Book Luxury Villas in Estreito da Calheta

We selected the 114 homes worth renting in this location

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Home spotlights in Estreito da Calheta

Atlantic Bound

Atlantic Bound

  • 6 guests

  • 3 bedrooms

Raposeira Do Logarinho, Fajã da Ovelha

On a lush green hillside sits this stunning modern villa, with views down the cascading slope all the way to the Atlantic. A refurbished and extended old stone cottage, you'll find a luxurious space with huge floor-to-ceiling windows and sliding doors providing panoramic views.

Sun, Sea & Solitude

Sun, Sea & Solitude

  • 4 guests

  • 2 bedrooms

São Jorge, Santana

If you long for a quiet retreat in a quaint cottage by the sea, your search is over – this home will tick every one of your holiday boxes and more. Nestled in São Jorge on the northern coast of Madeira, this is seclusion at its finest.

Tinta Negra

Tinta Negra

  • 8 guests

  • 4 bedrooms

São Vicente, Madeira

Between the ancient trees of the Laurissilva Forest and the rolling fields of São Vicente, this home sits within a sprawling vineyard. Tinta Negra and Verdelho grapes grow plump in the sun, ready to be harvested for the island’s famous Madeira wine – you can experience this yourself if you time your visit right.

The Land's End

The Land's End

  • 4 guests

  • 2 bedrooms

Arco da Calheta, Madeira

Perched high above the ocean, facing west so the sun hits the terrace most hours of the day, this villa’s position is the envy of the island. Huge glass doors slide open to the wrap-around terrace where sun loungers make the most of the daily rays and a neat blue swimming pool waits for its surface to be disturbed during the heat of the day.


We selected the top 3% holiday homes in Estreito da Calheta Villas

Explore the 114 most perfect homes in our collection

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Most popular homes in Estreito da Calheta

Picture Perfect Horizon

Picture Perfect Horizon

  • 8 guests

  • 4 bedrooms

Estreito da Calheta, Madeira

Madeira Cake

Madeira Cake

  • 6 guests

  • 3 bedrooms

Arco da Calheta, Madeira

Cherry Wine

Cherry Wine

  • 8 guests

  • 3 bedrooms

Ponta do Pargo, Calheta

Drop of Light

Drop of Light

  • 9 guests

  • 4 bedrooms

Funchal (Santa Maria Maior), Funchal

Nature of the Valley

Nature of the Valley

  • 6 guests

  • 3 bedrooms

São Vicente, Madeira

Villa Azure

Villa Azure

  • 7 guests

  • 3 bedrooms

Arco da Calheta, Madeira

Blue Reflection

Blue Reflection

  • 6 guests

  • 3 bedrooms

Arco da Calheta, Madeira

Poncha in Paradise

Poncha in Paradise

  • 6 guests

  • 3 bedrooms

Arco da Calheta, Madeira

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Frequently asked questions

Secure a luxury stay in one of the remarkable Villas in our Estreito da Calheta, Madeira, Portugal collection. Our quality and consistency is unmatched, with only the top 3% of homes making it onto our site. Our meticulous home experts test everything from shower pressure to a home's feel and atmosphere, so there really is no need to worry about a thing. Your chosen home is also guaranteed to be fully furnished, with an excellently-equipped kitchen, essential bathroom toiletries, and linens all included. Acquire the help of our friendly experts, on standby 24/7 and always eager to assist you in your hunt for the finest luxury Villa in the entirety of Estreito da Calheta.

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