We all know the Santorini stereotype: a honeymoon paradise where love-struck couples dine cliffside as they watch the sunset over the romantic caldera. It’s true—and the island’s caldera is a must-see view, whoever you’re with—but you’ve probably heard the downsides to this Greek hotspot too: crowds you can’t escape, and cookie-cutter accommodation options that come at a premium. For those in the know, there’s a different way to do it, thanks to a whole host of lovingly restored and renovated private homes that offer you your own slice of this idyllic destination.

The Best Airbnbs in Santorini, According to Vogue

• For honeymooning couples: Arota Villas, from $2,164 per night
• For a central location: Terracotta Cave House 2, from $594 per night
• For bohemian charm: Hiraeth, from $757 per night
• For the caldera without the crowds: Akrorama Villa, from $1,541 per night
• For a traditional cave house: Cave Kanava Winery Villa, from $424 per night
• For a group getaway: Le Blanc Resort, from $1,121 per night

Coveted-but-crowded Oia is a convenient place to stay—if you seek out clever accommodation choices that go beyond the obvious and swerve the masses, that is. But venture beyond the attractions of Oia, Fira, and Imerovigli, and you might be surprised at the breadth of history, tradition, and—believe it or not—space available.

These Santorini Airbnbs span the island’s full terrain, from bustling hotspots to sleepy villages and rolling vineyards to ancient ruins. (Some of them even come with the oh-so-sought-after caldera view.) Included in our edit are 200-year-old cave houses, private villas perched atop the highest hills, and Cycladic homes with sun-dappled terraces. Without further ado, read on to bookmark our favorite vacation rentals on the island—because there’s a whole lot more to this Greek locale if you’re curious enough to seek it out.

Terracotta Cave House 2

A splash of color in a sea of whitewashed homes, three-floored Terracotta Cave House stands out among its Oia neighbors in all the right ways. Overlooking the coveted caldera, mornings are probably best spent on the ground-floor terrace for two, or soaking up the Santorini sun from its rooftop (which has panoramic views over postcard-pretty Oia and its tumbling cliffs). Dozing off on the second floor mezzanine and waking to quiet mornings just steps away from Santorini’s most in-demand village has all the makings of a memorable holiday.

Rooms: 1 bedroom, 1 bathroom

Amenities: Caldera view, private rooftop terrace, balcony, kitchenette, AC, on-street parking

Location: Oia

Cycladic Suite

With a spacious terrace, you’d be forgiven for wanting to forgo Imerovigli’s cliffside restaurants in favor of watching the sun set over the caldera from your own private retreat. (The hot tub is also a strong contender for best views.) With its earthy, off-white interiors, cave-like arches, and rustic decorative touches, you might find it difficult to tear yourself away from this two-bedroom during the day, too.

Rooms: 2 bedrooms, 1 bathroom

Amenities: Caldera view, outdoor dining, AC, hot tub

Location: Imerovigli

Cave Kanava Winery Villa

Carved into a cliff, this 200-year-old former winery was remodeled into a stylish one-bedroom apartment in 2023. Its traditional features marry seamlessly with modern design: curved lines, textured taupe walls, and layered lighting inside; a rooftop Jacuzzi and sunbeds outside; original wine-making tools in the basement for the curious hobbyist. Ideal for solo travelers, couples, or cocooning honeymooners, this cozy spot away from the crowds is less than a 10-minute drive to the island’s caldera.

Rooms: 1 bedroom, 1 bathroom

Amenities: Heated Jacuzzi, kitchen, outdoor dining, wine cellar, AC, on-street parking

Location: Mesaria

Master Villa, Santorini Sky

Set on Santorini’s highest hill, far away from even the thought of a crowd, Santorini Sky is a multi-suite property especially popular with honeymooners; though my short solo stay was an utterly restorative break from everything (and everyone), too. All the suites are spacious, but the Master Villa—with a private terrace, indoor and outdoor showers, an infinity pool, a double daybed, and a Jacuzzi—is the best of them all.

