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Holiday rentals with a pool in Ilha de São Jorge

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ilha de São Jorge

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Superhost
Home in São Roque, Ilha do Pico
4.79 out of 5 average rating, 38 reviews

Casa da Figueira

House of Figueira, a charismatic and modern house. We adapted the architecture to insert it in a natural and graceful way on the extremely sloping terrain, resulting in a duplex with the two rooms on the lower floor, both with a spectacular view of the sea, the island of São Jorge and a wonderful sunrise. Its sumptuous balcony that includes stone barbecue has an unobstructed and stunning view of the entire island of São Jorge, the beautiful canal and a garden.Upstairs, dazzle yourself again and enjoy a drink in lounge chairs or outdoor dining with unsurpassed views. The interior space, in open space style , is cozy and comfortable. As if that were not enough, there is an additional treat: on the left-hand side of the porch, a sunset like a Hollywood movie, so perfect that it looks like a mirage. All rooms have views and the room with glazing from ceiling to floor on sliding doors open the interior to the exterior reminiscent of heaven on earth. Yeah, it's here.

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 São Roque do Pico
4.94 out of 5 average rating, 16 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...

Guest favourite
Cottage in Foros
5 out of 5 average rating, 6 reviews

Bioma Adega - Gourmet Stay

Next to the BIOMA restaurant, discover a space designed for those seeking more than just a place to stay — an authentic experience in a traditional Azorean Adega. A cozy suite, perfect for two, with a living room facing the ocean, where the view stretches to the horizon. Start your day with a lovingly prepared breakfast. With a private pool, the Atlantic at your feet, and surrounded by the island’s lush green nature. A peaceful retreat designed to rest, inspire, and create lasting memories!

Guest favourite
An outdoor heated infinity pool reflects the bright blue sky and surrounding greenery. The calm water creates a seamless view of the horizon, showcasing the distant landscape of Faial Island against a backdrop of soft clouds.
Home in Criacao Velha
5 out of 5 average rating, 27 reviews

Atlantic Heritage Luxury Villa

The Atlantic Heritage Luxury Villa is located in the beautiful historical village of Criação Velha, on Pico Island, the second largest island in the Azores. This stunning, newly constructed luxury villa has 4 en-suite bedrooms, an Outdoor Heated Infinity pool and an Indoor Jacuzzi. A perfect place for a romantic getaway, a family vacation, creative writing and study, or a relaxing and meditative retreat. Breakfast included with your reservation, Daily cleaning and personal assistant.

Top guest favourite
A white wooden gate opens to a cobblestone pathway leading to neatly arranged buildings. Lush green grass lines the sides of the walkway, complemented by a few trees. A clear blue sky is visible above, enhancing the serene surroundings of the property.
Villa in Criacao Velha
5 out of 5 average rating, 42 reviews

As Casas da Vinha - Casa Jeirão

Inseridas na Paisagem Protegida da Cultura da Vinha, Património da Humanidade da UNESCO, as Casas da Vinha são um local de excelência para relaxar e aproveitar a estadia no Pico. A escassos 3 km do centro da Madalena, dispomos de 3 apartamentos T1, um apartamento T2 e um apartamento T0 completamente equipados, com um pequeno terraço exterior e acesso à zona exterior comum, com piscina, solário, zona de refeições e churrasco, assim como um baloiço para os mais pequenos da casa.

Guest favourite
The image features a wooden structure with large glass doors, adjacent to a rectangular swimming pool. Surrounding trees and a clear blue sky enhance the serene outdoor setting. A jacuzzi and seating area are visible, situated on a stone patio beside the pool.
Cabin in Madalena
4.97 out of 5 average rating, 61 reviews

Adega da Quinta-Casa da Pipas

Relax ao som da natureza, neste espaço calmo e elegante, desfrutando de banho de piscina, jacuzzi e sauna numa quinta com vista paradisíaca sobre a Vila da Madalena, o mar e a Ilha do Faial e beneficie dos passeios pedestres com uma vista para a 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. Pode usufruir de uma sauna e de um firepite.

Superhost
A rustic stone house sits against a backdrop of lush green mountains. The structure features wooden accents and a small balcony. Surrounding vegetation adds to the natural setting, enhancing the connection to the landscape.
Serviced apartment in Calheta
5 out of 5 average rating, 4 reviews

Kuanza Nature Experience - Belo Canto

Kuanza Nature Experience is situated in the unique location of Fajã do Belo. Each of the self-catering houses has a magnificent sea view. The property is a nature lover`s paradise and a surfer`s dream. Relax, unwind and soak up all that Mother Nature has to offer in the company of family and friends. A truly life changing experience!

Top guest favourite
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

Relaxe com toda a família neste alojamento tranquilo. Concluída em 2024, a Villa Valverde situa-se perto do centro da Madalena, num local com vista sobre a ilha do Faial. Inserida num entorno sossegado, com um amplo relvado, uma piscina exterior privada e um espaço de churrasco, constitui o local ideal para férias em família.

Guest favourite
An expansive property features multiple wooden structures with terracotta roofs, surrounded by lush greenery. An outdoor area includes a pool, providing a serene view of a distant mountain under a cloudy sky, enhancing the tranquil landscape.
Villa in Madalena
4.92 out of 5 average rating, 13 reviews

Alma do Pico - T0 House

"Alma do Pico" is a tourist village, known as a nature resort. It is a tranquil village, integrated into nature, with units scattered throughout the property, connected by gardens and paths. Relaxing atmosphere, ideal for couples, families and travelers seeking peace and quiet. Stunning views of the mountain and Faial Island.

Superhost
A private pool area is featured, surrounded by lounge chairs arranged neatly on the tiled patio. A shaded area with a bar is visible in the background, while the ocean and lush greenery are seen beyond the white walls.
Home in São Roque do Pico
4.58 out of 5 average rating, 24 reviews

Apartamento 2 quartos- Pico Dreams, Sportfish,Pico

“ Pico Dreams-Sportfish"São Roque do Pico, Ilha do Pico, Açores. Apartamento com 2 quartos , ambos com cama casal, sala com kitchenette, casa de banho. Piscina e churrasco comuns. Vista mar, ilha de São Jorge e montanha do Pico. Perto restaurante, mercearia e piscinas naturais.

Guest favourite
An aerial view showcases a stone house surrounded by lush greenery and terraced gardens. A private heated pool is centrally located within a well-maintained lawn, complemented by outdoor seating and parking space along a circular driveway.
Cottage in Santo Amaro - S. Roque do Pico
4.94 out of 5 average rating, 119 reviews

Casa do Caisinho Pico - Heated pool near sea

Stay in a dream lava home with a heated outdoor pool and an incredible sea view. Close to the sea, this lava house was fully restored from the ruins of a hundred-year-old lava house. We just installed the pool heating system so that, even in Winter, you can have a swim - Bliss!

Top guest favourite
A dining table is set for breakfast, showcasing plates with yellow napkins and glasses of juice. The pool and ocean views are clearly visible in the background, while green hills frame the serene landscape. Sunlight brightens the scene, enhancing the inviting space.
Home in Prainha
5 out of 5 average rating, 15 reviews

Vacation House Prainha de Baixo

This beautiful house is located at Prainha de Baixo, S. Roque do Pico. The rooms are bright and have modern furnishings. The kitchen is fully equipped, perfect for your family holidays. Very quiet location close to the sea and surrounded by gardens.

Popular amenities for Ilha de São Jorge rentals with a pool