9 of the most charming holiday homes and B&Bs in Madeira

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Not all holiday homes have the “x-factor” that gets us truly excited. That’s why we’ve trawled through hundreds of listings to find only the best holiday homes in Madeira.

Whether you’d like to stay in a cute country house, a boho chic apartment, or a funky surfer lodge, we believe these B&Bs and holiday homes in Madeira have a special vibe.

Did you know there are nearly 1000 properties in Madeira? With this curated list, we’ll help you take away hours of tedious browsing to find that adorable cottage you were dreaming of…

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ASPA – S茫o Paulo Studios

Location: Funchal

This studio apartment in Funchal definitely has a vibe, with a gorgeous terrace filled with plants and flowers. The rooftop gives perfect views of the fortress of S茫o Jo茫o.

The rooms all have a kitchenette which definitely comes in handy when you’re self-catering, though breakfast is already included.

The building includes three holiday apartments of different sizes, which are all part of the same small family-run hotel. Perfect for a couple and ideal if you’re looking for a charm hotel inside Funchal. The location is convenient with a supermarket and shopping center nearby, a parking lot for your car, and every part of the island being easy to reach from the capital.

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Casa do Vale

Location: S茫o Vicente

We stayed here — perfect for groups or families!

We loved our time in this house, which is very spacious and blessed with some stunning views of the S茫o Vicente Valley. Having four bedrooms, this vacation house has plenty of space for a family or group (we stayed here with two families).

The garden is ideal for babies or kids as it’s safely surrounded by fencing. Our baby daughter could play in the garden without us having to worry, and the living room has many games and books that can keep kids entertained. Oh, did I already mention the views are stunning?

This holiday home is located in S茫o Vicente, one of the most beautiful villages on the north coast. It can be reached from the airport in about 40 minutes.

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Calhau Grande

Location: Calheta (west coast of Madeira)

Comprised of six traditional Madeiran houses, Calhau Grande offers a rustic atmosphere on the sunny and calm side of western Madeira. Each cottage is equipped with a kitchen and all benefit from the shared pool, lush gardens, and ocean views.

You’ll be located just a short drive from Calheta Beach, a small sandy beach created inside the harbor of Calheta town. Since it’s sheltered, this is a great beach for families with kids. Don’t miss the charming village of Jardim Do Mar while you’re here.

We’ve noticed these cottages book out well in advance, so be sure to reserve early for a chance in this top-rated accommodation (currently 9.5 on Booking!).

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2-Bedroom House in Camacha

Location: Camacha

This traditional house in Madeira has such a cute garden that will give you that wonderful holiday feeling. The BBQ and the wood-fired hearth will create a cozy feeling no matter the time of year.

Calheta Beach House has an incredibly convenient location. It’s just a 20-minute drive inland from Funchal — well away from the city to have a tranquil stay, but close enough to easily do your sightseeing and dining in the capital. Not only that, but it’s just a 20-minute drive from the airport. Camacha is a great village to be based if you enjoy hiking; a whopping five different levada hikes (following ancient mountain water canals) have their trailheads in or near Camacha.

This holiday home is perfect for a family, having a spare room with two small beds and/or a crib, which is great for kids. (When we travel in Madeira with our toddler, being able to leave our travel crib at home is what usually seals the deal for us!)

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Quinta Dev贸nia

Location: Monte (near Funchal)

We are in LOVE with these three homes which are gorgeously overgrown with vines and plants. Surrounded by a lush garden filled with flowers, you will be hard-pressed to find a cuter B&B in Madeira than this.

Stumbling upon this gem while researching for this article, we now have it personally bookmarked for our next stay. We did see some reviews complaining about dogs barking in the neighborhood; this is quite common in rural Portugal, but could come as a surprise if you’re used to the cities.

The two houses and cottage (each rented separately) are located just a 20-minute drive outside of Funchal. You’ll be close to the botanical gardens in Monte, as well as several great viewing points and trails.

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Casa Boho Rooftop Suite

Location: Calheta

Situated along the coast and between the vineyards in Calheta, this stylish and soulful set of three apartments is truly a gem! Built and renovated by a German couple who fell in love with Madeira during a pandemic-induced escape to the island, they turned a rural property in need of some love into a modern boho chic B&B.

We especially recommend staying in Calheta if you’ll enjoy the nature surroundings away from the capital. You’ll be based on the sunny side of the island, but in the somewhat more remote western side. You’ll be walking distance from several fun local bars, and just a short drive away from Calheta Beach (one of the few sandy beaches in Madeira).

You have a choice between a rooftop suite, an apartment, and a ground-floor studio.

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Madeira Surf Lodge

Location: S茫o Vicente

This 18th-century country house is home to 5 different guest rooms, having been turned into a small guesthouse/hotel. The gorgeous garden is the perfect place to relax, while the shared kitchen facilities will let you self-cater during your stay.

Many guests praise Madeira Surf Lodge for its homely feel as well as the surfer vibes, which you can enjoy even if you don’t surf. If you’ve always wanted to give surfing a try, the hosts can arrange surfing lessons at the nearby beach.

S茫o Vicente is one of our favourite villages to stay in Madeira. It’s centrally located on the underrated green side of the island — perfect for surfing, road trips, hiking, or visiting the natural pools in Porto Moniz. Thanks to being near Madeira’s central tunnel, Funchal is still only 30 minutes driving away.

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Casas de Levada

Location: Ponta do Pargo

Located in the extreme west of Madeira, these stone cottages feature a wonderfully detailed garden and a tasteful interior design that just oozes charm and coziness.

This is the perfect place to relax near lots of nature and close to the coast. You can eat the fruits from the garden (such as bananas and oranges) and there is a small hobbit-esque bar where you can buy local products. Fresh bread is brought to your cottage every morning.

Guests praise the WiFi speeds, the breakfast, and the host’s friendly cats!

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