Vacation 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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Guest favorite

A view of the stone cottage surrounded by a landscaped garden featuring various plants and flowers. The cottage displays a wooden deck with lounge chairs, enhancing the connection to the outdoor space. Other structures are visible in the background, situated among the greenery.

Villa in São Roque do Pico

5 out of 5 average rating, 34 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?

A rugged stone opening frames a serene view of the Atlantic Ocean, bordered by lush greenery. The sky reflects soft blue hues, while distant trees and rolling hills hint at the natural beauty surrounding the area.

Farm stay in São Roque do Pico

4.86 out of 5 average rating, 7 reviews

Waka_Land_Azores

Experience the quiet, peaceful island of Pico, enjoying activities on land and ocean, while staying at our cosy and beautiful 2 houses, with incredible views, in recovered ruins, with great comfort and all commodities, in a 10.000 sqm plot. Fire pits, Hammocks, Pool/tank. Star gazing. Facing Atantic Ocean, São Jorge or Faial Islands, Pico Mountain surrounded by vivid blues and greens, within a short drive of the sea, world-class hiking, diving, snorkelling, birdwatching, whale watching

Guest favorite

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

4.96 out of 5 average rating, 56 reviews

Quinta-Casa da Pipas Wine Cellar

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

Top guest favorite

A neatly arranged pathway leads through a white wooden gate, showcasing a stone walkway framed by green grass. The entrance features a sign displaying 'As Casas da Vinha,' complemented by a backdrop of rustic buildings under a blue sky with scattered clouds.

Villa in Criacao Velha

5 out of 5 average rating, 10 reviews

The Wine Houses - Casa Parreira

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 favorite

An expansive outdoor space features a sleek swimming pool surrounded by sun loungers. A rustic stone table is positioned nearby, providing an ideal spot for dining. The structure's large windows allow for ample natural light, and the backdrop showcases lush greenery and distant mountains.

Villa in Madalena

5 out of 5 average rating, 19 reviews

PicoTerrace

PicoTerrace, um sítio único! Conforto e design, com vista panorâmica. Situado na Madalena, disponibiliza jardim, comodidades para churrasco e um terraço, com estacionamento privado no local e de acesso Wi-Fi gratuito. A Villa inclui 2 Quartos com cama de casal e possibilidade de instalar sofá cama, uma sala de estar, televisão por cabo, uma cozinha equipada e casa de banho com uma banheira de hidromassagem e chuveiro. Aproveite os momentos!

Superhost

The image showcases a clear blue swimming pool set against a backdrop of green mountains. A white house with yellow accents can be seen nearby, featuring windows framed with green. The bright blue sky above completes the serene outdoor setting.

Home in Açores

4.42 out of 5 average rating, 24 reviews

Quinta do Girassol - Alagoas

Welcome to Quinta do Girassol! In this space you can find a villa with 2 bedrooms, a bathroom and kitchen. Outside, a swimming pool with half bathroom and also a barbecue area with half bedroom. Please leave the space as you found it and pay special attention to the pool area, always trying to preserve the quality of the water. We wish you a pleasant stay and if you have any questions or concerns do not hesitate to contact us!

Superhost

A modern stone retreat is elevated on a hillside, surrounded by lush green foliage. Large glass windows allow natural light to flood the interior, while wooden accents enhance the design. Two minimalist chairs are placed on the balcony, offering a serene view of the landscape.

Home in São Roque do Pico

4.83 out of 5 average rating, 6 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.

Top guest favorite

The outdoor space includes a stone-paved area surrounding a swimming pool, complemented by lounge chairs. Nearby, a rustic stone house with a red roof is visible, along with a cylindrical wooden sauna. Lush greenery and hills provide a serene backdrop.

Apartment in Calheta

4.91 out of 5 average rating, 23 reviews

Kuanza Nature Experience - Bela Lua

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 favorite

An outdoor pool area features three wooden lounge chairs positioned on a stone patio, facing a scenic view of hills and sunset. Lush greenery surrounds the space, while a distant island silhouette adds to the tranquil atmosphere.

Home in Madalena

5 out of 5 average rating, 16 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.

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

4.55 out of 5 average rating, 22 reviews

2 bedroom apartment - Pico Dreams, Sportfish, Pico

“ Pico Dreams-Sportfish”São Roque do Pico, Ilha do Pico, Azores. Apartment with 2 bedrooms , both with double bed, living room with kitchenette, bathroom. Common pool and barbecue. Sea view, São Jorge Island and Pico mountain. Near the restaurant, grocery store and swimming pools.

Top guest favorite

An outdoor pool with a clear blue surface reflects the sky, surrounded by lush greenery. Lounge chairs are positioned beside the pool, inviting relaxation. In the background, the ocean waves can be seen gently breaking against the shore under a partly cloudy sky.

Cottage in Santo Amaro - S. Roque do Pico

4.95 out of 5 average rating, 110 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!