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We selected the 48 homes worth renting in this location

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Home spotlights in Monastiri

The Way of Bliss

The Way of Bliss

  • 2 guests

  • 1 bedrooms

Monastiri, Oia

Oia might be the most–loved location on Santorini, but you can still carve out your own space to experience this idyllic setting. And this beautiful apartment, nestled into the rocks, makes it possible to bask in expansive views whilst enjoying the close proximity to the town.

Golden Shades

Golden Shades

  • 4 guests

  • 2 bedrooms

Santorini, Greece

Experience the ultimate in relaxation at this hideaway on the east coast of Santorini. Just minutes from Oia, this is a place where serenity and sea views take centre stage – which, by the way, you can choose to enjoy from the sun-drenched terrace or private pool.

Cave In

Cave In

  • 2 guests

  • 1 bedrooms

Monastiri, Oia

With a sunroof terrace, a hot tub and spectacular views of the Aegean Sea, the caldera and the volcano, this traditional cave-style villa is perfect for a romantic couple or a solo traveller looking to explore the island. Combining original features with modern decor to create a stylish living space – from the whitewashed walls and dome ceiling to the hemp furnishings, wicker chair and neutral colour palette – it's a small yet mighty villa with heaps of character.

Caldera Bliss

Caldera Bliss

  • 6 guests

  • 3 bedrooms

Monastiri, Oia

The Caldera Bliss villa is a stunning and unique haven located in Oia, Santorini. Perched atop the ancient castle, it offers an extraordinary view of the caldera landscape.


We selected the top 3% holiday homes in Monastiri Family Friendly Rentals

Explore the 48 most perfect homes in our collection

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Most popular homes in Monastiri

Dormant Dreams

Dormant Dreams

  • 6 guests

  • 3 bedrooms

Monastiri, Oia

Whispering Moon

Whispering Moon

  • 2 guests

  • 1 bedrooms

Monastiri, Oia

Azure Perch

Azure Perch

  • 3 guests

  • 1 bedrooms

Perivolas, Oia

The Beautiful Blue

The Beautiful Blue

  • 4 guests

  • 2 bedrooms

Monastiri, Oia

Drifting Through Dreams

Drifting Through Dreams

  • 2 guests

  • 1 bedrooms

Monastiri, Oia

Charming Caldera Retreat

Charming Caldera Retreat

  • 2 guests

  • 1 bedrooms

Monastiri, Oia

Moonstone Isle

Moonstone Isle

  • 2 guests

  • 1 bedrooms

Perivolas, Oia

Don't It Make My Brown Eyes Blue

Don't It Make My Brown Eyes Blue

  • 6 guests

  • 3 bedrooms

Monastiri, Oia

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Discover the ultimate collection of luxury Family Friendly Rentals in Monastiri, Oia, Santorini, Greece. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Monastiri Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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