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Holiday rentals in Calhetas

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Top-rated holiday rentals in Calhetas

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

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Guest favourite
An expansive view of the ocean is captured from the property, framed by lush greenery. A tranquil pool reflects the sky, while a deck area with seating encourages outdoor relaxation. The horizon is adorned with scattered clouds, enhancing the coastal atmosphere.
Home in Mosteiros
5.0 out of 5 average rating, 10 reviews

Villa Anna

We present to you an modern villa built in 2024 with stunning sunset and panoramic ocean views. The villa is located on a private 0.5 hectares of land with its own garden, terraces and outdoor pool (12m) with salt water. The area of the house is 350m2. Seaview terrasses and patio 300 m2. Ceiling height is 4 meters. This house consists of 3 sleeping areas, each with its own dressing room and its own bathroom. The large living rooms have a dining areas with fireplace and a TV areas. 4 bathrooms.

Top guest favourite
Windmill in Povoação
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.

Top 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 Maia
4.98 out of 5 average rating, 43 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.

Top guest favourite
Home in São Roque
5.0 out of 5 average rating, 12 reviews

Villa São Roque - Cocoon by the sea

Villa São Roque is a modern house, built from scratch and located on the waterfront, in a quiet area of the typical São Roque neighborhood. With spacious and functional interiors, it stands out for its pleasant outdoor spaces: a saltwater pool and several areas designed to relax and enjoy the view over the Atlantic. Right at the door of the Villa, in the small bay in front, you can fish on the rocks, swim in the natural ocean pool or enjoy the tiny beach next to the islet.

Top guest favourite
Home in Calhetas
5.0 out of 5 average rating, 13 reviews

Ocean Dreams Place

Make the most of it and come and try out this new space for your well-deserved holiday. Our accommodation is located in the central part of the island, allowing you to explore all the beauty of São Miguel with the utmost ease. It's the ideal setting for those looking for a relaxing holiday. Our accommodation combines traditional Azorean charm with the functionality needed for a refreshing stay. Come and enjoy an authentic experience in the Azores!

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.
Flat in Ponta Delgada
5.0 out of 5 average rating, 163 reviews

Simple&Charming Guest Apartment

Simple&Charming is a modern and stylish two-bedroom apartment. It is ideal to live the city center any time of year. It offers free parking so you can visit our island during the day and live in the city during the night. 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 sunny, yellow cottage is framed by lush greenery, with climbing plants adorning the entrance. A wooden bench provides seating on the grassy lawn. Inside, light filters through the doorway, hinting at a well-lit interior. The scenic views of fields and the ocean are visible in the distance.
Cottage in Ajuda da Bretanha
4.93 out of 5 average rating, 472 reviews

Welcome to A Toca do Lince I

Countryside cottage in the northwest of São Miguel, with views to the ocean, the mountains and the fields. An option for those who want to explore the main attractions of the western part of the island, but wish to stay in a place off the beaten track. PLEASE NOTE THERE IS A CAT living in the cottage, she's an INDOOR/OUTDOOR CAT. If you don't like cats or are allergic to them, the cottage is not a suitable option for you.

Guest favourite
A balcony features a wooden table set for two, with glasses of drink placed atop. The ocean and fishing port are visible in the background, complemented by a clear blue sky. Natural elements like plants add a touch of greenery to the setting.
Home in Lagoa
4.88 out of 5 average rating, 155 reviews

azoresstays-Villa Sal over the sea & natural pools

This ocean cliff Villa and its spacious rooms have a lush ocean view and you will have a completely clean and unique view of the sea, Lagoa's picturesque fishing port and natural swimming pools. You can not find a more central place to stay, with all the amenities walking distance. Local restaurants with lots of fresh fish, grocery and supermarkets, pharmacy, bathing areas and even a gym.

Superhost
A spacious outdoor area is featured, showcasing a well-maintained lawn with several white loungers arranged around. The charming house is adorned with red shutters and white walls, complemented by surrounding greenery and a stone wall, creating a serene environment.
Home in São Miguel
4.86 out of 5 average rating, 86 reviews

Home Sweet Home

Located on the north coast of São Miguel Island, Home Sweet Home is the ideal home for families looking for space and comfort to enjoy a relaxing vacation. The house is a 15-minute drive from the airport and 10 minutes from the beautiful Santa Bárbara beach, ideal for surfers. On the ground floor, there is a mini-market that has all the essentials.

Guest favourite
A historic windmill stands prominently against a clear blue sky. The structure features distinctive red blades and a white base, complemented by a bright red door. Lush greenery and cobblestone paths surround the mill, enhancing the scenery.
Windmill in Ponta Delgada
4.91 out of 5 average rating, 350 reviews

Moinho das Feteiras | The Mill House

Built in the 19th century, with a 360 degrees view over the sea and surroundings on the top floor. It features a Bedroom, a very well-decorated living room with kitchenette, and a WC. Free WiFi, air conditioning, Led TV and DVD player. Private parking inside the premises, providing extra security. Perfect for an unforgettable honeymoon experience.

Guest favourite
Home in Ponta Delgada
5.0 out of 5 average rating, 6 reviews

Luxury Beach House

Exceptionally located between two south coast beaches with cafes and restaurants within a short walk. Luxury Beach House is the perfect place for families or friends to enjoy a unique holiday experience in Sao Miguel, Azores.

Popular amenities for Calhetas holiday rentals

  1. Airbnb
  2. Portugal
  3. Azores
  4. Ilha de São Miguel
  5. Calhetas