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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 in São Roque do Pico
5 out of 5 average rating, 41 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 favorite
Villa in São Roque, Ilha do Pico,
4.91 out of 5 average rating, 35 reviews

Casa do Alecrim

Beautiful and spacious house, ideal for holidays with family or friends. The breath-taking view allows you to see the entire island of São Jorge and the canal, as well as bays and parishes on the beautiful and jagged north coast of Pico, with its undulating sea waves. The song of birds and the Atlantic waves are heard. Dine indoors or on the balcony watching the sunset, relax in the lounge chairs with a wonderful drink. The living room has glass sliding doors which invite outdoors in. Come see what you have been missing - you won’t want to leave.

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 in Santo Amaro
4.99 out of 5 average rating, 85 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 in Ribeira Grande
4.92 out of 5 average rating, 25 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, 91 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.

Top guest favorite
Cabin in Santana
5 out of 5 average rating, 19 reviews

Casinha Melissa

What you can expect at Casinha Melissa: • queen-size bed with memory foam mattress • USB/USB-C ports built-in to the light socket at each bedside table • 43" Smart TV for streaming on all major apps or watching cable • WIFI connection with high-speed internet • ceiling fan • air-conditioning/heating system • private on-site laundry with steam dryer option or clothesline located behind the house (clothes pins provided) • personal picnic table • firewood for the fire pit

Guest favorite
Home in Ilha do Pico
5 out of 5 average rating, 31 reviews

Terraced Houses 1

Relax in this paradise surrounded by nature and sea. Casa dos Socalcos is a charming space, located in Terra Alta, parish of Santo Amaro, where you will wake up in the middle of nature and with an extraordinary view of the Pico / São Jorge channel. The house has the amenities of a relaxed lifestyle. It has a bedroom / living room with 2 twin beds, a bathroom and a kitchen. The pedestrian trail "Caminho das voltas" passes right in front of the house.

Superhost
Home in Calheta de Nesquim
4.86 out of 5 average rating, 65 reviews

Nesquim's little house - Pico, Azores

Casinha de Nesquim is a small house from 1883 that has been recently renovated. Surrounded by the lush nature of the Azores and the sea, it is the ideal vacation spot for those looking for the best 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 at home. The outdoor space, with different environments and views, will offer you unforgettable moments.

Superhost
Home in Piedade
4.76 out of 5 average rating, 21 reviews

Quinta do Basalto- Casa Cacto

An old farmhouse transformed into an elegant accommodation where many contemporary elements are punctuated. These are cottages loaded with history. Quinta do Basalto offers an intimate, calm, private atmosphere for guests to enjoy a breathtaking view with a lush and unique landscape. Quinta do Basalto is the ideal frame for a fantastic landscape on Pico Island that will make your vacation unforgettable!

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 in Ribeiras
5 out of 5 average rating, 26 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.

Top guest favorite
A private outdoor pool reflects the sky, surrounded by a well-maintained area with lush greenery. In the background, the scenic view of the island of Faial is visible, with rocky formations and the ocean extending towards the horizon.
Home in Madalena
5 out of 5 average rating, 23 reviews

Villa Valverde

Relax with the whole family at this peaceful place to stay. Completed in 2024, Villa Valverde is located near the center of Madalena, overlooking the island of Faial. Set in a quiet environment, with a large lawn, a private outdoor pool and a barbecue area, it is the ideal place for family vacations.

Guest favorite
A rustic basalt house is positioned near the coastline, showcasing a vibrant red door and surrounding greenery. The tranquil sea is visible in the background, while the structure is accompanied by a well-maintained pathway leading to the entrance.
Home in Lajes do Pico
4.86 out of 5 average rating, 29 reviews

Adega Velha AL house by the sea

Adega Velha is a friendly rustic little house made of basalt. You have all comfort for a dream vacation. It is very close to the sea and a natural pool in a vineyard area. The atmosphere is calm inviting you to a relaxing vacation

Popular amenities for Cascalheira vacation rentals

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