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Holiday houses in Rua dos Caldeiroes

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Top-rated holiday rentals in Rua dos Caldeiroes

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

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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 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, 227 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.

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
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
5.0 out of 5 average rating, 24 reviews

PicoTerrace

PicoTerrace, a unique place! Comfort and design, with a panoramic view. Located in Madalena, it offers a garden, barbecue facilities and a terrace, with private parking on site and free Wi-Fi access. The Villa includes 2 bedrooms with a double bed and the possibility of installing a sofa bed, a living room, cable TV, an equipped kitchen and a bathroom with a whirlpool bathtub and shower. Enjoy the moments!

Top Guest favourite
A traditional wine house with red accents is framed by dark lava stones, set against the backdrop of Pico Mountain, topped with snow. A clear sky with a visible moon enhances the serene landscape, inviting guests to experience the uniqueness of the surroundings.
Holiday home in Madalena
4.95 out of 5 average rating, 170 reviews

Ocean view in UNESCO Heritage Site

Solar-powered wine house located in the Landscape of Pico Island Vineyard Culture - a UNESCO World Heritage Site. Just a couple of minutes driving from Madalena village, this traditional and remodeled wine house has its own vineyard on the backyard. A cozy space for two with a bedroom, kitchenette open to living room and a bathroom. The wine house is overlooking the ocean, Faial island and Pico mountain.

Guest favourite
An expansive property features multiple wooden structures with terracotta roofs, surrounded by lush greenery. An outdoor area includes a pool, providing a serene view of a distant mountain under a cloudy sky, enhancing the tranquil landscape.
Villa in Madalena
4.93 out of 5 average rating, 14 reviews

Alma do Pico - T0 House

"Alma do Pico" is a tourist village, known as a nature resort. It is a tranquil village, integrated into nature, with units scattered throughout the property, connected by gardens and paths. Relaxing atmosphere, ideal for couples, families and travelers seeking peace and quiet. Stunning views of the mountain and Faial Island.

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.

Guest favourite
Cottage in Calhau
4.85 out of 5 average rating, 144 reviews

Casa do Cais

You will find this holiday home at Porto Calhau - only a 10 minutes drive from Madalena. There is one big bedroom for 5 people ( 1 double bed, and a bunk bed for 3 people), one living room with a kitchenette, bathroom with a shower and a toilette. It also has a terrace where you can enjoy beautiful sunset.

Popular amenities for Rua dos Caldeiroes holiday rentals