Vacation rentals with breakfast in Pyrgos Kallistis

Labyrinth Traditional Houses (Theseus)

Escape to the tranquility of the Labyrinth traditional house, nestled in the serene Pyrgos village. Immerse yourself in a fully renovated 18th-century retreat, a world away from the bustling crowds of Fira and Oia. Indulge in a complimentary breakfast and savor a traditional dinner prepared by our personal chef, all while admiring the breathtaking Santorini sunset. With concierge service, and timeless elegance, your unforgettable stay awaits. Book now and experience Santorini's enchanting beauty

Island blue, postcard perfect view & private pool

Traditional cave house located in the most famous location in Santorini Island with breathtaking postcard perfect views of the blue domed churches! 2 bedrooms, double beds 2 cave bathrooms. Outdoor heated pool with view! Next door to Santorini blue, Eternity & new home Serenity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities. Our other villas Santorini blue,Eternity,Serenity,Captains blue, Secret garden,Sailing & Sky blue

Three bedroom Villa with two Caldera View Jacuzzi

This luxury villa has the best location and feature specious terraces with famous view of Caldera and Aegean sea .Roof top terrace have heated Jacuzzi and comfortable sun-lounges.There is outdoor furniture next to Jacuzzi where you can enjoy breakfast and dinner with unforgettable view . Daily breakfast and cleaning make your stay comfortable .Each bedroom have private bathroom . In a walking distance you will find restaurants,bars, museums and supermarkets.Food delivery available.Free wi-fi

Olyra Traditional Cave Houses

Experience the essence of Santorini, where time stands still. Olyra is more than just a place to stay; it is a 200-year-old historic bakery, thoughtfully reimagined as a sanctuary of elegance within the medieval village of Pyrgos. Awaken in cave-hewn rooms and surrender to the magic of the sunset from our private rooftop, with the entire Aegean unfolding at your feet. Here, Dimitra’s warm hospitality and the village’s tranquil soul create the very experience others only ever find in pictures

Ventus Paradiso Villa, Outdoor Heated Plunge Pool

Our cave villa comes with sentimental value as it belonged to our grandmother. Dated back to 1920's brings a great heritage. The villa was totally renovated in 2015, transforming a traditional cave into a luxury residence following faithfully the unique cycladic architecture with exceptional modern esthetics. The villa consists of two bedrooms with ensuite bathrooms, a dining area and a small kitchenette. It features a heated plunge pool and an upper terrace with panoramic view over Caldera.

Infinity Pool • Luxury Villa • Sea View

Enjoy breathtaking sunsets and panoramic views of the Caldera, volcano and Aegean Sea from your private pool and terrace. Located in Pyrgos, Vista Dall Alto combines privacy, comfort and easy access to every corner of Santorini. The villa features 2 comfortable bedrooms, 2 modern bathrooms, a fully equipped kitchen and spacious indoor and outdoor living areas. Enjoy complimentary breakfast delivery and daily housekeeping while relaxing by your private pool and enjoying sunset views.

Santo Blue Horizon Villa | Jacuzzi | Caldera View

This unique villa is located in the heart of Oia in an excellent position and has stunning views. The famous Three Domes just in front of villa with panoramic view overlooking the santorinian caldera and the aegean sea, have magnetized visitors and photographers from all over the world, making it, the most popular spot in Santorini. The villa is in perfect harmony with the natural surroundings of the area and follows the principles of traditional Cycladic architecture.

Royal Penthouse • Sleeps 4• 8 min from Airport

A truly unique royal-style penthouse just 8 min from Athens Airport. Like a private museum, it features antiques, oversized 200×220 beds, a large private terrace, and access to the rooftop for panoramic views and plane spotting. Ideal for families, with plenty of space and character you won’t find anywhere else in the area. Glass doors flood the space with natural light and frame the open sky — a one-of-a-kind stay that blends classic charm with rare city views.

Cave Villa With Heated Plunge Pool & Caldera View

A traditional cave villa with modern touches that can accomodate up to four people with spacious veranda and breathtaking caldera views. Lathouri Cave Villa is perched on the famous caldera cliffside overlooking the Aegean sea and the two volcanic islands Palia and Nea Kameni. The traditional cycladic architecture along with the unique scenery makes it the perfect choice for those who want to enjoy a relaxing vacation in the lap of luxury.

Cottage house in olive grove

Cottage house in 10 acres olive tree grove, carefully decorated with upcycling wooden furniture customized from us. The house is located in a small settlement called Patima. It is 2 Km from Examilia Village, 6Km from the modern town of Corinthos and 4Km from ancient Corinthos. The center of Corinthos and the beach (kalamia) which have coffee shops, bars and restaurants are both 10 minutes by car from the house. All people are welcome.

Lioyerma Windmill Villa With Outdoor Hot Tub

At the edge of the traditional settlement of Oia, overlooking the Caldera and the world-famous Oia sunset, stands our fully renovated traditional Windmill, originally built in 1900. This unique three-level residence is connected by internal staircases and can comfortably accommodate a couple with two children or up to four adults. Breakfast is included, and free parking is available for all guests.

Serra | Caldera View Suite, Private Pool & Hot Tub

Perched above the Aegean, our newly built suites offer panoramic views across the entire Santorini Caldera—from the volcanic cliffs to Fira and Oia. Designed for refined Cycladic luxury, Serra combines modern comfort with authentic Greek hospitality. Relax on your terrace, unwind in your private pool, or soak in your heated jacuzzi while enjoying an elevated, unforgettable island stay.