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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
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 São Roque do Pico
5 out of 5 average rating, 41 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?

Top Guest favourite
An outdoor dining area is presented under a covered terrace, featuring a wooden table surrounded by several chairs. The view reveals a scenic coastline leading to the Atlantic Ocean, framed by rolling hills and distant mountains, illuminated by soft evening light.
Home in Santo Amaro
4.99 out of 5 average rating, 85 reviews

AtlanticWindow - Modern House, Stunning View

Pico Island, and especially Santo Amaro, has always been the holiday’s spot of our family. Here we grew up, we saw ships being built, we learnt how to swim, to fish and to live around nature. The dream of having our own place here, where to revisit the past, to rest and to enjoy the local genuine environment, has come true years later. The houses, built in a modern style, but with both inside and outside local stone details, were designed to take full advantage of the outstanding location an

Guest favourite
An outdoor jacuzzi is positioned beneath a wooden pergola, offering panoramic views of the surrounding landscape, ocean, and distant village. The clear blue sky and scattered clouds create a tranquil atmosphere, enhancing the unique setting for relaxation.
Cabin in Madalena
4.94 out of 5 average rating, 98 reviews

Adega da Quinta - Casa do Camolas

Relax in this cottage with a unique and tranquil 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 located 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.

Guest favourite
A cozy outdoor lounge area features a wooden pergola providing shade, overlooking a view of the coastal town and harbor. Comfortable seating is arranged on stone flooring, with potted plants and greenery accentuating the space.
Cottage in Horta
4.87 out of 5 average rating, 71 reviews

Casa Volta do Mar in Porto Pim, Horta

A lovingly restored fisherman’s cottage located in the sought after bay of Porto Pim, Casa Volta do Mar offers self catered accommodation with a stunning multi-levelled garden up the side of Monte Queimado, with views of the beach and Atlantic ocean to the right and to the left, the harbour in Horta where you can watch the sailing boats travelling in and out. This one bedroom cottage is the perfect place for couples to stay to enjoy the beauty of the natural landscape within the city of Horta

Top Guest favourite
A spacious living area features a light-colored sofa and a wooden coffee table crafted from natural materials. At the back, a dining table is set, surrounded by four chairs, with a minimalist kitchen visible in the background. Large windows provide soft natural light.
Villa in Conceicao
4.92 out of 5 average rating, 26 reviews

Sea view villa and beach access on foot

Relax in this unique and peaceful accommodation. Located in the valley of Almoxarife. 5 min walk to the most beautiful black sand beach of the island and 10 mins to the famous Horta marina and landmark downtown by car. Completely renovated, the house offers all modern comforts. All rooms have sea views. The villa "Quinta dos Maracujas" is a located on a vast orchard, where, depending on the season, you will be able to enjoy the exotic fruits. Bars and restaurants at the bottom of the street.

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
4.92 out of 5 average rating, 25 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 12-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.

Guest favourite
Home in Canto da Areia
5 out of 5 average rating, 6 reviews

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.

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
4.95 out of 5 average rating, 214 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
4.93 out of 5 average rating, 15 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
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, 166 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.

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, 67 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.

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
4.92 out of 5 average rating, 13 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.

Popular amenities for Rua dos Caldeiroes holiday rentals

  1. Airbnb
  2. Portugal
  3. Azores
  4. Ilha do Pico
  5. Rua dos Caldeiroes