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.
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- Top-rated all-inclusive and luxury Airbnbs in Santorini
- Airbnbs in Fira (Thira), Santorini
- Airbnbs in Oia, Santorini
- Airbnbs in Perissa, Santorini
Top-rated all-inclusive and luxury Airbnbs in Santorini
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
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
