Summer has its own particular set of requirements for travel. You need a destination that’s sunny and warm, that goes without saying, with beautiful beaches or cliffside swim spots that provide a scenic way to cool off. You need someplace that knows how to eat, taking advantage of all the fresh produce that comes with the season. You need a slower, laid-back pace that encourages late starts and even later dinners, with time built into the local schedule for an afternoon siesta. You need, in other words, a trip to Greece.
From the whitewashed charm of the Cyclades to the lush green of the Sporades to the more colorful, Euro-influenced Eptanisa, each geographic group has its own distinct character. (There are over 200 inhabited isles in the country; you are spoilt for choice.) And while the bulk of foreign tourism empties out comes September 1st, the best time to visit is actually early fall—everything quiets down, but the warm weather continues through early October. Part of narrowing down your search involves picking out the right Greek island Airbnb for your ideal holiday.
Vogue’s Guide to the Best Greek Island Airbnbs:
- For Traditional Greek Design: Kambones 1615 Ηistoric Venetian Home, Naxos, from $416 per night
- For a Far-Flung Destination: Maison avec Jardin, Patmos, from $437 per night
- For a Stylish Studio: Guest House, Sifnos, from $162 per night
- For a Luxury Villa: White Dune Villa, Mykonos, from $555 per night
- For a Quick Trip from Athens: Touching the Sea Villa, Hydra, from $757 per night
- For Unbeatable Seaside Views: Thavma View, Milos, from $689 per night
- For a Group Trip Off the Beaten Path: Galazio, Ithaca, from $336 per night
- For a Rugged Spot Built into the Mountain: Faros Villa Guest House, Serifos, from $428 per night
Villa Petra, Andros
Despite being one of the first Cycladic islands reached from Athens, Andros remains low-key. This is mostly due to its makeup: It’s a rugged, mountainous island, with the population spread out among small, remote villages, and not yet overdeveloped. Lean into this off-the-beaten path charm with an Airbnb that also feels set away from the world. Follow a dirt path (and several sheep) to reach this stone villa, which can sleep up to four and seems to be completely surrounded by the Aegean.
Rooms: 2 bedrooms, 2 bathrooms
Amenities: Outdoor shower, washer/dryer, record player, crib available upon request, AC, indoor fireplace, patio, grill, outdoor dining, pet-friendly, pool
Location: Andros
Maison avec Jardin, Patmos
The mystical, far-flung island of Patmos is off the main path of first-time tourists making a beeline for Santorini’s blue domes; the return visitor (or anyone craving a quieter, less flashy holiday) will fall quickly in love. This villa, recently renovated and within walking distance of Chora, only expedites the obsession. Immaculately decorated, with stately furnishings and a restrained palette, it has all the charm of a boutique hotel. The outdoor area is scented by lavender and shaded by trees, and is equally beautiful.
Rooms: 2 bedrooms, 2 bathrooms
Amenities: Outdoor shower, washer, wood-burning fireplace, patio, outdoor dining
Location: Patmos
Casa Luminosa, Kefalonia
Kefalonia is huge—it’s the biggest island in the Eptanisa, and with so much to see you’ll need a car. Situate yourself in Assos, a small fishing village on the west coast; from the colorful pastel houses to the incredible sunset, you’ll find it a calming home base. This house captures the best of the town. Enjoy direct sea views from its various balconies and patios; you can even see the old Venetian castle. Inside, there’s lots of room for everyone in your group to spread out, including a full kitchen and workspace.
Rooms: 2 bedrooms, 2 bathrooms
Amenities: HDTV, AC, heating, patios/balconies, outdoor dining, luggage dropoff allowed
Location: Kefalonia
Townhouse with Sunrise Views, Skiathos
Located right in Chora, by the port your ferry will drop you off at, this townhouse offers a lot of space for its central location. You’ll be right in the middle of the bustling town, with its winding roads dotted with small boutiques and restaurants, and at the base of the church of Saint Nicholas; climb up to see the whole island. Its three floors include a rustic kitchen, a sunny bedroom with a terrace, and a cozy living room with an original fireplace.
