Santorini vacation rentals are about as iconic as the island’s caldera, sunset lookouts, and volcanic black beaches. Cycladic-style properties in the vibrant capital Fira (Thira) and chic Oia are carved into the volcanic ash and partially underground to protect from the tempestuous climate. Scattered in quieter villages across the Greek isle, you’ll find luxurious Santorini villa rentals with pools. Read on for the most unique Airbnbs in Santorini, Greece, across cave houses and private estates.
Photo: Airbnb
20 Airbnbs in Santorini With Epic Sea Views and Pools
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We hope you love the Airbnb Santorini vacation rentals we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
- Top-rated all-inclusive and luxury Airbnbs in Santorini
- Airbnbs in Fira (Thira), Santorini
- Airbnbs in Oia, Santorini
- Airbnbs in Perissa, Santorini
- Airbnbs in Kamari Beach, Santorini
- Airbnbs in Firostefani, Santorini
Top-rated all-inclusive and luxury Airbnbs in Santorini
Luxury Santorini Airbnb with private pool
Set within 2.5 acres of an estate, this stone-clad retreat consists of a main house plus a self-contained unit wrapped around a pair of restored kilns. Interiors feature crisp white walls punctuated with cobalt upholstery and tangerine kitchenware. Out on the deck, the pool, heated spa tub, and dining zone overlook the Aegean. Renting this all-inclusive Santorini villa covers your airport transfers, daily breakfast, and housekeeping; they even throw in a hire car on the house.
Ten guests, five bedrooms
Price: $969 per night
Santorini Sky – boutique bolthole with private pool
Soaring 2,000 feet over the island in a terraced valley, Santorini Sky is a swanky hideaway near Pyrgos, far from the coastal hotspots. Carved out of the mountainside, the Retreat Suite is the newest addition to this trending Airbnb resort with a private heated pool and a shower open to the heavens. Your booking is inclusive of breakfast supplies and complimentary snacks, leaving more time for basking in the sun and drinking up the sea views.
Two guests, one bedroom
Price: $538 per night
Villa Asterope luxury retreat
With a panoramic heated pool, hot tub, sauna, and stocked wine cellar, this deluxe property is one of the best all-inclusive Santorini villa rentals. Breakfast is delivered daily to enjoy on the terrace while the host provides a round pick-up service and complimentary car rental. Located in the peaceful and lesser-visited Pyrgos Village, the rental is still less than five minutes to Fira (Thira).
Six guests, three bedrooms
Price: $1,511 per night
Canava Villas Winery Estate
This historic winery is the best Santorini Airbnb for large groups. The property has been reimagined as one of the best Santorini vacation rentals for larger groups. Spread over three villas, the complex is fitted with two outdoor pools, one of which features a cave nook. You’ll find sufficient sheltered areas for dining outside, Mediterranean-style, with mountain and sea views. Bedrooms are built into the original foundations of the cave residence with upscale bathing facilities and top-end bedding.
Fourteen guests, five bedrooms
Price: $920 per night
Airbnbs in Fira (Thira), Santorini
Three-bedroom villa with two caldera-view Jacuzzis
Once the home of a sea captain, this Airbnb in Fira, Santorini, has been regenerated into an exclusive cave villa in the heart of the island’s capital. Interiors revolve around archetypal Cycladic features with two terraces each with a hot tub overlooking the caldera. Breakfast and daily housekeeping are included in the rate while personal chefs, massages, and food delivery are available at a surcharge.
Six guests, three bedrooms
Price: $619 per night
Opera Mansion – villa with outdoor and indoor pool
This cave-style Santorini Airbnb with private pools, an outdoor hot tub, and a steam room is perfect for honeymooners. Appointed with swanky furnishings and monochrome decor, the living spaces are an easy match for the lush terrace with a sea view. Drop down to the subterranean wine cellar and dining zone in the evening for a romantic dinner cooked by a Thira-based chef.
Four guests, one bedroom
Price: $494 per night
Coat of Arms Mansion – luxury on the caldera
Encompassing the main house and a guest apartment, this Airbnb in Fira, Santorini, with a hot tub is suitable for a trip of couples or two families. Constructed in 1830, the villa displays Venetian exteriors and contemporary interiors with period furnishings following a recent facelift. Terraces with bougainvillea provide protection from the fierce sun and are a delight for morning coffee through to al fresco suppers. Consider hiring a local chef to elevate the experience.
Six guests, three bedrooms
Price: $802 per night
Airbnbs in Oia, Santorini
Cave villa with heated plunge pool and caldera view
This Airbnb in Oia, Santorini, with a private plunge pool overlooks the Aegean Sea and the two volcanic islands, Palia and Nea Kameni. The bedrooms and living room are minimalist, with full emphasis on traditional Cycladic architecture and unparalleled sunset views. One bathroom is fitted with a rainfall shower and the second with a soaking tub. Breakfast is supplied every morning to the villa.
Four guests, two bedrooms
Price: $420 per night
Santorini paradise: Paradise and Helios cave houses
One of the coolest Santorini vacation rentals, this duo of picturesque whitewashed homes are brought to life with kooky pieces of art and intricately tiled bathrooms. The terraces and hot tubs survey the glamorous village of Oia and grant an unobstructed view of the famous sunset viewpoint. After hours, you can clamber down the ladder to your own little cave winery – designed to resemble a Greek tavern.
