Unique Vacation Rentals in Santorini’s Most Picturesque Towns

Fancy sleeping in a cave house with a view of an ancient volcano? Take your vacation to a whole new level with these unique vacation rentals in Santorini that guarantee a stay like no other! The shift towards unique travel experiences has never been clearer than what today’s tourism trends convey. More and more travelers […]

Fancy sleeping in a cave house with a view of an ancient volcano? Take your vacation to a whole new level with these unique vacation rentals in Santorini that guarantee a stay like no other!

The bathroom of a unique vacation rental in Santorini
The bathroom of a unique vacation rental in Santorini | Photo credit: Twin Cave House

The shift towards unique travel experiences has never been clearer than what today’s tourism trends convey. More and more travelers are undoubtedly yearning for authenticity and memorable stays. In Santorini, that promise is fulfilled with accommodations that rival the island’s iconic and distinct Caldera. 

From creative cave houses offering panoramic views of ancient volcanoes to sophisticated modern retreats, each of these unique vacation rentals in Santorini tells its own story of luxury and exclusivity. As we explore the island’s beautiful capital and its picturesque villages, prepare to discover places where every detail reflects the true magnificence of Santorini.

Fira: Unique Vacation Rentals in Santorini’s Beautiful Capital

As the island’s bustling capital, Fira complements its stunning views and historic streets with some of the most unique charming vacation rentals in Santorini. 

Here are three of the best options in the city:


This expansive, fully-restored cave house covers 3,000 square feet, combining sleek contemporary aesthetics with the rustic charm of yesteryear. Each of the two master suites offers king-sized beds, with an additional room that can serve as a lavish living space or an extra bedroom. 

Furthermore, the high-end bathrooms feature rain showers carved directly into the rock, enhancing the authentic cave-dwelling experience. Finally, a spacious private veranda, complete with a pool, BBQ, and cozy sunbeds awaits outside as you soak up the Santorinian sun.


The Coat of Arms Mansion is a testament to luxurious living right in the heart of Fira. This villa exudes a noble charm with its spacious interiors, including three bedrooms and two living rooms, all adorned with chic decor. 

And the best spot? The terrace, no doubt, offering spectacular sea views, perfect for a morning espresso or evening wine. In addition, wellness packages are also available on-site, including yoga and fitness classes, making it a perfect stay for those seeking that much-needed R&R. 


Just a short walk from Fira’s charming streets, the Sea Horse Residence provides a tranquil yet convenient sanctuary for discerning guests. Recently renovated, this property preserves the quintessential Cycladic architecture with its white-washed walls and simple, elegant lines. 

Also offering breathtaking views across the Caldera from Oia to Akrotiri, guests can certainly indulge in the changing hues of the sea and sky from dawn till dusk.

You might also like to read: Top Wedding Venues in Santorini

A living area with couches and a wooden round table of a house in Santorini
A living area of a house in Santorini | Photo credit: Villa Filon

Oia: Unique Vacation Rentals in Santorini’s Postcard Village

Synonymous with its iconic blue-domed churches and the sun setting into the Aegean, Oia is often touted as Santorini’s living canvas. Here, quaint accommodations serve as a portal into the magic of the island, offering unique experiences that fuse luxury with local lore. 


A stunning spot by the cliff, 270 Oia’s View Cavehouse VII offers a spellbinding retreat. The property boasts a private swimming pool, ingeniously carved into the mountain, providing panoramic views of the surrounding Aegean islands and the famed Santorinian sunset. 

The villa’s layout includes a spacious living room, and a dining area with a fully equipped kitchen, all designed to maximize the awe-inspiring views. Interestingly, the master bedroom is located in a separate smaller cave. The room features a luxurious hydro-massage shower, emphasizing ultimate privacy and relaxation. Furthermore, the villa’s minimalistic decor is accented with bright colors and ambient lighting, complementing Oia’s natural beauty and scenic landscape.


A stone’s throw from Oia’s Venetian castle, the recently renovated Twin Cave House offers a distinctive stay right on the cliff’s edge. This property combines traditional Santorinian architecture with modern amenities. Featuring two separate but interconnected cave rooms, each with its own entrance, the ensemble is ideal for couples seeking privacy or families desiring connected quarters. The first room serves as a cozy bedroom with a basic kitchenette, while the second, larger room houses a full kitchen, dining area, and additional sleeping loft. 

Guests can marvel at the breathtaking caldera and volcano views from the house’s terrace, which also serves as a vantage point for Oia’s world-renowned sunsets. 

Pyrgos: Unique Vacation Rentals in Santorini’s Historic City

Nestled among the highest peaks of Santorini, Pyrgos retains its medieval charm and affords sweeping views of the island. With its fortress-like architecture and winding paths, a stay here guarantees a more secluded and authentic experience. 


Experience living in a beautifully restored traditional house with modern amenities at Villa Filon. With five spacious terraces that showcase views of the Caldera, the sea, and the countryside, opulence has never looked this good. The villa boasts an open-plan living lounge integrated into the iconic cave-style architecture, complete with a sumptuous corner sofa and state-of-the-art entertainment system. A winding staircase leads to a bright dining area and a fully equipped kitchen, perfect for entertaining guests. 

The highlight? A large spa jacuzzi on one of the terraces, providing a luxurious spot to unwind under the stars. With four elegantly designed bedrooms, Villa Filon is ideal for families or groups seeking a blend of communal areas and personal retreats. 


For those who prefer a more eco-friendly stay without compromising on luxury, the White Orchid Cave House & Studio stands out. Perched close to the artistic hub of Art Space Santorini, it features sustainable accommodations that include air-conditioned units with sea and mountain views. 

Moreover, the house is also equipped with high-end amenities and thoughtful touches like walk-in showers and coffee machines for a truly relaxing stay. What’s more, bicycle rentals and packed lunches are also available for exploratory day trips, guaranteeing an immersive visit to Santorini. So if you desire a tranquil yet active holiday on the island, White Orchid Cave House is where you should book your next stay.

The cliffside houses in Santorini
The cliffside houses in Santorini | Photo credit: Coat of Arms Mansion

Find Your Perfect Santorini Retreat with Casai

Beyond its famous sunsets and blue-domed churches, Santorini is indeed a mosaic of unique experiences waiting to be discovered. From the bustling streets of Fira to the tranquil charm of Oia and the historic allure of Pyrgos, our guide to unique vacation rentals in Santorini has highlighted places where each town’s character is as distinct as the accommodations themselves.

And remember, Casai is always here to help you find your perfect retreat, ensuring your stay is nothing short of spectacular. More than just a place to stay, our featured properties are also gateways to experiencing the island’s legendary beauty and culture.

Ready to experience Santorini like never before? 
Let Casai guide you to the most unique vacation rentals in Santorini. Plan your trip today and prepare for an adventure that will linger in your memories long after you’ve returned home.

Author: Katie

Katie strikes the balance between luxury and adventure, with a taste for the finer things and a spirit for solo travel. For her, indulging in the plush and posh isn't just a whim—it's the main event. Her stories are all about sharing those "treat yourself" moments, wrapped in witty banter and a keen eye for that next lavish escape that’s as unique as a secret handshake.

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