Rooms: 1 bedroom, 2 bathrooms
Amenities: Washer, TV, crib, AC, wood-burning fireplace, pet-friendly
Location: Skiathos
Spilia Suite, Santorini
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
Chateau Gournia, Crete
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
Kambones 1615 Ηistoric Venetian Home, Naxos
This manor home dates back to 1615, and has been family-owned for centuries. It sits amongst olive groves and almond orchards, with lots of room outside to explore (the hosts hold classical guitar recitals in a nearby olive press—attendance is open to guests). The house has been preserved to highlight some of the more old-world aspects—spot wood beams, stone floors, and aqua window frames in nearly every room—for a taste of traditional Cycladic style. To make the most of your stay, be sure to rent a car; Naxos has beautiful beaches, and as the Airbnb is tucked away closer to the mid-land village of Kourounochori, you’ll need a vehicle to get around.
Rooms: 2 bedrooms, 2 bathrooms
Amenities: Bathtub, washer, piano, wood-burning fireplace, free parking, cleaning available
Location: Naxos
Villa Armonia, Paros
The port town of Piso Livadi is a well-connected and slightly more low-key alternative to the busier towns of Naousa and Parikia—for a group trip to Paros, consider a stay here. We won’t need to sell you much on the villa itself: Electric green shutters hide a sunny, sprawling home, with room for up to six people. There’s a swimming pool and an outdoor kitchen, for family dinners at home after long days on the beach, and lots of smaller cafés and convenience shops a quick walk away. You’ll also be well-situated for one of the most underrated reasons to visit Paros: leaving it. Day trips to the tiny Koufonissia islands (home to some of the clearest water in the Cyclades) are only possible via ferry at a handful of ports—Piso Livadi is one of them.
Rooms: 3 bedrooms, 3 bathrooms
Amenities: Washer, crib, AC, indoor fireplace, grill, shared pool, free parking
Location: Paros
Thavma View, Milos
Speaking of beaches—Milos is renowned for being home to some of the best in the Cyclades, with over 70 scattered around the island. This seaside rental is located in the old fisherman village of Fyropotamos, putting you directly on the turquoise water. The terrace, with its spacious dining table, is the clear centerpiece of the apartment; though inside, a commitment to minimalism creates a calming atmosphere.
Rooms: 1 bedroom, 1.5 bathrooms
Amenities: TV, AC, indoor fireplace, pet-friendly
Location: Milos
Touching the Sea Villa, Hydra
A five-minute water taxi from the port of Hydra sits this waterfront villa, with a far-reaching terrace that gives you unfettered views of the Aegean. (It goes without saying that sunsets here are incredible: Plan accordingly with a stop at the local market to pick up supplies for aperitivo at home before heading out for dinner—the property is walking distance to two tavernas.) Inside, you’ll find two bedrooms and a full kitchen, with large windows providing peeks of the surrounding sea from every part of the home.
Rooms: 2 bedrooms, 1 bathroom
Amenities: Outdoor shower, washer, TV, sound system, crib, air conditioning, fireplace, cleaning available
Location: Hydra
Kymo II, Spetses
The perfect outpost for a weekend trip from Athens, Spetses is another Argosaronic island with a quieter pace and a glamorous feel. This spot, around a 10-minute walk from the port, puts you right near all the restaurants and shops. There’s a little outdoor courtyard dotted with fruit trees and fuchsia bougainvillea, complete with a table for breakfast, but inside, the decor leans so minimalist it’s almost monastic—you’ll leave feeling rested, recharged, and pondering getting a sink skirt (yes, absolutely).
Rooms: 1 bedroom, 1 bathroom
Amenities: Washer, indoor fireplace, air conditioning, free parking
Location: Spetses
Guest House, Sifnos
It’s becoming a favorite of European visitors for a reason: Slightly more low-key than the rest of its Cycladic counterparts, with a long history of ceramic craft and incredible food scene, Sifnos deserves a spot on your island hit-list. This guesthouse puts you right where you should be: in Apollonia, one of the main villages in a central cluster that comprises the livelier part of the island (Kafeneio Drakakis and Cafe Mosaico are two dinners not to miss). The studio is small but well-appointed, with an equipped kitchen, spacious shower, and outdoor seating nook for catching the sunrise.
Rooms: 1 bedroom, 1 bathroom
Amenities: AC, free parking
Location: Sifnos
Faros Villa Guest House, Serifos
For true quiet in the Cyclades, head to Serifos. It’s on the rugged side and definitely smaller than many of its neighbors, with a hilltop chora that’s well-known as one of the region’s most charming. This picturesque hillside Airbnb near the coastal village of Megalo Livadi is a true gem. It’s surrounded by the sea (even the bathtub has a door that opens up to slivers of blue) and feels one with the landscape—in some cases, literally. The bed is built into one of the ancient stone walls that make up the base of the home.
