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Holiday houses in Caloura

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Top-rated holiday rentals in Caloura

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

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Top Guest favourite
A bright outdoor dining area is presented with a glass table, surrounded by six blue chairs. Plates and beverages rest on the table, suggesting a meal in the open air. The ocean is visible in the distance, framed by lush greenery and clear blue skies.
Home in Lagoa
4.98 out of 5 average rating, 169 reviews

Chestnut tree

Welcome to Castanheiro. Our property is a recently refurbished house built around a century old chestnut tree. A spacious terrace offers a panoramic view of the Santa Cruz Bay. It is conveniently located in Lagoa and within a 3 min walking distance to the ocean . A stroll to natural swimming pools will take you 10 min. The house was lovingly restored to maintain its original stone features. A perfect place to enjoy with family and friends as it comfortably accomodates up to 6 people.

Top Guest favourite
Windmill in Povoacao
4.95 out of 5 average rating, 185 reviews

Waterfall Life: immersed in secluded nature

A converted stone watermill at the bottom of a small valley, between two waterfalls. Walking in, you half-expect to have stepped back a century. The sound doesn't stop—it follows you to sleep and is the first thing you hear in the morning. You leave the car on an old bridge above and walk down a short rustic path; below it, the property opens up. Two villages and a small market sit a hundred meters back, reminding you civilization is still out there—but down here you're in your own world.

Guest favourite
A well-constructed cabin with a curved roof and wooden exterior is positioned near the edge of a lush landscape. The expansive ocean views are visible in the background, complementing the serene surroundings. Stone pathways lead to the entrance, framed by green shrubs and plants.
Cabin in Lombinha da Maia
4.98 out of 5 average rating, 41 reviews

Designer Cabin Retreat with Ocean Views

Top 3 Guest Compliments: "My partner and I got engaged on the balcony overlooking the ocean." “The cabin is perfectly secluded…we felt like we were in our own bubble!!" "Hosts go above and beyond with thoughtful guidebooks and local treats." From the moment you arrive, you’ll feel the weight lift off your shoulders. Handcrafted from local woods and inspired by Japanese design, this retreat sits in a 5,000m² private garden—perfect for couples or anyone seeking to reconnect with nature.

Top Guest favourite
The exterior of a modern cottage is visible, constructed with natural wood and featuring large windows. It is surrounded by a serene landscape, with lush greenery and a view of the calm lagoon in the background. A wooden deck with a seating area is present.
Cottage in Sete Cidades
4.99 out of 5 average rating, 150 reviews

Sete Cidades Lake Cabin - Luxury Lakefront Cabin

New, charming and comfortable 'Cottage' (with 2 en-suite bedrooms) right on the shores of Lagoa das Sete Cidades. The project, the design and the materiality were carefully conceived for a perfect setting in the surrounding nature and in order to benefit from stunning views of the Lagoon. Situated in a unique landscaped environment, where the calm and tranquility of the natural environment predominates, it also benefits from all the amenities and comfort to make your stay unforgettable.

Guest favourite
Guest suite in Agua de Pau
4.92 out of 5 average rating, 100 reviews

VILA BELA - Sea Suite

Guest House: My space is at the top of the property, with access by ramp or stairs (with 38 steps), close to Baixa d'Areia beach, Caloura port with a natural swimming pool, where you can bathe in the summer, a supervised area with a lifeguard, Bar da Caloura where you can enjoy good fish meals, there is also a Cultural Center in Caloura. You'll love my place because of the superb view of the sea, its location in the center of the island, and the gardens in the outdoor area.

Top Guest favourite
A modern dining area features a long wooden table surrounded by six chairs. A comfortable sofa sits nearby, positioned toward a wall-mounted TV. Large glass doors provide natural light and views of greenery from a private balcony.
Apartment in Lagoa
4.99 out of 5 average rating, 214 reviews

SARA invites you - Tecnopark Residence

The apartment «SARA conVida - Tecnopark Residence» is a new 2-bedroom apartment and is located in the city of Lagoa, next to NONAGON and CUF Azores Hospital. It is located in the center of São Miguel Island, which makes it very accessible to the island's various tourist attractions. It is located 10 km from Ponta Delgada and 1 km from a seaside hiking area, with natural pools. It is close to supermarkets, shops, cafes, restaurants of your choice and great seaside areas.

