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Holiday houses in Rua dos Caldeiroes

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Top-rated holiday rentals in Rua dos Caldeiroes

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious bedroom features a large bed adorned with a patterned throw. Floor-to-ceiling glass doors lead to a private outdoor space, allowing views of the ocean and surrounding greenery. Wooden beams grace the ceiling, creating an airy and open atmosphere.
Villa in S.Roque do Pico
4.94 out of 5 average rating, 18 reviews

Casa da Floresta

Beautiful and spacious stone house, perfect for a holiday with family or friends, with a large balcony and a breath-taking view of the whole island of São Jorge and the canal, as well as, to the left, the beautiful bays and parishes of the northern Pico coastline. You see and hear the Atlantic Ocean waves and the birds. Have your meals in the open spacearea of the fully equipped kitchen and dining / living rooms with glass sliding doors or outside on the balcony watching the sunset - you'll never forget the moment. 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. Come live a dream...

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Guest favourite
A spacious living area features a light-colored sofa and a wooden coffee table crafted from natural materials. At the back, a dining table is set, surrounded by four chairs, with a minimalist kitchen visible in the background. Large windows provide soft natural light.
Villa in Conceição
4.93 out of 5 average rating, 29 reviews

Villa vue sur la mer et accès plage à pied

Relax in this unique and peaceful accommodation. Located in the valley of Almoxarife. 5 min walk to the most beautiful black sand beach of the island and 10 mins to the famous Horta marina and landmark downtown by car. Completely renovated, the house offers all modern comforts. All rooms have sea views. The villa "Quinta dos Maracujas" is a located on a vast orchard, where, depending on the season, you will be able to enjoy the exotic fruits. Bars and restaurants at the bottom of the street.

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Superhost
A covered terrace features woven seating options with plush cushions and a glass-topped table. Lush greenery surrounds the area, while the sunset casts a warm glow in the background. Large windows allow for natural light to fill the space, creating an inviting atmosphere.
Cabin in São Mateus
4.82 out of 5 average rating, 108 reviews

The Wooden House - 5 guests, BBQ

Sea, Nature, Resort offers a 110m2 cosy home,fantastic ocean and mountain views, baby equipment, 40 sqm roofed terrace, Internet, 3 bedrooms (16m2): double + single, 3 single, 2 single beds, 10m2 bathroom + shower + tub, washing machine, tumble dryer, guest toilet, 50m2 living room/kitchen, dish washer, induction cooking, electrical oven, microwave, BBQ, natural swimming pool 400m distance. Hiking along coast/vineyards. Madalena port 20mins; Airport 30mins, S. Roque port 40 mins drive.

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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
4.93 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.

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Guest favourite
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 in Madalena
4.94 out of 5 average rating, 103 reviews

Adega da Quinta- Casa do Camolas

Relaxe neste cottage com um spot único e tranquilo. Aprecie na piscina, jacuzzi ou sauna a vista fantástica sobre o Faial, o mar e a vila da Madalena. Desfrute de uma linda casa em madeira num lugar único e especial com piscina, jacuzzi e sauna. Beneficie dos passeios pedestres com vista para a maravilhosa montanha do Pico. As nossas acomodações situam-se a 2 minutos de carro e 20 minutos a pé da Vila da Madalena, incluem um quarto com cama de casal e uma sala que dispõe de sofá cama.

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Guest favourite
Home in Canto da Areia
5.0 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.

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Top Guest favourite
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, 222 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.

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Guest favourite
Cabin in São Roque do Pico
5.0 out of 5 average rating, 7 reviews

Casa da Camélia

Casa de campo, charmosa com vista para a Vila de São Roque do Pico, Canal entre Pico e São Jorge e a vizinha ilha de São Jorge. Esta casa é um refúgio de tranquilidade, simplicidade. Desfrute de dias tranquilos nesta encantadora casa de campo, rodeada pela natureza. Ideal para quem procura descanso, silêncio e paisagens bonitas. A casa oferece um ambiente acolhedor com decoração simples, espaço exterior amplo e áreas perfeitas para relaxar ao ar livre.

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Superhost
Home in São Roque do Pico
5.0 out of 5 average rating, 4 reviews

Pico Sereno - Casa Montanha | Vista Montanha

Casa Montanha é um refúgio acolhedor e reservado na Ilha do Pico, ideal para quem procura tranquilidade e contacto com a natureza. Com uma vista privilegiada para a Montanha do Pico, combina conforto, privacidade e charme açoriano. Rodeada por vegetação, oferece um ambiente sereno para relaxar após um dia de trilhos, observação de baleias ou descoberta da ilha. O local perfeito para desacelerar, respirar fundo e criar memórias inesquecíveis.

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Superhost
An aerial view captures a serene landscape characterized by terraced vineyards and black stone walls, with a distant view of the Pico mountain under a dynamic sky. The layout includes several houses along winding roads, integrating the natural beauty of the area.
Tiny home in Lajido
5.0 out of 5 average rating, 4 reviews

Paraíso do Triângulo II

Paisagem e natureza são as palavras chave. Inserida numa vinha em plena paisagem protegida da cultura de vinha, classificada como Patrimônio Mundial pela UNESCO o meio envolvente é de cortar a respiração. Rodeada por paredes de pedra, os famosos "currais de vinha", para qualquer lado que olhe irá deparar-se com uma vista fantástica, podendo ver a montanha do Pico, a Ilha do Faial e a ilha de São Jorge (ilhas do Triângulo) e o mar.

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Guest favourite
Villa in Madalena
4.94 out of 5 average rating, 17 reviews

Casa Baleia Laranja Ocean-Front

Experience up close the sea pounding against the volcanic rock of Pico Island. Located on the north coast amidst the UNESCO World Heritage Site, this sea-level, ocean-front property is located 5 minutes by car from Madalena, the largest town and center for shopping on Pico Island. The house, with plenty of parking. sits on a landscaped 5500 square meter (approximately 1.3 acres) property, that also supports a small vineyard.

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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
5.0 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.

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Popular amenities for Rua dos Caldeiroes holiday rentals