Rooms: 1 bedroom, 2 bathrooms
Amenities: Bathtub, outdoor shower, washer/dryer, TV, sound system, crib, air conditioning, building staff
Location: Serifos
White Dune Villa, Mykonos
Under-the-radar gem for in-the-know travelers, Mykonos is not, but the island is more than black van transfers and aspiring DJs in midlife crisis: Located near Agios Sostis beach (home to the beloved Kiki’s Taverna and crystal blue waters), this Airbnb is so architecturally stunning it’s worth booking a visit to the island around. The pool sits on a sprawling terrace, overlooking the sea for maximum tranquility. Because it’s part of a villa group, you also get access to hotel-like amenities, including a maid service, concierge, and airport transfer—all the luxury of a resort, with the privacy of a vacation rental.
Rooms: 2 bedrooms, 2.5 bathrooms
Amenities: Washer, TV, crib and high chair, air conditioning, swimming pool, free parking
Location: Mykonos
Galazio, Ithaki
The Ionian island of Ithaki can only be reached via ferry from the western part of the mainland as well as islands like Kefalonia and Zakynthos; for that reason, it’s a great option for the traveler who wants quiet and calm out of their Greek holiday. I recently stayed in this gorgeous house with a couple of friends, and it was the perfect base for exploring the island—located on the outskirts of the main town of Vathy, we were just a short walk to coffee in the morning and dinner at night. The outdoor shower is only one highlight of the outdoor area, which is shrouded by orange trees and frequently visited by neighborhood cats. We elected to stay in and cook a big pasta dinner one night, following a long day on a rented motorboat; the terrace overlooking the surrounding buildings made for a setting just as memorable as any taverna.
Rooms: 2 bedrooms, 1 bathrooms
Amenities: Outdoor shower, air conditioning, free parking, housekeeping available during stay
Location: Ithaki/Ithaca
Bougainvillea’s Little Balcony, Syros
Tucked up in the hills of Ano Syros (the Venetian settlement of Syros that dates back to around 1200), this charming home is full of unique touches. From exposed stone walls to wood beams to an eclectic collection of vintage furnishings, it’s designed to enchant. I stayed here a couple summers ago with a friend; Every evening was spent on the tiny little balcony among the bougainvillea, playing rounds of gin rummy with glasses of rosé and listening to the music from the winding streets below well into the night. (For a quick dinner, there’s a bustling souvlatzidiko right around the corner where you can order takeaway; it’s inexpensive and delicious.)
Rooms: 1 bedroom, 1 bathroom
Amenities: Balcony, TV
Location: Syros
Pistachio House, Aegina
The closest island to Athens—the ferry trip can be as short as 30 minutes—is Aegina, a small but lively isle known for its pistachios. Fitting, then, that you should stay in a beautiful Airbnb situated directly in a pistachio field. It’s a little farther out from the main town, so you’ll need a car or scooter to get around, but once you’re here you’ll quickly see its appeal: The rental is carefully decorated with Mediterranean minimalism in mind. From the azure zellige tiles to the matching shutters to the whitewashed wood ceiling beams, it’s a stylish spot whose appeal is only heightened by the presence of a completely private little swimming pool.
Rooms: 2 bedrooms, 1 bathroom
Amenities: Washer, AC, pool
Location: Aegina
Sea Access & Sunset, Corfu
Corfu (or Kerkyra) is a large Ionian island with a unique makeup: A blend of Venetian, French, and even British influences makes for an architectural landscape unlike most other islands in the country. Rent a car and head to Afionas, a northwestern village of colorful houses and sunset views of Arillas Bay. It’s where you’ll find this home, which is actually made up of two apartments (rent them together, if you’re traveling with a large group) and faces directly out onto the sea. Rustic wood beams and stone walls create a cozy environment, and the extra-large kitchen is great if you prefer to take advantage of local produce and cook some meals at home.
Rooms: 2 bedroom, 1.5 bathroom
Amenities: Washer, TV, air conditioning, indoor fireplace, grill, free parking
Location: Corfu
