Holiday houses in São Joao

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Top-rated holiday rentals in São Joao

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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 S.Roque do Pico

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?

5.0 out of 5 average rating, 43 reviews

Guest favourite

A traditional island home features white walls and a red-tiled roof, accented by red window shutters. The house is set against a backdrop of a prominent mountain, with a clear blue sky overhead. Lush greenery surrounds the property, providing a natural setting.

Home in São João

PeakWithMe

We got to know Pico and fell in love with the island. We bought a house and went to live on the island. We rented the entire house on the 1st floor and lived in an apartment on the property. As travelers, we respect the privacy of our guests. It is a traditional house on the island, with all the charm of a typical Pico house, but with all the comforts for a family vacation. Sea and mountain view 300 meters from the Arinhas bathing area and with the São João trail just 30 meters from the house.

4.85 out of 5 average rating, 34 reviews

Top Guest favourite

A spacious living area features large glass windows that offer views of the sea and mountains. A round wooden dining table is surrounded by four white chairs. A comfortable seating arrangement includes a grey sofa and a rocking chair, under a vaulted wooden ceiling.

Home in Prainha

Nemo's Corner

We are a Portuguese family that knows all the islands of the Azores, and completed in August 2018 this retreat, to get away from our busy lives in London. Until the day comes that we can enjoy it full time, we have decided to share the amazing space we have created with others that love the nature, mountain and sea that is always surrounding us. The house is within Prainha, the most beautiful parish of Pico Island, and within close proximity to the beach, restaurants, grocery store and bakery.

5.0 out of 5 average rating, 33 reviews

Guest favourite

A terrace is showcased with two sun beds positioned for relaxation, overlooking unobstructed ocean views under a clear blue sky. The modern structure features sliding glass doors that lead inside, complementing the natural coastal environment.

Home in Ribeira Grande

Casa Oceano Pico

Casa Oceano Pico is a new, modern house nestled in one of the most beautiful and serene parts of the island, offering peace, tranquility, and lush greenery. With fabulous, unobstructed views of the Atlantic Ocean, you’ll find yourself immersed in natural beauty. Located just a 15-minute drive from the picturesque town of Lajes do Pico, and close to some of the island's most stunning natural pools, this home is ideal for solo travelers, couples, friends, families, and remote workers alike.

4.94 out of 5 average rating, 36 reviews

Guest favourite

Home in Canto da Areia

House by the sea

Designed from the ground up with comfort and calm in mind. With clean lines, warm materials, and wide-open views, the house invites you to slow down and soak up Pico’s natural beauty — from the private jacuzzi under the stars to the soft silence of the mornings. Whether you’re here for a romantic escape or a laid-back family adventure, this space adapts to your pace. It’s intimate, spacious, and just far enough off the map to feel like your own private piece of the island.

5.0 out of 5 average rating, 15 reviews

Top Guest favourite

An aerial view captures the tiny homes nestled in a lush green landscape, surrounded by well-maintained gardens and rocky walls. The ocean is seen in the background, with expansive views extending to the horizon and the island of São Jorge, creating a sense of tranquility.

Cabin in Santana

Casinha Melissa

What you can expect at Casinha Melissa: • queen-size bed with memory foam mattress • USB/USB-C ports built-in to the light socket at each bedside table • 43" Smart TV for streaming on all major apps or watching cable • WIFI connection with high-speed internet • ceiling fan • air-conditioning/heating system • private on-site laundry with steam dryer option or clothesline located behind the house (clothes pins provided) • personal picnic table • firewood for the fire pit

5.0 out of 5 average rating, 24 reviews

Top Guest favourite

Villa in Santo António

Pico Sereno · Casa Atlântico | Sea & Nature View

Cozy and quiet studio in the heart of Pico Island, between Madalena and São Roque, just minutes from the airport. Ideal for couples or travelers looking for rest, nature and easy access to the entire island. It has a comfortable double bed, private bathroom, Wi-Fi and free parking, with access to outdoor common areas. Located in a quiet area, perfect for relaxing after a day exploring trails, bathing areas, vineyards and viewpoints. Ideal for couples, quiet stays.

5.0 out of 5 average rating, 19 reviews

Guest favourite

Cabin in São Roque do Pico

Casa da Camélia

Charming country house overlooking the village of São Roque do Pico, the Canal between Pico and São Jorge and the neighboring island of São Jorge. This house is a haven of tranquility, simplicity. Enjoy quiet days in this charming country house surrounded by nature. Ideal for those seeking rest, silence and beautiful landscapes. The house offers a cozy atmosphere with simple decor, ample outdoor space and perfect areas to relax outdoors.

5.0 out of 5 average rating, 15 reviews

Guest favourite

An open-plan living area features a spacious gray sofa and a dining table surrounded by black chairs. A modern kitchen with dark cabinetry is visible in the background. Natural light floods the space through large windows, highlighting the wooden ceiling and sleek staircase.

Home in Prainha

Adega do Cagarro

Adega do Cagarro is located in Prainha, one of the most beautiful parishes on the island of Pico. It has 2 bedrooms, 1 bathroom and a fully equipped kitchen. Outside there is a terrace, barbecue and a magnificent view of the sea and the island of S. Jorge. It also has free private parking. The sandy beach, unique to Pico Island, is about 5 minutes away and can be easily reached on foot, enjoying a breathtaking landscape.

4.89 out of 5 average rating, 28 reviews

Guest favourite

A kitchen area is presented with wooden cabinets and a dining table surrounded by four chairs. The geometric-patterned wallpaper adds a modern touch, while stainless steel appliances include a refrigerator. A staircase with wooden steps leads to the upper level.

Home in Madalena

Grandfather Francisco's House

Once a traditional wine cellar, built by Francisco Paulo in 1980, this villa served for many years as a production site and warehouse for the Paulo family's wine. The wine cellar has been remodeled and expanded, but it maintains the traditional elevations and the decoration and details of the times when it was used as a wine cellar. Next to the bathing area, it has a view that invites long nights of conversation.

4.95 out of 5 average rating, 122 reviews

Top Guest favourite

Home in Terra do Pao

Mysteries Lodge

Misterios Lodge is a quiet, private retreat designed exclusively for adults seeking calm and privacy. Set among trees with Atlantic views on Pico Island, it is a single-level, high-quality lodge built from sustainably sourced wood and designed for thermal and acoustic comfort. The lodge is intended for guests who value quiet surroundings and a low-noise environment and is not suitable for parties or events.

5.0 out of 5 average rating, 16 reviews

Top Guest favourite

An outdoor terrace showcases a wooden dining table surrounded by four chairs. A vase filled with dried flowers sits at the center, with a backdrop of lush green hills under a clear blue sky.

Home in Ribeiras

House of the Two Rivers

Casa das Duas Ribeiras is a cozy Azorean house made of local lava stone, ideal for relaxing in the heart of nature on Pico Island. It offers peaceful accommodation with modern amenities, a garden and ocean views. The house is suitable for couples looking for privacy, style and the authentic atmosphere of Pico Island.

5.0 out of 5 average rating, 33 reviews