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Holiday houses in São Mateus

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Top-rated holiday rentals in São Mateus

Guests agree: these stays are highly rated for location, cleanliness and more.

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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
5.0 out of 5 average rating, 43 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 favourite
Home in Ginjeira
5.0 out of 5 average rating, 7 reviews

Casa Next to a Volcano!

Welcome to Casa do Rico Pereira! Our small old-fashioned lava house has an amazing view amid a peaceful setting up on the hillside above the village of São Mateus. The Pico volcano looms behind our house, and the view overlooks the UNESCO-heritage vineyards down to an expansive view of the ocean. One small bedroom has a queen bed, and there is a sofa-bed that can sleep one person or two children comfortably. Come and relax on Pico, swim in the sparkling sea, wander the trails and footpaths!

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
5.0 out of 5 average rating, 31 reviews

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.

Superhost
A covered terrace features woven seating options with plush cushions and a glass-topped table. Lush greenery surrounds the area, while the sunset casts a warm glow in the background. Large windows allow for natural light to fill the space, creating an inviting atmosphere.
Cabin in São Mateus
4.79 out of 5 average rating, 112 reviews

The Wooden House - 5 guests, BBQ

Sea, Nature, Resort offers a 110m2 cosy home,fantastic ocean and mountain views, baby equipment, 40 sqm roofed terrace, Internet, 3 bedrooms (16m2): double + single, 3 single, 2 single beds, 10m2 bathroom + shower + tub, washing machine, tumble dryer, guest toilet, 50m2 living room/kitchen, dish washer, induction cooking, electrical oven, microwave, BBQ, natural swimming pool 400m distance. Hiking along coast/vineyards. Madalena port 20mins; Airport 30mins, S. Roque port 40 mins drive.

Top 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
4.94 out of 5 average rating, 33 reviews

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.

Top Guest favourite
A view of the sea framed by the open window, featuring two unique, bare trees on the shoreline. The calm water reflects the sky, while distant islands are visible on the horizon, creating a serene coastal scene.
Home in Madalena
4.96 out of 5 average rating, 225 reviews

Charming Beach House along the Ocean

Located minutes from downtown Madalena, “Casa da Barca” is a charming space granting guests picturesque views of the ocean and island of Faial from one side, and iconic Pico Mountain on the other. Walk only a few steps out the door and take a dip into natural pools or enjoy a refreshment at Pico’s award winning Cella Bar. Your host will welcome you with some cheese and wine, giving you a taste of the Acores and getting your palate ready for delicious island food.

Guest favourite
Villa in Madalena
4.94 out of 5 average rating, 18 reviews

Casa Baleia Laranja Oceanfront

Experience up close the sea pounding against the volcanic rock of Pico Island. Located on the north coast amidst the UNESCO World Heritage Site, this sea-level, ocean-front property is located 5 minutes by car from Madalena, the largest town and center for shopping on Pico Island. The house, with plenty of parking. sits on a landscaped 5500 square meter (approximately 1.3 acres) property, that also supports a small vineyard.

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
4.95 out of 5 average rating, 121 reviews

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.

Top Guest favourite
Home in Santo António
5.0 out of 5 average rating, 23 reviews

Pico Sereno · Varanda do Mar | Sea View & Balcony

Fully private 2-bedroom house with a balcony and a view of the Atlantic Ocean, located in a quiet area on Pico Island. Ideal for couples or small families looking for comfort, quiet, and a good location. It has comfortable rooms, an equipped kitchen, a private bathroom, Wi-Fi, and free parking. An excellent base for exploring trails, beaches, vineyards, and viewpoints, always returning to a quiet place to rest.

Top Guest favourite
Home in Terra do Pao
5.0 out of 5 average rating, 15 reviews

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.

Top Guest favourite
A historic house is depicted with white walls and a red-tiled roof, surrounded by lush greenery. Steps lead up to the entrance, and several windows allow natural light into the space. The backdrop features a mountainous landscape.
Home in São Roque do Pico
4.99 out of 5 average rating, 73 reviews

Latada House | Historic Azorean Home in Pico

Casa da Latada is a historic family home in Cais do Pico, São Roque do Pico. Spacious, cozy, and renovated, it offers a comfortable stay with a warm, authentic atmosphere. Preserving original details and generations of family history, the house blends traditional character with modern comfort — ideal for enjoying Pico Island in a genuine and welcoming setting.

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
5.0 out of 5 average rating, 33 reviews

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.

Popular amenities for São Mateus holiday rentals