Book Luxury Winter Rentals in Santa Cruz

We selected the 474 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Santa Cruz

Roses on the Balcony

Roses on the Balcony

  • 6 guests

  • 2 bedrooms

Machico, Madeira

A ten-minute walk to the beach and two minutes on foot to shops, restaurants and bars, this apartment is in the buzzing coastal town of Machico. There’s plenty to keep you entertained here, but if you’re craving a big place to hang out, the city of Funchal is just a twenty-minute drive away.

On the Reef

On the Reef

  • 6 guests

  • 2 bedrooms

Santa Cruz, Madeira

Just a short stroll from Palmeiras beach, this apartment is ideal for a family getaway. Sure, its convenient location means you’re surrounded by neighbouring homes so it lacks a little privacy, but we think the easy access to restaurants, shops and the coast makes up for it.

Vintage Madeira

Vintage Madeira

  • 3 guests

  • 1 bedrooms

Machico, Madeira

Situated in the centre of Machico, just a short stroll from the beach, this apartment offers a comfy nest for a couple or a small family visiting Madeira and looking for a relaxing stay. The place emanates a vintage aesthetic – from the opulent furnishings to the wooden floors and large windows, the interior is certainly more bygone elegance than modern minimalist.

The Edge of Time

The Edge of Time

  • 2 guests

  • 1 bedrooms

Caniço, Santa Cruz

Set a five-minute drive from the basalt stones of Reis Magos Beach, this homely apartment is the perfect base for short sojourns and longer stays on Madeira’s south coast. Inside, soothing neutral tones take precedence – expect whitewashed walls, polished wood floors and greige textiles.


We selected the top 3% holiday homes in Santa Cruz Vacation Rentals for Winter

Explore the 474 most perfect homes in our collection

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Most popular homes in Santa Cruz

Amber & Azure

Amber & Azure

  • 6 guests

  • 3 bedrooms

Gaula, Santa Cruz

Ready for Takeoff

Ready for Takeoff

  • 5 guests

  • 2 bedrooms

Gaula, Madeira

Cheers to the Ocean

Cheers to the Ocean

  • 4 guests

  • 2 bedrooms

Gaula, Santa Cruz

By the Crystalline Ocean

By the Crystalline Ocean

  • 12 guests

  • 6 bedrooms

Sao Goncalo, Madeira

Toast of the Coast

Toast of the Coast

  • 6 guests

  • 3 bedrooms

Caniço, Santa Cruz

Beyond the Bougainvillea

Beyond the Bougainvillea

  • 2 guests

  • 1 bedrooms

Funchal (Santa Maria Maior), Funchal

Glistening Blue

Glistening Blue

  • 2 guests

  • 1 bedrooms

Funchal (Santa Maria Maior), Funchal

Magical Madeiran Dream

Magical Madeiran Dream

  • 2 guests

  • 1 bedrooms

Sao Goncalo, Madeira

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Check upcoming rates & availability for Santa Cruz Vacation Rentals for Winter


Frequently asked questions

Browse our remarkable collection of luxury Vacation Rentals for Winter in Santa Cruz, Madeira, Portugal. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Santa Cruz. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.

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