Guest favourite
A spacious kitchen area features a light green island counter and a dining table set for meals. Natural stone walls and a spiral staircase add character to the space. Soft lighting creates a welcoming environment, enhancing the connection between the kitchen and the dining area.
Home in Agua de Alto
4.97 out of 5 average rating, 148 reviews

ADEGA DO MOTA

Recovered house (old winery), integrated into a 5,000 m2 farm, with a wide variety of citrus and other crops. Great garden, overlooking the sea and the mountains. It has a very spacious social area, ideal for families and groups of friends, where there is a pool table. Very close to several beaches and the center of Vila Franca do Campo. There are several trails starting near the house. Located on the south coast of São Miguel Island, with easy access to Ponta Delgada.

Top Guest favourite
A modern living area features a comfortable sofa adorned with decorative pillows, alongside a stylish armchair. A round coffee table is placed centrally on a neutral rug. Light streams through large sliding glass doors, illuminating a well-organized shelf displaying decorative items.
Apartment in Ponta Delgada
5 out of 5 average rating, 162 reviews

Simple&Charming Guest Apartment

Simple&Charming é um apartamento com dois quartos, moderno e elegante. É ideal para viver o centro da cidade em qualquer época do ano. Dispõe de estacionamento gratuito para que possa visitar a nossa ilha durante o dia e viver a cidade durante a noite. Simple&Charming is a modern and elegant guest apartment with two bedrooms ideal for every time of the year. It offers free parking so you can travel around the island during the day and live the city by night.

Guest favourite
A covered walkway adorned with lush green vines offers shade along the white exterior of the building. Steps lead up to an elevated area, with surrounding greenery providing a natural frame for the setting.
Guest suite in Agua de Pau
4.9 out of 5 average rating, 71 reviews

The Vineyard House

The designation Casa da Vinha evokes the winemaking activity that, until half a century ago, characterized this property. Thanks to the micro-climate of Caloura, the vineyard, protected from humidity and fog, produced grapes for many years. In Casa da Vinha, as in all properties, large or small, there was a building, in stone, covered with tile, the so-called winery, to store the wine produced, and now is ready to accommodate guests.

Guest favourite
A modern suspended living room with expansive glass walls hovers above a small garden and outdoor dining area. The contrasting white exterior of the house highlights the sleek, black cube design, creating a unique architectural feature against the backdrop of blue skies.
Home in Vila Franca do Campo
4.87 out of 5 average rating, 344 reviews

House with Suspended Living Room

Our Retreat is a rural nineteenth-century house, restored with the desire to conserve the time of construction characteristics. Not only did we keep the main structure of the house, but also the fire oven and the respective chimney, the mill of wine production and the basalt stone floor . And, to finalize we added a suspended living room - literally a glass cube.

Top Guest favourite
Home in Agua de Pau
5 out of 5 average rating, 11 reviews

Modern house, one bedroom, sea view in Caloura

Relax in this peaceful cocoon nestled between green hills and Atlantic waves, on the island of São Miguel. At Ann's Paradise, everything invites you to slow down: breakfast in the sun, naps to the sound of birdsong, evenings rocked by Cory's shearwaters... Modern comfort and island authenticity mingle with simplicity. Great for a solo or couple stay.

Top Guest favourite
The exterior of Galera Cottage is visible, showcasing its traditional architecture with green shutters. A view of the ocean is framed by a tree with bare branches, while colorful plants and well-maintained grass surround the property, enhancing the serene atmosphere.
Cottage in Caloura
4.99 out of 5 average rating, 136 reviews

Galera Cottage – RRAL761

Located in Caloura, one of the most iconic and idyllic spots of S. Miguel island, Galera Cottage offers its guests a unique view over the sea, proximity of bathing areas, priceless tranquillity, and the possibility to visit the seventeenth century chapel of Nossa Senhora de Monserrate, located inside the propriety.

Popular amenities for Caloura holiday rentals

  1. Airbnb
  2. Portugal
  3. Azores
  4. Caloura