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Holiday rentals with a pool in Ilha de São Jorge

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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
An infinity pool stretches across the foreground, reflecting the sky and surrounding greenery. In the background, two rustic cabins are nestled among lush vegetation, with a scenic ocean view and rolling hills under a partly cloudy sky.
Villa in São Roque do Pico
5 out of 5 average rating, 5 reviews

Casa do Curral

Beautiful lava house in an area where there were stone animal pens which gave it its name. It offers breath-taking views: the entire island of São Jorge and the canal, in front, and, on the left, undulating bays of parishes on the beautiful north coast of Pico. Birds and sea waves are heard. You can dine inside in a modern rustic open spacestyle living / dining room, or outdoors, while enjoying the view of an absolutely sublime sunset and a completely starred sky. 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. Amazing...

Guest favourite
Cottage in Foros
5 out of 5 average rating, 5 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!

Top 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
4.95 out of 5 average rating, 96 reviews

Adega da Quinta - Casa do Camolas

Relax in this cottage with a unique and tranquil spot. Enjoy the fantastic view of Faial, the sea and the village of Madalena in the pool, Jacuzzi or sauna. Enjoy a beautiful wooden house in a unique and special place with a swimming pool, Jacuzzi and sauna. Benefit from the walking tours overlooking the wonderful Pico mountain. Our accommodations are located a 2-minute drive and a 20-minute walk from Vila da Madalena, and include a bedroom with a double bed and a living room with a sofa bed.

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.

Superhost
A stone pathway leads into a welcoming entrance, flanked by white wooden gates. The signage displays the name 'As Casas da Vinha', accompanied by lush greenery and a clear blue sky overhead. Neatly arranged rocks provide a functional and attractive surface for visitors.
Villa in Criacao Velha
4.88 out of 5 average rating, 8 reviews

The Wine Houses - Casa Uva

Inserted in the Protected Landscape of the Vineyard Culture, a UNESCO World Heritage Site, Casas da Vinha is a place of excellence to relax and enjoy your stay in Pico. Just 3 km from the center of Madalena, we have 3 one-bedroom apartments, a two-bedroom apartment and a studio apartment, all fully equipped, with a small outdoor terrace and access to the common outdoor area, with a swimming pool, solarium, dining area and barbecue, as well as a swing for the little ones in the house.

Superhost
Home in São Roque do Pico
4.88 out of 5 average rating, 8 reviews

Casa da Faia

A Hidden Paradise in Nature Escape to this unique stone retreat, where modern design meets breathtaking natural beauty. Perched between lush greenery and stunning views of the ocean and mountains, it’s the perfect place to unwind and reconnect. Experience tranquility, privacy, and elegance all in one unforgettable stay. Book now and make this hidden paradise yours.

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.
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!

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.

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

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.

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
4.57 out of 5 average rating, 23 reviews

2-bedroom apartment - Pico Dreams, Sportfish, Pico

“Pico Dreams-Sportfish” São Roque do Pico, Pico Island, Azores. Apartment with 2 bedrooms, both with double beds, living room with kitchenette, bathroom. Shared pool and barbecue. Sea view, São Jorge Island and Pico Mountain. Close to restaurant, grocery store and natural pools.

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 (Lower Beach)

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.

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