Nine guests, three bedrooms
Price: $602 per night
Pina Caldera
If you like piña coladas, book this cave-house Airbnb in Santorini with a private pool, pronto! This traditional Cycladic dwelling has been renovated with modern luxuries while preserving its heritage legacy. The highlight is the partially covered exterior plunge pool with a whirlpool feature overlooking the volcano. This spills onto the sun terrace where you can top up your vitamin D and live like an A-lister.
Two guests, one bedroom
Price: $665 per night
Traditionally renovated cave house
What was once the bakery of Oia has been restored into this extraordinary cave house vacation rental. Accented by red pumice stones, antique marble floors, and handcrafted wooden furniture, the space feels homely. A skylight in the middle of the central dome floods the interiors with the Mediterranean sunshine while the private cave pool is partially covered. Dubbed the “dome of awesome” by one happy guest, this is one of the best cave Airbnbs for families in Santorini.
Three guests, three bedrooms
Price: $503 per night
Airbnbs in Perissa, Santorini
Santorini Mystique Garden
Cast yourself to the quieter half of the island at this Airbnb in Perissa on Santorini’s southeast coast. Nature mingles with luxury in a garden teeming with bougainvillea, palms, and hibiscus while the private pool is sizable enough for getting some laps in. Bedrooms are simple with emphasis placed on comfort and there’s a charming kitchen where you can flex your meze-making skills – or outsource to a local chef.
Six guests, three bedrooms
Price: $685 per night
Modern Dome Homes – The Mint
This two-story Airbnb in Santorini with a private pool and outdoor Jacuzzi peers over the Aegean Sea and is a short walk or drive to the Greek island’s black beaches. Interiors channel a homely vibe through the careful selection of linens, art, and decorative trinkets. The host goes the extra mile by stocking the pantry prior to arrival and will work with you to personalize your stay for a special occasion such as a honeymoon or birthday.
Five guests, two bedrooms
Price: $331 per night
Aeolis Santorini holiday house with an amazing pool
This five-bedroom vacation home is another contender for one of the best Santorini villa rentals for larger groups and wedding parties. The swimming pool is equivalent to half Olympic size, making it one of the largest on the island – with a bridge for honing your finest belly flops! Daily housekeeping is included in the rate and the host can arrange breakfast, tours, and spa treatments upon request.
Fourteen guests, five bedrooms
Price: $953 per night
Airbnbs in Kamari Beach, Santorini
Rustic patio suite near Santorini black-sand beach
A ten-minute walk from Kamari Beach, this cozy suite is countrified with wooden beams and barn doors. Perfect for a couple, the space comprises a lounge, kitchenette, and bathroom with a mezzanine bedroom in the loft. Out on the patio, a private hot tub awaits plus deck chairs and a swing seat. The host will arrange traditional Greek breakfasts and cooked meals to enjoy on the terrace for a surcharge.
Two guests, one bedroom
Price: $180 per night
Oceanfront villa with magical sunsets
Wake up to the sound of the waves at this modern beachfront villa with direct access to the sea from the private porch. The yard is landscaped with shrubs and plants, with your own Jacuzzi overlooking the shore – remember to grab a bottle of vino from the winery next door and you’re all set for sunset. Furnished with a fitted kitchen and tons of closet space, this is one of the best Airbnbs for a long-term stay.
Four guests, one bedroom
Price: $248 per night
Kamari Beach villa with private heated pool
Comprising two en suite king-size bedrooms plus a sofa bed in the lounge, this family-friendly Airbnb is in the heart of the village. Beautifully decorated with Santorini trinkets and natural woods, this bright and airy villa has a soothing aesthetic. The rental unit includes a fully equipped kitchen with an oven and stovetop while the yard contains a pool with whirlpool features. All this, moments from the beach, local eateries, and buses.
Six guests, two bedrooms
Price: $460 per night
Airbnbs in Firostefani, Santorini
Cycladic home with caldera views from the Jacuzzi
Located on the periphery of Fira (Thira), in the village of Firostefani, this stylish vacation home plucks different elements from Greek and European interior design. With step-free access from the street, the rental is suitable for wheelchair users or guests with mobility concerns – a rare find in Santorini. Although not pictured, the apartment does have a kitchen and the hosts are on hand to arrange deliveries from recommended taverns and bakeries.
Two guests, one bedroom
Price: $407 per night
James Bond-style cave with two plunge pools
Check into Villa Cloud and one day you might be able to say you slept at a Bond filming location. Chiseled into the volcanic soil, the interiors are lit by a surreal lighting concept with sound motion and optical illusions. The hot tub on the upper level floats above the first floor with a glass bottom while a trick mirror in the bedroom suggests the presence of water above the bed. Located in Firostefani, you’re tucked away in a tranquil spot within walking distance of the capital.
Three guests, one bedroom
Price: $727 per night
Sunset and caldera view Santorini villa
With a view like this, why even leave your Airbnb? Elevated over the caldera, the sun deck is fitted with a hot tub and pergola equipped for dining and snoozing. In fact, this is one of the largest private terraces on the island. Two of the three bedrooms are cocooned within the cave complex while the bathroom of the master suite has a tub etched into the walls. Traveling chefs can rustle up an al fresco feast in the American-style kitchen with all the trimmings.
Six guests, three bedrooms
Price: $794 per night