Book Luxury Holiday Rentals in Santorini

Award-winning homes from £98

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Home spotlights in Santorini

The Grape-Stomper

The Grape-Stomper

  • 16 guests

  • 8 bedrooms

Pyrgos Kallistis, Santorini

Situated underneath the Venetian-era Pyrgos Castle in Santorini, it's hard to imagine this beautiful setting being the site of a factory, but rather remarkably, this home has an industrial history. In a former life, the building was used solely for the production of wine and tsipouro.

Whisper Of The Sea

Whisper Of The Sea

  • 16 guests

  • 8 bedrooms

Imerovigli, Santorini

This haven of elegance and luxury is one of the biggest private villas on Santorini. Along the walking trail between Oia and Fira, this home sits in Imerovigli – a village of white buildings with blue domes cascading down the hillside.

Chalk White & Sage Green

Chalk White & Sage Green

  • 6 guests

  • 3 bedrooms

Akrotiri, Santorini

Once a winery, now a sanctuary for a small family or group of friends, this whitewashed villa is all about relaxing in style. Inside, it’s contemporary and minimalist – we loved the uncluttered spaces, double-height ceilings in the living area, wood accents and hand-selected, Scandi-style furnishings.

Myriad of Stars

Myriad of Stars

  • 4 guests

  • 2 bedrooms

Santorini, Greece

Boasting breathtaking views of the eastern Aegean Sea, with the islands of Naxos, Amorgos and Anafi visible from the comfort of your own bed, this villa offers the very best of Santorini. Located in the village of Imerovigli, you’ll have an array of sleek bars, fine-dining restaurants and sunset viewing spots within close proximity, but if nature’s more your thing, check out the Ekklisia Theoskepasti hiking trail that leads past the ruined, 13th-century Skaros Venetian Fortress.


We selected the top 3% holiday homes in Santorini Holiday Rentals

Explore the 170 most perfect homes in our collection

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Most popular homes in Santorini

A Greek Wonder

A Greek Wonder

  • 6 guests

  • 3 bedrooms

Santorini, Greece

Kiln & Stone

Kiln & Stone

  • 6 guests

  • 3 bedrooms

Santorini, Greece

Cycladic Blue

Cycladic Blue

  • 6 guests

  • 3 bedrooms

Santorini, Greece

On The Water's Edge

On The Water's Edge

  • 10 guests

  • 4 bedrooms

Akrotiri, Santorini

Wake Me Up

Wake Me Up

  • 5 guests

  • 3 bedrooms

Vothonas, Santorini

Soothe My Soul

Soothe My Soul

  • 4 guests

  • 2 bedrooms

Santorini, Greece

Sunset Suite

Sunset Suite

  • 2 guests

  • 1 bedrooms

Santorini, Greece

Cave Chic

Cave Chic

  • 10 guests

  • 5 bedrooms

Imerovigli, Santorini

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Santorini, Greece. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Santorini, Greece has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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