Book Luxury Monthly Rentals in Oia

We selected the 58 homes worth renting in this location

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Home spotlights in Oia

Sweet Peony

Sweet Peony

  • 2 guests

  • 1 bedrooms

Monastiri, Oia

200 years ago, this windmill produced bread for the whole of Santorini. Today, it’s a dreamy retreat just for two.

The Captain's Villa

The Captain's Villa

  • 8 guests

  • 4 bedrooms

Monastiri, Oia

An old sea captain’s house, this mansion of a villa sits in the postcard-perfect town of Oia. This is perhaps Santorini’s most photogenic town, where the classic blue-domed buildings cascade down the hillside towards the sea.

Storybook Ending

Storybook Ending

  • 8 guests

  • 3 bedrooms

Perivolas, Oia

We defy you not to be impressed by this beautifully-appointed villa overlooking the deep blues of the Aegean and the picturesque village of Oia, just 500m from your doorstep. Kitted out with several terraces and a bubbling jacuzzi plunge pool, when it comes to relaxation and tranquility, you couldn't wish for a more idyllic set up.

Azure Perch

Azure Perch

  • 3 guests

  • 1 bedrooms

Perivolas, Oia

Nestled among the craggy cliffs of Santorini, this cosy nook offers a peaceful respite from the hustle and bustle of everyday life. Ideal for romantic retreats and solo getaways alike, the cave-like home boasts sweeping views of the Aegean Sea and a private tucked-away hot tub – all with the benefit of having the island's main town, Oia, on its doorstep.


We selected the top 3% holiday homes in Oia Monthly Rentals

Explore the 58 most perfect homes in our collection

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Most popular homes in Oia

Santorini Serenity

Santorini Serenity

  • 10 guests

  • 5 bedrooms

Monastiri, Oia

Aegean Haven

Aegean Haven

  • 2 guests

  • 1 bedrooms

Monastiri, Oia

Mill in the Sky

Mill in the Sky

  • 4 guests

  • 2 bedrooms

Perivolas, Oia

Let's Chill in the Cave

Let's Chill in the Cave

  • 7 guests

  • 3 bedrooms

Perivolas, Oia

Power of the Earth

Power of the Earth

  • 6 guests

  • 3 bedrooms

Monastiri, Oia

Moonstone Isle

Moonstone Isle

  • 2 guests

  • 1 bedrooms

Perivolas, Oia

Aegean White

Aegean White

  • 6 guests

  • 3 bedrooms

Perivolas, Oia

Moonstone & Olive

Moonstone & Olive

  • 6 guests

  • 2 bedrooms

Monastiri, Oia

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Oia, Santorini, Greece, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Oia Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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