Book Luxury Short Stay Rentals in Astypalea

We selected the 468 homes worth renting in this location

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Home spotlights in Astypalea

Low Down Rolling Stone

Low Down Rolling Stone

  • 10 guests

  • 5 bedrooms

Santorini, Greece

A little off Santorini's well-trodden tourist trail, close to the authentic village of Pyrgos, this unique villa is guaranteed to appeal to lovers of subtractive design. The monolithic structure stands sentry over the surrounding countryside, dotted with vineyards that slope towards the Aegean Sea and offering views over Akrotiri Caldera and Aspronisi island.

A Bit of Blue Skies

A Bit of Blue Skies

  • 7 guests

  • 3 bedrooms

Monastiri, Oia

The views over the caldera from this cave home’s terrace in Oia are stunning. There are not one, but two Jacuzzis to relax in, one indoors and one outdoors with incredible vistas, while inside, the décor is classic and charming.

A View of the Castle

A View of the Castle

  • 4 guests

  • 2 bedrooms

Livadia, Kalymnos

Found in Astypalaia, where history and heritage collide, this home pays homage to both. Minimalist with a whitewashed Cycladic exterior, the interior is matched to create a coastal atmosphere whilst holding to tradition.

Hazy Horizons

Hazy Horizons

  • 6 guests

  • 2 bedrooms

Astypalea, Kalymnos

Soak up stunning views of the Aegean from this gorgeous Grecian villa, based in the heart of Astypalea and close to the old windmills that this region is famed for. We love this home's traditional design, with grand archways and built-in furniture.

We selected the top 3% holiday homes in Astypalea Short Stay Rentals

Explore the 468 most perfect homes in our collection

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Most popular homes in Astypalea

Angel of the Sky

Angel of the Sky

  • 4 guests

  • 1 bedrooms

Monastiri, Oia

Aegean White

Aegean White

  • 6 guests

  • 3 bedrooms

Perivolas, Oia

Thera Winds Blowing

Thera Winds Blowing

  • 4 guests

  • 2 bedrooms

Vourvoulos, Santorini

On The Water's Edge

On The Water's Edge

  • 10 guests

  • 4 bedrooms

Akrotiri, Santorini

Moonstone & Olive

Moonstone & Olive

  • 6 guests

  • 2 bedrooms

Monastiri, Oia

Azure Flecks

Azure Flecks

  • 4 guests

  • 2 bedrooms

Livadia, Kalymnos

Sanctuary of Solitude

Sanctuary of Solitude

  • 6 guests

  • 3 bedrooms

Monastiri, Oia

The Horizon's Cradle

The Horizon's Cradle

  • 8 guests

  • 3 bedrooms

Monastiri, Oia

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in Astypalea, Kalymnos, Greece. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Astypalea luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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