The only time I encountered other guests was during breakfast at the communal lounge, where plentiful light bites are available all day—and where I was encouraged to fill a basket with to-go snacks. Otherwise, it was just me, my infinity pool, and a bird’s-eye view of the island’s entire south coast for the majority of my stay. And if, like me, you can’t drag yourself away for dinner, on-site staff make it easy to order in from local restaurants.

Rooms: 1 bedroom, 1.5 bathrooms

Amenities: Island and sea view, infinity pool, Jacuzzi, outdoor dining area, paid washer, AC, kitchen, Marshall sound system, security cameras

Location: Pyrgos Kallistis

Canava Villa 1

It’s just three steps from bed to bathtub in this former winery-turned-cave house, where everything is carved into the mountain rock. Intimate and endlessly charming, this two-bedroom villa is perfect for small groups or families with children who can make use of the secondary twin room. Located in medieval Emporeio, days here move slowly; perhaps you’ll begin with breakfast on the terrace, followed by a cooling dip in the outdoor pool. Of course, evenings are spent watching the sun set over the sea from the rooftop.

Rooms: 2 bedrooms, 2 bathrooms

Amenities: Valley view, swimming pool, outdoor dining area, washer, AC, kitchen

Location: Emporeio

Arota Villas

This villa is the perfect place for groups of four who want a remote stay with a full slate of amenities. It offers a secluded location in Santorini’s quieter south, plus a heated infinity pool with caldera views, a Turkish-style steam room, chef-prepared breakfasts—which you can take on the outdoor terrace or snuggled up in bed—and two in-room Jacuzzis. The style merges modern minimalism with Cycladic design—but with stand-out features like geometric cutouts and unexpected sculptures for a little bit of playfulness.

Rooms: 2 bedrooms, 3 bathrooms

Amenities: Caldera view, heated infinity pool, two Jacuzzis, steam room, kitchen, breakfast, in-villa dining menu, outdoor dining area, AC, on-site parking

Location: Akrotiri

Hiraeth

This is not your typical Cycladic Airbnb. Bursting with character, color (those green floors!), artwork, and plants, this home in a small, traditional Santorinian village is like no other on the island. It’s hard to pick just one star of the show in this eclectic space; though the lush outdoor oasis, that includes a pool surrounded by cacti and palm trees, might just cinch it. The pool actually connects two homes (which you can rent independently or together), and there’s a shared entrance area where treats like homemade jams and fresh sourdough are laid out daily for guests.

Rooms: 1 bedroom, 1 bathroom

Amenities: Shared outdoor pool, outdoor dining area, AC, on-street parking

Location: Megalochori

Akrorama Villa

We’ve compiled a lot of options, but this might just be Santorini’s prime caldera-viewing spot. Located on the outskirts of ancient Akrotiri, you’ll struggle to pull yourself away from the plush poolside daybeds; you get sea, vineyard, and volcanic landscape views all at once here. With four bedrooms, this is an ideal space for a group getaway. The aesthete in particular will appreciate the Mediterranean-meets-Japandi minimalist design, complete with cave-like interiors, blue shuttered windows, and archway-lined outdoor dining.

Rooms: 4 bedrooms, 4 bathrooms

Amenities: Sea and vineyard view, AC, kitchen, outdoor dining area, grill, washer, on-site parking

Location: Akrotiri

Le Blanc Resort Santorini

Light, bright, spacious, and airy, these side-by-side villas (Le Blanc Suite and Le Blanc Nest) are ideal for big groups—put together, you can sleep up to 12 guests. While available to rent individually, these villas are best rented as a pair, giving everyone in your group access to the small dipping pool on Le Blanc Nest’s veranda as well as group-friendly amenities like communal outdoor dining areas, en-suite bathrooms, and plenty of parking. Inside, modern, minimalist design by Greek architect Ioanna Tsagkouli sees sleek white walls softened by rattan rugs, chunky woven ottomans, and natural wooden finishes.

Rooms: 6 bedrooms, 5.5 bathrooms

Amenities: Sea view, hot tub, swimming pool, outdoor dining area, washer, AC, kitchen, on-site parking

Location: Mesaria