First-timers to the Greek isles will likely want to make a pit stop in Santorini; but while an evening in Fira or Oia to catch the sunset is an unavoidable part of any itinerary, you’ll want to book your lodging in a quieter, less-touristy part of the croissant-shaped island. Akrotiri, a Bronze Age settlement in southern Santorini, is built into the craggy cliffs and offers incredible views (plus, the famous red sand beach is here, just a 10-minute drive from this Airbnb). The home feels completely secluded, high above it all with a private, heated pool. Breakfast is delivered to the suite daily; choose to dine on the shaded patio or one of the reclining lounge chairs in the sun.
Rooms: 1 bedroom, 1 bathroom
Amenities: Outdoor shower, TV, air conditioning, loungers, pool, breakfast, housekeeping available
Location: Santorini
Courtesy of the Airbnb photography community
Greece’s largest island needs at least a couple of weeks to properly explore—and even then, you’ll have only scratched the surface. If you have the time for a longer stay (and a car), go here, and book a villa to house your entire group. On the eastern side of the island, past the town of Agios Nikolaos, this rosy pink home sits perched on the Mirabello Gulf and offers complete privacy. Designed by an architect, it’s full of unique features—from a custom coffee table built out of an old millstone to the mint green door trimmings. Outdoors, there’s lots of room for activities, from the bocce court to the covered courtyard that houses a pizza oven.
Rooms: 4 bedrooms, 2 bathrooms
Amenities: Bathtub, washer, Bluetooth sound system, crib and high chair available upon request, board games, air conditioning, indoor fireplace, sun loungers, pet-friendly, cleaning available
Location: Crete
Courtesy of the Airbnb photography community
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