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Vacation rentals in São Mateus da Calheta

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Top-rated vacation rentals in São Mateus da Calheta

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

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Guest favorite
A spacious bedroom features a comfortable bed with crisp white linens, flanked by bedside lamps. Original stone arches create a stunning window frame, allowing natural light to fill the room. A wooden tray rests on the bed, ready for morning refreshments.
Apartment in Angra do Heroísmo
4.86 out of 5 average rating, 79 reviews

Ocean - Casa Sao Joao - 4 Star Tourist Apartments

Located in the center of Angra do Heroísmo, overlooking the ocean, Casa São João is one of the oldest, noblest and most emblematic houses in the city. Recently restored, this mid-19th century architectural jewel, accented with original stonework, arches and columns, combines the romantic charm and charisma of it’s history with the comfort, refinement and convenience of the 21st century. With a bold decor, fusing contemporary and classic elements, all spaces, from the penthouse, to the suites, to the interior garden, were designed to guarantee comfort, serenity and delight to its occupants, typically families, who can find here a home far from home. The inner peace of its nooks are just a few steps away from the bustle of the historical city or the contemplation of the sea and of Angra´s bay, given its well appointed location. It's history dates back to the 1400s, the restoration revealed and maintained the original stone work inside and out. You will be welcomed into a lovely reception area and given access to your private suite. Spacious, modern, and an architectural treasure this suite features 2 generous bedrooms 2 bathrooms and open concept lounge, dining and kitchen area. We also offer free wifi and 120V outlets for our North American guests, no transformers are required.

Top guest favorite
A light-filled studio space is divided by a wooden partition, creating a sense of separation. A spacious bed is framed by two bedside tables, each featuring a reading lamp. In the background, a kitchenette is visible, set against a marble backsplash.
Condo in Angra do Heroísmo
5 out of 5 average rating, 18 reviews

AngrA+ | Studio with terrace with sea/city view

O Apartamento 02 está incluído num complexo de 6 apartamentos, o AngrA+. É um apartamento T0 (estúdio) com entrada individualizada do complexo. Tem 35m2 num espaço aberto e amplo, correspondente à antiga cozinha do edifício. Tem um terraço privativo com 23m2 dispondo de mesa e cadeiras com vista sobre o Monte Brasil. Para uma ocupação máxima de 2 pessoas. Os espaços comuns incluem um jardim, uma pool exterior, um salão com biblioteca e lareira, uma esplanada e uma lavandaria self-service.

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, 118 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
Rolling green hills meet the coastline in this scenic view. The image captures two prominent, gently sloped hills, framed by lush vegetation. A small structure with a red roof is visible in the foreground, and the horizon showcases the distant sea against a light sky.
Home in Angra do Heroísmo
4.94 out of 5 average rating, 219 reviews

Aunt Arlete's House

Traditional house, restored according to this concept, located in the city of Angra do Heroísmo, on Terceira Island, a UNESCO World Heritage Site since 1983. About 300 meters from the historic center and 500 meters from the beach or bathing area. Small garden/orchard. Accommodation with the attribution of the Green Lodging Award by the Azores Regional Directorate for the Environment, since January 15, 2018. Certified adherent to the Clean and Safe seal.

Superhost
A scenic outdoor patio features a rectangular table adorned with a patterned tablecloth, accompanied by two folding chairs. The view captures the ocean and natural landscape, framed by nearby houses and distant hills under a clear blue sky.
Home in Feteira
4.5 out of 5 average rating, 12 reviews

Casa Avô São Miguel

This rustic house is located in a privileged place in the Parish of Feteira near the sea, surrounded by vineyards and other crops, fresh air, radiant sun, excellent space to rest and relax with the chirping of birds. From the patio, terrace and windows of the house we can have the stunning privilege of observing the sea, the Ilhéu das Cabras. The bathroom has a shower and all the utensils that go with it. This house accommodates up to 5 people.

Top guest favorite
A bright interior features four wooden stools arranged at a window-side counter. Large windows offer a view of the sea and rocky coastline, allowing natural light to fill the space. Light-colored flooring complements the subtle decor.
Cottage in Quatro Ribeiras
4.99 out of 5 average rating, 167 reviews

Casa da Baía das Quatro [House of the Bay of Four] - AL 1425

Recently rebuilt house, located in one of most beautiful bays in the Azores. Nestled on the slope of the Quatro Ribeiras, it offers a unique view of both the sea and the rocky escarpment of the bay. Fully equipped with two bedrooms (one suite), two bathrooms, an open concept kitchen and living room, heating stove, balcony and outside space with barbecue and fire pit. Free private parking. Clean and Safe seal. Get ready for an unforgettable stay!

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
The windmill features a circular stone structure with a textured grey facade, highlighted by a conical roof in a warm tone. Natural light filters from above, casting soft shadows on the surrounding concrete patio and steps, which lead to the entrance.
Farm stay in São Mateus da Calheta
4.73 out of 5 average rating, 15 reviews

Banana Eco Camp - Windmill

The Windmill of the Banana Eco Camp is located on top of the hill in the middel of banana and flower platantation. Here you can relax and enjoy nature with more than 2 hectares of field only for you. In this huge plantation you will have the cosy windmill with al the comfort from a home. In the early morning you will have the chance to see the sun rise. This windmill is equipped with an double bed, toilet, and shower.

Guest favorite
An outdoor balcony is showcased, featuring two simple white chairs and a small wooden table. The expansive ocean view is visible, with the sun setting over the water, creating a serene atmosphere. Glass railings provide an unobstructed sight of the landscape.
Condo in Feteira, Angra do Heroísmo
4.89 out of 5 average rating, 172 reviews

Casa Ariel (AL no. 1687)

NEWLY RENOVATED – Experience modern living in our beautifully designed condo, offering some of the most stunning views on the island. Nestled in Feteira, this home overlooks iconic ‘Ilhéus das Cabras’ to the left and majestic ‘Mount Brazil’ to the right, with open ocean views ahead—perfect for unforgettable sunsets.

Top guest favorite
Home in Praia da Vitória
4.95 out of 5 average rating, 79 reviews

Tree House - AL Pt Martins RRAL Nº449

Villa located 50m from the shoreline. Ample indoor and outdoor space with ocean front and back to the mountain with complete privacy. Ideal for relaxing, sea bathing, surfing, scuba diving, snorkelling, cycling, walking trails, birdwatching etc. All you need to feel at home and enjoy your stay in Terceira Island.

Top guest favorite
Home in Biscoitos
5 out of 5 average rating, 24 reviews

Biscoitos Top Ocean View | AC | Nature | Peaceful

A Truly Authentic Airbnb Stay — Local, Personal, Unique ✨ Wake up to the gentle sound of birds and the fresh Atlantic breeze 🌊 Relax in charming Biscoitos, famous for its Verdelho wine and natural lava rock pools — the perfect Azorean escape surrounded by nature. 🌿

Guest favorite
A balcony area offers a set of two loungers and a small table, providing a comfortable space to relax. The surrounding view includes green landscapes leading to the ocean, under a clear blue sky.
Loft in Biscoitos
4.89 out of 5 average rating, 187 reviews

Biscoito Bravo AL - Open Space [RRAL No. 1235]

Casa do Biscoito Bravo is a cozy accommodation close to the sea and several walking trails. It is located in the parish of Biscoitos, Terceira Island, overlooking the sea, a small garden with endemic, decorative and aromatic plants.

Popular amenities for São Mateus da Calheta vacation rentals