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Vacation rentals in São Mateus da Calheta

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Top-rated vacation rentals in São Mateus da Calheta

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Superhost
Two hands are shown forming a heart shape against a backdrop of the ocean. The vibrant blue water meets a rocky shore, with green grass and a path visible in the foreground, highlighting the natural beauty of the coastal setting.
Apartment in São Mateus da Calheta
4.9 out of 5 average rating, 10 reviews

Life on Quinta do Mar - New Oceanfront Oasis

AL apartment with breathtaking panoramic views of the ocean, Negrito Bay and Monte Brasil, located within a private oceanfront condominium. Accommodations are equipped with all modern conveniences such as, air conditioning in every room, Wi-Fi, 180 TV channels, full kitchen, washer and dryer, separate dining area, two bathrooms and private parking for two cars. Conveniently located in the town of São Mateus, just ten minutes from Angra do Herosmo, only two minute walk from the Negrito Bay area.

Top guest favorite
Two comfortable chairs are positioned on the grassy shore, overlooking a rocky coastline and the vast ocean. A small wooden table sits between them, inviting relaxation while enjoying the scenic view of the water and distant landforms under a clear blue sky.
Condo in S.Mateus
4.99 out of 5 average rating, 120 reviews

qMc - quinta do Mar, apart. C

Alojamento local (AL) certificado n.º1435. Apartamento em condomínio privado, sobre o Oceano, na zona marinha do Negrito, São Mateus da Calheta, a 10 min de Angra do Heroísmo (cidade património Mundial). Exclusivo a quem procura a qualidade, tranquilidade, comodidade e segurança, no meio de um ambiente natural, com excelente vista de Mar, montanha e acesso privado à zona marinha do Negrito Exposição solar a Este e Sul, vista para o Negrito, Monte Brasil e Oceano.

Guest favorite
Home in São Bartolomeu de Regatos
4.96 out of 5 average rating, 28 reviews

CASA DA EIRA

Casa da Eira is a country house, inserted in the rural environment of vegetable gardens and animals. It is located in the parish of São Bartolomeu, 5 minutes from two seaside resorts, the port of Cinco Ribeiras and Negrito, and 10 minutes from the World Heritage city of Angra do Heroísmo. With a large space, with a garden, vegetable gardens, a barbecue area and even a chicken coop, where you can observe our chickens and taste the wonderful eggs they lay.

Superhost
Apartment in Angra do Heroísmo
4.73 out of 5 average rating, 11 reviews

City House 1 by PontaNegraAzores

The City House 1 is a modern and comfortable accommodation, ideal for families or groups looking for a stay in the centre of Angra do Heroísmo, while benefiting from a calm environment sheltered from the hustle and bustle of the city. Its privileged location allows easy access to shopping areas, restaurants and main points of interest.<br><br>The accommodation consists of a bedroom with a double bed, a bathroom and an open-plan living room with a kitchen.

Superhost
Villa in Terceira
4.85 out of 5 average rating, 119 reviews

Serreta Island Home AL #1 (Premium)

Serreta- Island Home #1 is a fully equipped and restored XIX century country house situated in the smallest and most rustic parish in Terceira Island aligned with sustainable tourism (Miosotis Azores certification) and safe cleaning procedures (Clean and Safe Azores certification). It has all you need to disconnect and enjoy the real Azores vibe. It is surrounded by a 6000 square meters garden space with a perfect sea, sunset and country view.

Superhost
Cabin in São Mateus da Calheta
4.87 out of 5 average rating, 67 reviews

Banana Eco Camp - Cabin - Banana

Banana Eco Camp is a Glamping located in the middle of a banana plantation. Here you can relax and enjoy nature at its finest. The campsite also has its own organic coffee shop. There is a lot within walking distance, such as the city of Angra do Heroísmo, restaurants and seaside pools. This cabin is equipped with one double bed with an outdoor shared kitchen and toilet In the glamping are BBQ, campfire areas and outdoor hanging nets.

