Mediterranean cruises and island-hopping land tours are popular ways to see the Greek Islands, but, if you settle in for a few days in one place, you can really immerse yourself in local culture. These Airbnb rentals promise classic island accommodations, plenty of room to spread out, and some spectacular sunset views.
Accommodations fill up fast in Santorini — especially in the summer — so plan ahead and book this two-bedroom cliffside cave house in Oia. Antique furniture and beds built into the walls are beguiling, but the real showstopper here is the patio perched above the village, perfect for toasting the sunset with a glass of wine.
Santorini Must-Do: Pick up a paperback for the flight home at Atlantis Books, a cozy, subterranean bookstore in Oia run by two European and American expats.
Overlooking Mykonos Town, this three-bedroom villa‘s sleek white exterior gives way to uber-modern, minimalist furnishings inside, from the Eames-style chairs in the dining room to simple stone basin sinks in the bathrooms. Out back, you’ll find an extra-long infinity pool made for floating the day away.
Mykonos Must-Do: Head into Mykonos Town for dinner at To Maereio, a classic and popular Greek taverna. Tip: Order the meatballs, a secret family recipe.
Narrow streets, inviting town squares, and traditional stone homes define Crete’s villages. This one-bedroom 1930s charmer in coastal Malia is a superb example of the island’s architecture, nestled on a corner lot with its own private courtyard and balcony.
Crete Must-Do: The Venetians ruled Crete for more than 400 years, and their influence is evident in the island’s unique cuisine. Taste Cretan flavor on heaping plates of dakos (it’s like bruschetta) and kaltsounia (cheese pie) at Taverna Grameno in Palaiochora.
Unpack in one of the four bedrooms at Villa Kandili, which sits on a lushly landscaped cliff above Kanapitsa Bay. You could spend all day lounging on the terrace, watching sailboats pass in the distance, but when it’s time for a change of scenery, head down to the beach. It’s a three-minute walk away, and you’ll likely have it all to yourself.
Skiathos Must-Do: Follow the crowds to Koukounaries Beach, one of Greece’s most popular stretches of sand, for some prime people watching.
Greece’s second-largest island (also known as Evia) deals more in nature and ancient ruins than it does in over-the-top beach clubs. Bring the whole crew to Delenia, a beachfront compound with five bedrooms, two kitchens, a pair of living rooms, a pool, and more. After a round of tennis or a session in the Turkish hammam, everyone can gather under the pergola for dinner — the onsite staff prepares one meal a day.
Euboea Must-Do: Hike to the waterfalls at Drimonas, outside the village of Rovies. The easy, hour-long trek leads to a picturesque emerald-hued swimming hole.
Arrive at this quaint, one-bedroom house and head straight to the rooftop terrace, where views of the harbor and the distant Peloponnese are well worth your reservation alone. Later, the cafes and clubs in Hydra’s main village are a five-minute walk away.
Hydra Must-Do: Get a proper lesson in the island’s history at the Lazaros Koundouriotis Historical Mansion. The heirloom-filled, 18th-century estate is the former home of Koundourioitis, a ship maker who played a key role in the Greek War of Independence.
Villa Orion is a perfect example of the iconic architecture that puts Mykonos at the top of many travelers’ bucket lists: simple, whitewashed structures with bright blue shutters, overlooking the sea. There’s room to spread out in this five-bedroom space, located outside of Mykonos Town in the quiet, residential area of Cavo Delos. A main house and two smaller guesthouses surround a stunning pool area with an open-air bar and BBQ.
Mykonos Must-Do: Watch the sunset at Little Venice on the island’s west coast, while sipping a daiquiri at Caprice. (Be sure to make a reservation in advance.)
Choose from one of nine villas tucked amongst bright gardens and overlooking the Aegean Sea at Agia Irini Villas. The simple, Cycladic-style accommodations have private balconies and terraces, living rooms and kitchens, and access to a secluded beach that’s reached via a short footpath through the gardens.
Paros Must-Do: Feast on fresh octopus, grilled squid, and fried calamari at Captain Pipinos, an old-school waterfront taverna in the village of St. Giorgio Antiparos.
Make dinner together in the country-style kitchen of this three-bedroom house — a converted school building that’s been in the same family for generations. The furniture inside skews more grand and antique than polished and austere, while the courtyard dining area and the wooden sauna are extra perks you’ll appreciate.
Corfu Must-Do: Wander through the cobblestoned streets of Old Town — a 15-minute walk from your rental — popping in and out of tiny souvenir shops. Pick up a bottle or two of locally made olive oil to bring home.
Suite No. 7, a private studio in the larger Anita’s Villa complex, sits near the top of Santorini’s caldera in Imerovigli, which means the views from your balcony are pretty impressive. Other dreamy features include soaring arched ceilings and access to a spacious rooftop terrace that’s shared by all eight units in the compound.
Santorini Must-Do: For a different perspective, take in Santorini’s beauty from the sea on a sunset catamaran cruise. Brothers Markos and Chris — the owners of Anita’s Villa — can handle the arrangements, and they’re happy to share their island pro tips.