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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

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Superhost
The cozy bedroom features two spacious beds adorned with soft linens. A large glass window offers a sweeping view of the vibrant landscape and ocean beyond. Natural light filters in through sheer curtains, creating a serene and inviting atmosphere.
Home in São Roque, Ilha do Pico
4.78 out of 5 average rating, 37 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 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, 38 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 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
4.96 out of 5 average rating, 91 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.

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, 38 reviews

The Wine Houses - Casa Jeirão

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.

Guest favourite
An aerial view captures the coastal landscape with lush green hills meeting the ocean. Waves can be seen crashing on the rocky shore, while a small village is nestled among the greenery, featuring buildings with terracotta roofs.
Serviced apartment in Calheta
4.93 out of 5 average rating, 14 reviews

Kuanza Nature Experience - Bela Vista

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, 20 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
An outdoor area features a clear blue swimming pool surrounded by a grassy lawn. Multiple lounge chairs are placed around the pool. The ocean and distant mountains are visible in the background, with a covered space that includes a barbecue grill.
Flat in São Roque do Pico
4.68 out of 5 average rating, 22 reviews

T3-Pico Dreams - Sportfish, Pico Island

Pico Dreams-Sportfish. São Roque do Pico, Pico Island, Azores. Apartment with 3 bedrooms, 3 double beds and 1 single, living room, kitchen, bathroom and terrace. Shared pool and barbecue. Sea view, São Jorge Island and Pico Mountain. Close to restaurants, grocery store and natural pools.

Top 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
4.95 out of 5 average rating, 116 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!

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, 12 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.

A Jacuzzi is shown with foam bubbles rising, overlooking a stunning ocean view. A glass of white wine is placed beside a book on the edge, reflecting the sunlight. The serene atmosphere is highlighted by the calm waters and clear sky.
Home in Ginjeira
4.81 out of 5 average rating, 27 reviews

Laranja-pool, jacuzzi, BBQ

Villa da Gingeira is located in a quiet place with stunning views of the ocean and mount Pico, for our guests we offer to relax in the Jacuzzi, swim in the pool with sea water, if desired, we organize breakfasts consisting of products of the Azores

Superhost
An infinity pool is framed by wooden decking, overlooking a scenic coastal view. Comfortable lounge chairs are positioned nearby. The clear water reflects the sky, enhancing the serene landscape that includes distant islands and rolling hills.
Home in São Roque do Pico
4.84 out of 5 average rating, 32 reviews

The Ombudsman's House - Casa Fogo

Casa do Ouvidor offers luxuriously furnished houses. They feature panoramic views of the Atlantic Ocean, the large canal between Pico and Island of S. Jorge. The property is composed of 3 houses, each with 2 bedrooms with private bathrooms.

A small swimming pool is visible in the foreground, surrounded by a clean white wall. Two striped lounge chairs are positioned to one side, with a backdrop of lush green hills under a clear blue sky.
Home in São Mateus
4.8 out of 5 average rating, 172 reviews

Valsa House, Pico Island, Azores

Casa da Valsa is located in the parish of São Mateus, 15 km from the village of Madalena. You'll be able to enjoy all the amenities for a relaxing and calm vacation. Make yourselves at home.

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