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Vacation rentals in Madalena

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Top-rated vacation rentals in Madalena

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

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Guest favourite
A spacious terrace is equipped with three lounge chairs overlooking the harbor. The view includes the coastline, distant mountains, and the sea, with boats visible in the water. The terrace is sunlit, bordered by a low wall, and the surroundings feature varied rooftops.
Apartment in Madalena
4.8 out of 5 average rating, 56 reviews

Casa do Pico

It is a 2-minute walk to the Terminal of the boats that connect Pico Island to Faial and São Jorge Islands. A 1-minute walk to the Whale Watching Companies. 10-minute drive to the airport. Very close to the municipal swimming pools. Close to Bars and Restaurants. Apartment with lots of lighting and a high ceiling and a terrace with a magnificent view over the port of Madalena and the channel that connects the islands of Faial and Pico. This space is good for couples, business travelers, and families (with kids)

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
5 out of 5 average rating, 15 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 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, 199 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
An open living area is presented with a light-colored sofa facing a wall-mounted television. Circular woven art pieces adorn the white walls. A low coffee table is centered on a textured rug, flanked by two armchairs and a decorative floor lamp.
Condo in Madalena (Areia Larga area)
4.81 out of 5 average rating, 143 reviews

Casa do Cacto - 1-Bedroom Flat in Areia Larga

Our 1-Bedroom Flat is a stylish and comfortable accommodation for a couple or small group (3-4 people max) - it is located at one of the most beautiful seafront areas in Pico overlooking Faial island. Some of the best restaurants on the island are nearby, and the town centre is only 10mins away - all walking distance. The Landscape of the Vineyard Culture is only 15mins away (on foot), a beautiful walk especially at sunset! Find us on Instagram @casadocacto

Guest favourite
The image features a wooden structure with large glass doors, adjacent to a rectangular swimming pool. Surrounding trees and a clear blue sky enhance the serene outdoor setting. A jacuzzi and seating area are visible, situated on a stone patio beside the pool.
Cabin in Madalena
4.97 out of 5 average rating, 58 reviews

Quinta-Casa da Pipas Wine Cellar

Relax to the sound of nature in this calm and elegant space, enjoying a pool, Jacuzzi and sauna on a farm with a paradisiacal view of Vila da Madalena, the sea and Faial Island, and benefit from the pedestrian walks with a view of the Pico mountain. Our accommodations are located 2 minutes by car and 20 minutes on foot from Vila da Madalena, and include a bedroom with a double bed and a living room with a sofa bed. You can enjoy a sauna and a fire pit.

Guest favourite
A wooden table is set on a terrace, featuring two glasses of white wine and a bowl of mixed nuts. In the background, a marina is visible with boats docked along the waterfront, framed by palm trees and coastal buildings under a clear blue sky.
Home in Madalena
4.9 out of 5 average rating, 20 reviews

Casa do Porto @ house with a terrace facing the sea

Casa do Porto is located in Madalena do Pico by the shore of Porto Velho, 350 meters from Gare Marítima João Quaresma, 140 meters from Areia Funda Natural Pools and 200 meters from the village center, where you can find several services such as restaurants and supermarkets. This holiday home features a terrace with a privileged view of the sea and villa. Free Wi-Fi and free public parking are available within 100 meters.

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.
Vacation home in Madalena
4.96 out of 5 average rating, 161 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.

Guest favourite
An open-plan living area is presented, featuring a wooden ceiling and earthy yellow flooring. A dining table with yellow chairs is visible, alongside a kitchenette equipped with essential appliances. Bright natural light filters through large windows, creating a warm and inviting space.
Home in Horta
4.95 out of 5 average rating, 129 reviews

Casinha Pim - Front of Beach/city house

Casinha em frente à praia de Porto Pim, com uma vista incrível e bem equipada. A 5 min. a pé do centro da cidade Tem TV cabo e Wi-Fi. Estacionamento gratuito perto de casa e espaço para guardar as suas bicicletas dentro de casa. Situa-se num antigo bairro de pescadores de frente para a baía e praia de Porto Pim e para o Forte de São Sebastião, muito agradável, tradicional e muito muito calmo.

Superhost
A modern kitchen is showcased, featuring dark wood cabinets and sleek black countertops. Stainless steel appliances, including an oven, microwave, and kettle, are visible. Light-colored tiles adorn the walls, while a small window offers natural light, enhancing the functional space.
Townhouse in Madalena
4.68 out of 5 average rating, 87 reviews

Pico Island Townhouse

Townhouse on the island of Pico in Madalena, the largest city on the island. Walking-distance to the shore, market, and town-center. Very pretty views of the ocean and island of Faial from the front of the house and a small private backyard. All new mattresses installed July 2025!

Top guest favourite
An aerial view showcases a stone house surrounded by lush greenery and terraced gardens. A private heated pool is centrally located within a well-maintained lawn, complemented by outdoor seating and parking space along a circular driveway.
Cottage in Santo Amaro - S. Roque do Pico
4.95 out of 5 average rating, 115 reviews

Casa do Caisinho Pico - Heated pool near sea

Stay in a dream lava home with a heated outdoor pool and an incredible sea view. Close to the sea, this lava house was fully restored from the ruins of a hundred-year-old lava house. We just installed the pool heating system so that, even in Winter, you can have a swim - Bliss!

Guest favourite
A welcoming living area is presented with a light gray sofa and a blue couch, each adorned with decorative pillows. A wooden coffee table is centered on a patterned area rug, with natural light filtering through sheer curtains that frame a nearby window.
Apartment in Madalena
4.96 out of 5 average rating, 23 reviews

SanMar

SanMar- Accommodation in the picturesque centre of Vila da Madalena, close to the main sights and communication routes. Located in the center of Vila da Madalena, it is close to the hypermarket, restoration, police entities, taxi stands, maritime gare and all services.

Top guest favourite
A terrace area is visible, featuring a gray overhang and a wall of dark stone. A lamp hangs from the structure, and green shutters complement the white-framed window. The ocean can be seen in the background, with soft hues of sunset lighting the sky.
Home in Madalena
4.95 out of 5 average rating, 77 reviews

typical Pico house, rustic and modern style

gosto muito do espaço da casa, muito confortável ... com uma bela esplanada com vista para o Oceano Atlântico e para o ponto mais alto de Portugal, Montanha do Pico.

Popular amenities for Madalena vacation rentals

Quick stats about vacation rentals in Madalena

  • Total vacation rentals

    Explore 80 vacation rentals in Madalena

  • Nightly prices starting at

    Madalena vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,950 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    80 of Madalena vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Madalena rentals

  • 4.8 Average rating

    Madalena stays are highly rated by guests—averaging 4.8 out of 5!

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