofa bed, a bathroom and a kitchen. In a charming corner, you also have access to a barbecue area. In front are the slopes of the northern part of the island. About 200 meters away is the Portinho bathing area.

Top Guest favourite
A spacious living area features large glass windows that offer views of the sea and mountains. A round wooden dining table is surrounded by four white chairs. A comfortable seating arrangement includes a grey sofa and a rocking chair, under a vaulted wooden ceiling.
Home in Prainha
5 out of 5 average rating, 28 reviews

Nemo's Corner

We are a Portuguese family that knows all the islands of the Azores, and completed in August 2018 this retreat, to get away from our busy lives in London. Until the day comes that we can enjoy it full time, we have decided to share the amazing space we have created with others that love the nature, mountain and sea that is always surrounding us. The house is within Prainha, the most beautiful parish of Pico Island, and within close proximity to the beach, restaurants, grocery store and bakery.

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 Ribeira Grande
4.92 out of 5 average rating, 26 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, 92 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 Canto da Areia
5 out of 5 average rating, 9 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 Baixa
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 favourite
Home in Ribeiras
5 out of 5 average rating, 34 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
Home in Santo António
5 out of 5 average rating, 12 reviews

Pico Sereno · Varanda do Mar | Sea View & Balcony

Fully private 2-bedroom house with a balcony and a view of the Atlantic Ocean, located in a quiet area on Pico Island. Ideal for couples or small families looking for comfort, quiet, and a good location. It has comfortable rooms, an equipped kitchen, a private bathroom, Wi-Fi, and free parking. An excellent base for exploring trails, beaches, vineyards, and viewpoints, always returning to a quiet place to rest.

Guest favourite
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 in Ribeira Seca
5 out of 5 average rating, 5 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 favourite
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 in Ribeiras
5 out of 5 average rating, 27 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 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, 25 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