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Holiday rentals 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
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 favourite
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 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
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.

Top 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
4.98 out of 5 average rating, 42 reviews

Cottage Lima Sol

A casa Lima Sol é um espaço encantador, situada numa zona calma da freguesia de Santo Amaro, onde acorda no meio da natureza e à noite tem o canto dos "cagarros". A casa tem as amenidades de um estilo de vida descontraído. Open space quarto/sala com cama de casal e um sofá cama. uma casa de banho e uma cozinha. Num recanto encantador também tem acesso a uma zona com churrasqueira. Á frente surgem as encostas da zona norte da ilha. A cerca de 200 mt encontra a zona balnear do Portinho.

Guest favourite
Home
5 out of 5 average rating, 11 reviews

Casa Al Mare

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.

Top guest favourite
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.

Guest favourite
A cozy corner of a living area features a light grey sofa adorned with a decorative pillow. A small round side table houses decorative accents, while a vintage armchair complements the space. Natural light filters through sheer curtains, enhancing the room’s serene ambiance.
Flat
5 out of 5 average rating, 5 reviews

"Hommage" Suite 6

This special place is close to everything, making it easy to plan your visit.Welcome to our beautifully restored historic house in the heart of Horta. This stunning building has been thoughtfully renovated to the highest standards, blending its rich heritage with modern luxury. Each of our unique apartments/suites is a tribute to the building’s past, offering an authentic experience with contemporary comfort.

Superhost
The exterior of a two-story stone house is showcased, featuring large glass windows that provide ample natural light. A green door adds a pop of color against the textured stone wall. The surrounding area is characterized by lush greenery and a clear blue sky.
Home
4.8 out of 5 average rating, 110 reviews

Fish House 3

O paraiso na terra. A vista mais bonita do mundo! Maravilhosa casa construida de raiz recentemente, situada na Prainha de Cima ( zona Norte da ilha do Pico) com vista deslumbrante sobre o canal e sobre a ilha de São Jorge. Composta por 2 pisos com 2 janelas panorâmicas, pode alojar 4 pessoas, 2 no quarto e 2 na sala em sofá-cama. Tem 2 WC's completos. Vale mesmo a pena acordar para ver o nascer do sol!

Top 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
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 favourite
A traditional seaside house is displayed, featuring white walls complemented by blue trim. Two windows flank the entrance, providing views of the immediate surroundings. The serene ocean can be seen in the background under a clear sky, enhancing the tranquil atmosphere of the location.
Home
4.87 out of 5 average rating, 86 reviews

Casa da Matilde, na paradisíaca fajã de São João.

Casa de férias ao estilo tradicional, mas com um toque moderno e colorido. À beira mar, com vista esplêndida para a vizinha ilha do Pico, pode descansar ao som do murmurar das ondas e do canto dos pássaros. Ambiente calmo e familiar. Atenção – o acesso à casa implica escadas exteriores (ver fotos), com cerca de 40 degraus.

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
5 out of 5 average rating, 31 reviews

Casa das Duas Ribeiras

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.

Popular amenities for Cascalheira holiday rentals