Vacation 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 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, 33 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?

Guest favorite

A spacious living area features a wooden ceiling and large glass doors opening to a panoramic view of the sea. A round dining table sits centrally, accompanied by a cozy seating area with a sofa and stylish chairs, enhancing the connection to the outdoors.

Villa in São Roque, Ilha do Pico,

4.91 out of 5 average rating, 22 reviews

Casa do Alecrim

Beautiful and spacious house, ideal for holidays with family or friends. The breath-taking view allows you to see the entire island of São Jorge and the canal, as well as bays and parishes on the beautiful and jagged north coast of Pico, with its undulating sea waves. The song of birds and the Atlantic waves are heard. Dine indoors or on the balcony watching the sunset, relax in the lounge chairs with a wonderful drink. The living room has glass sliding doors which invite outdoors in. Come see what you have been missing - you won’t want to leave.

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

5 out of 5 average rating, 4 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 outdoor heated infinity pool is illuminated, reflecting the evening sky. Sun loungers are positioned beside the pool, offering a relaxed seating area. The villa's modern design is complemented by large glass doors that provide views into the living space, enhancing the seamless connection with the outdoors.

Home in Criacao Velha

5 out of 5 average rating, 24 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.

Guest favorite

A wooden cottage is positioned beside a pool, featuring large glass windows that offer views of the surrounding greenery. A hot tub is situated on a stone patio adjacent to the pool, surrounded by lush vegetation and clear skies.

Home in Madalena

4.89 out of 5 average rating, 38 reviews

Quinta-Casa da ioio Wine Cellar

Relax in this cottage with a unique and peaceful 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 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 favorite

A rectangular swimming pool is surrounded by a wooden deck and lounge chairs. A scenic view features the peak of a mountain in the background, while a white trellis structure provides shaded areas nearby. The clear blue sky enhances the inviting atmosphere.

Villa in Criacao Velha

5 out of 5 average rating, 24 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 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, 17 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!

Top guest favorite

An aerial view showcases the property surrounded by lush greenery. A glistening pool is seen adjacent to the guesthouse, along with a covered gazebo and outdoor seating area, providing a tranquil retreat within a natural landscape.

Home in candelaria

5 out of 5 average rating, 16 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.

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, 22 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, 10 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

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.

Apartment in São Roque do Pico

4.67 out of 5 average rating, 21 reviews

Casa T3-Pico Dreams - 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 favorite

A heated outdoor pool is framed by natural greenery and wooden decking, with a scenic view of the surrounding mountains. Sunlight streams onto the water’s surface, while a lounge chair nearby invites relaxation. A distant stone structure adds rustic charm to the serene landscape.

Cottage in Santo Amaro - S. Roque do Pico

4.94 out of 5 average rating, 105 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!

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Popular amenities for São Jorge rentals with a pool

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Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene swimming pool is positioned on a terrace, reflecting clear blue waters under a cloudy sky. Several lounge chairs are arranged nearby, with a rainbow visible over the horizon, enhancing the panoramic ocean view surrounded by lush greenery.

Home in Prainha

5 out of 5 average rating, 6 reviews

Vacation House Prainha de Baixo (Lower Beach)

AlizRating, 5 stars10 months ago

Even before we arrived, we had the feeling that we were warmly welcomed. We received all the necessary information in advance. The house is on a quiet street. The view, the pool and the evening atmosphere are indescribable! At around 10 p.m. the Cory's Shearwaters come back from hunting and hold their "concert" for about 30 minutes. A unique experience that is rare outside of the Azores. The house is very well equipped, you can cook really well and there are also great restaurants not far away. It was super clean. We were given a very warm welcome and everything was explained and shown to us thoroughly. We had a wonderful time in this beautiful house!

An outdoor municipal swimming pool is visible under a clear blue sky. The pool area features a spacious deck with light-colored paving and benches. Several individuals enjoy the water, while buildings and green hills provide a scenic backdrop.

Home in Santa Cruz

4.25 out of 5 average rating, 4 reviews

Pico Boutique House

KeganRating, 5 stars7 months ago

Great location for this part of the island, the home was in great shape, hits way above the price point.

A tranquil infinity pool reflects the colorful hues of the sunset, with serene waters blending into the ocean horizon. Silhouetted trees frame the scene, enhancing the sense of peace in the natural surroundings.

Home in Madalena

5 out of 5 average rating, 3 reviews

Ocean View Pico

CindyRating, 5 stars1 month ago

HANDS DOWN our group of fours' FAVORITE place we have EVER stayed with the most gracious host we have ever encountered. The doors were not only functional, they allowed every part of the house to connect with the outdoors and the ocean. We had several nights in cooking in the kitchen (which had everything needed) because we had a better view than the amazing restaurants that Nicolau had PERSONALLY showed us in a quick town tour after checking us in. He also connected with the restaurant owners to advise who was open and the fresh catch of the day. We all slept so soundly to the sound of the ocean. I felt like I already knew Nicolau the moment he met us as he had provided so much information even before we arrived in Pico. We literally are planning the next time we can return and we cannot do Pico without Nicolau and this special place.

Guest favorite

The exterior showcases a modern stone house amidst lush greenery on a sloped terrain. A rectangular pool is framed by wooden lounge chairs. Pathways meander through garden beds, leading to an inviting entrance with natural stone features.

Home in São Roque, Ilha do Pico

4.92 out of 5 average rating, 26 reviews

Casa da Figueira

PaulaRating, 5 stars1 month ago

Cleide was very sweet and welcoming. The house was very cool. The heated pool is very nice. We enjoyed our stay.

A bright and airy living space is presented, featuring a comfortable green sofa positioned beside a vintage-style lamp. A large mirror is framed elegantly on the wall, reflecting light into the room. Rich wooden flooring adds warmth to the inviting atmosphere.

Home in Calheta de Nesquim

4.5 out of 5 average rating, 4 reviews

T1 Casa das Pereiras (Pereiras' House)

| T IRating, 5 stars9 months ago

It was a very spacious and comfy home and we were welcomed very friendly even tho we arrived pretty late. The breakfast is also a very big plus at this apartment and the view of course …! Thank you for having us. :)

Guest favorite

An outdoor pool is framed by stone walls, reflecting the colors of the sky at sunset. Lush green fields surround the area, and a distant view of houses and hills can be seen in the background.

Home in Açores

5 out of 5 average rating, 6 reviews

Casas da Prainha B

AnzorRating, 5 stars1 month ago

Amazing house, very stylish and well decorated, beautiful views of the ocean, very quite and private location. Beautiful hike that you can start right from the house. Highly recommend!