Holiday rentals with a pool in Ilha de São Jorge

Find and book unique homes with a pool on Airbnb

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.

0 of 0 items showing

1 of 3 pages

Guest favourite

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?

Superhost

Flat in Horta

4.5 out of 5 average rating, 8 reviews

VitaminSeaAzores - First Floor

Spacious first floor apartment with fully equipped kitchen, living & dining room for up to 6 persons. Each bedroom has a ceiling fan. Hidden pool area that may be shared with the second floor apartment renters OR request for private use. Same day laundry & other services for a fee. 30 min walk or 4 minute drive to downtown Horta. Ocean & Caldeira views. Heated outdoor shower. 16 person outdoor dining table and outdoor bar. Perfect for families or groups. Rent out 2nd floor on a separate listing!

Top guest favourite

Home in Madalena

5 out of 5 average rating, 5 reviews

Ocean View Pico

Com vista deslumbrante e acesso direto às míticas águas açorianas encontramos esta moradia de piso térreo que contempla uma sala de estar e jantar em espaço aberto com a cozinha e um corredor que separa a área social da zona dos quartos. Com um amplo pátio de cerca 1000m2 e uma frente de mar de 40 metros estamos a 20 metros da linha de água do oceano Atlântico, com churrasqueira, pergola e tanque, permite-lhe contemplar o oceano azul em comunhão com a natureza.

Guest favourite

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 favourite

Villa in Criacao Velha

5 out of 5 average rating, 11 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.

Superhost

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

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.

Superhost

Serviced apartment in Calheta

5 out of 5 average rating, 3 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

Home in Madalena

5 out of 5 average rating, 16 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

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.

Guest favourite

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!