Holiday rentals with a pool in São Jorge

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Top-rated rentals with a pool in São Jorge

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Guest favourite

Home in São Roque, Ilha do Pico

4.95 out of 5 average rating, 21 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

Villa in S.Roque do Pico

5 out of 5 average rating, 33 reviews

House of 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?

Guest favourite

Cabin in Madalena

4.98 out of 5 average rating, 44 reviews

Adega da Quinta-Casa da Pipas

Relax to the sound of nature, in this calm and elegant space, enjoying a swimming pool, Jacuzzi and sauna on a farm with a paradisiacal view over Vila da Madalena, the sea and Faial Island and benefit from pedestrian walks with a view of Pico mountain. Our accommodations are located 2 minutes by car and 20 minutes walk from Vila da Madalena, include a bedroom with a double bed and a living room with a sofa bed. You can enjoy a sauna and a fire guess.

Guest favourite

Villa in Criacao Velha

5 out of 5 average rating, 23 reviews

As Casas da Vinha - Casa Canada

Nestled in the Protected Vineyard Culture, a UNESCO World Heritage Site, Casas da Vinha is a place of excellence for relaxing and enjoying your stay at Pico. Just 3 km from the center of Madalena, we have 3 apartments T1, a T2 apartment and a T0 apartment fully equipped, with a small outdoor terrace and access to the common outdoor area, with swimming pool, solarium, dining and barbecue area, as well as a swing for the little ones in the house.

Guest favourite

Home in candelaria

5 out of 5 average rating, 11 reviews

Happy Bird House!

Sit back and relax in this quiet, stylish space. Nestled in nature on a traditional Adega estate combined with all its amenities such as swimming pool, sauna, fantastic garden, several sun decks, sea views and PicoBlick as well as its own large wooded area, here you will find a newly renovated guest house on 55 sqm with kitchen, bathtub and enough space to relax.

Superhost

Serviced apartment in Calheta

4.92 out of 5 average rating, 12 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!

Guest favourite

Home in Madalena

5 out of 5 average rating, 9 reviews

Villa Valverde

Relax with the whole family in this quiet accommodation. Completed in 2024, Villa Valverde is located near downtown Madalena, in a place overlooking the island of Faial. Set in a quiet surroundings, with a large lawn, a private outdoor pool and a barbecue space, it is the ideal place for a family vacation.

Superhost

Rental unit in São Roque do Pico, Ilha do Pico

4.67 out of 5 average rating, 21 reviews

T3-Pico Dreams House - Sportfish, Pico Island

Pico Dreams-Sportfish. São Roque do Pico, Ilha do Pico, Azores. Apartment with 3 bedrooms, 3 double beds and 1 single, living room, kitchen, bathroom and terrace. Pool and barbecue in common. Sea view, São Jorge Island and Pico mountain. Nearby restaurants, grocery store and natural pools.

Guest favourite

Cottage in Santo Amaro - S. Roque do Pico

4.97 out of 5 average rating, 98 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, your water is 28.º C - Bliss!