Top guest favorite
Two rocky islands emerge from a misty sea, their rugged shapes contrasting with a calm, deep blue ocean. Soft clouds drift above, reflecting the tranquil atmosphere of the surrounding landscape.
Home in Angra do Heroísmo
4.94 out of 5 average rating, 118 reviews

Breathe Nature - Beach House Azores

Relax in this Unique and Peaceful stay at Beira-Mar, a house inserted in the area of ​​Cultivation of Vineyards, which will take you back to a time when locals moved to Traditional Wineries, in order to take care of the vineyards, enjoy the sea ​​and the unique landscape. A unique house, with lots of character and love for details. This house is close to the Zona Balnear (two minutes walking). license number 831/AL

Superhost
A charming stone house with a tiled roof is situated along a cobblestone path. Lush green grass surrounds the structure, with ocean views visible in the background. The landscape features a mix of natural stone walls and vegetation that enhances the tranquil setting.
Loft in Angra do Heroísmo
4.86 out of 5 average rating, 7 reviews

Brown House - Simplicity, privacy, pleasure

Tucked away at the far end of the estate, The Brown House is our most private villa — a secluded retreat for those who value silence, space and exclusivity. Surrounded by nature, it offers a unique sense of calm, far from everything. Picture yourself unwinding with a book and a glass of wine, as the fireplace softly crackles — the kind of quiet luxury that makes Pico da Vigia unforgettable.

Superhost
A charming outdoor seating area features a wooden pergola, offering shade while overlooking a picturesque bay. Boats are visible in the calm water, with a green hillside in the background under a clear blue sky.
Home in S.Mateus
4.7 out of 5 average rating, 83 reviews

Ocean Front/Terraced House

Immerse yourself in the local culture while staying in this elegant and newly restored home, on Terceira Island- Azores. This scenic property offers panoramic ocean views, sight line to Mt. Brazil and the quaint town of Sao Mateus. Located atop a tall sea wall that resembles a fortress with it's well appointed large balconies, spacious patio seating/dining areas and magnificent views.

Guest favorite
Apartment in Angra do Heroísmo
5 out of 5 average rating, 6 reviews

Cozy loft with mezzanine in Angra’s city center

★ Porta da Sé - C (RRAL 4810) by Check in Azores Charming loft with a double bed on the mezzanine, a sofa bed, and windows facing the main street. Features air conditioning, TV, equipped kitchen, and bathroom with amenities. Well-built, quiet, and comfortable — right in the city center. Perfect for couples or small families. Book now and feel at home in the Azores.

Superhost
A rustic duplex property displays a mix of white walls and colorful accents beneath a partly cloudy sky. Lush greenery surrounds the building, highlighting a large round fire pit in the yard. Stone pathways lead to an inviting outdoor seating area with white chairs.
Tiny home in Angra do Heroísmo
4.69 out of 5 average rating, 121 reviews

Studio Lua Nova

Annex/Independent and isolated studio, which develops on two floors in a duplex/open-space perspective, integrated in the property where I live regularly. Situated in a quiet area, enjoying the proximity of animals (dogs, horses, various birds,...), about 5 km from the city of Angra do Heroísmo and with the possibility of parking inside the walled space.

Top guest favorite
The modern chalet is set amidst lush greenery, showcasing a combination of stone and wood elements. Large glass doors provide an open view of the surrounding nature, while the elevated structure offers a glimpse of the terraced garden below.
Chalet in Biscoitos
4.98 out of 5 average rating, 81 reviews

Casa do Moledo, Outeiro, Biscoitos AL RRAL Nº802

Mountain Chalet located on the highest point of the hillside of the Biscoitos village, surrounded by orange groves, grasslands with cows, sheep and Atlantic Forest, at 5 minutes’ drive from the coast and the famous natural pools and Protected Landscape of Wines Biscoitos Area. Ideal for relaxing, swimming, snorkelling, hiking trails, bird watching, etc.

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