Book Luxury Vacation Rentals in Astypalea

Award-winning homes from £98

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Home spotlights

Crystal Vistas & Castle Views

Crystal Vistas & Castle Views

  • 4 guests

  • 2 bedrooms

Astypalea, Kalymnos

An island washed in the colours of the Grecian flag, Astypalea is a quiet holiday destination that’s ideal for a peaceful break – and you’ll be perfectly placed for exploring all of it from this stunning villa. This home truly has it all – dreamy interiors, luxurious amenities, and an absolutely breathtaking view of Astypalea Castle – we reckon it’s one of the best on the island.

Honey & Thyme

Honey & Thyme

  • 4 guests

  • 2 bedrooms

Astypalea, Kalymnos

This whitewashed hideaway sets the tone for a laid-back stay on the dreamy island of Astypalea. Featuring two jacuzzi pools alongside mesmerising Aegean views and soothing interiors, every detail evokes the magic of island living.

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.

Adonis Blue

Adonis Blue

  • 2 guests

  • 1 bedrooms

Astypalea, Kalymnos

Appearing like a wedding cake out of the verdant hills of Astypalaia, this palatial whitewashed structure has been converted into three design-led villas, and here is one of them. The interiors are enviably chic: smooth concrete floors, exposed stonework walls, and a grey-blue colour palette create the architectural ambiance, while statement lampshades, an indoor bamboo plant in the high-spec kitchen, and artful wall hangings provide idiosyncratic charm.


We selected the top 3% holiday homes in Astypalea Vacation Rentals

Explore the 8 most perfect homes in our collection

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Most popular homes

The Phoenician Princess

The Phoenician Princess

  • 2 guests

  • 1 bedrooms

Astypalea, Kalymnos

Crystal Chimes

Crystal Chimes

  • 4 guests

  • 2 bedrooms

Astypalea, Kalymnos

Sanctuary Of Stone

Sanctuary Of Stone

  • 6 guests

  • 3 bedrooms

Astypalea, Kalymnos

Olive Opal

Olive Opal

  • 4 guests

  • 2 bedrooms

Astypalea, Kalymnos

Cerulean View

Cerulean View

  • 8 guests

  • 4 bedrooms

Kalymnos, Greece

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Astypalea, Kalymnos, Greece. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Astypalea Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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