Vacation rentals in Pyrgos Kallistis

Olyra Traditional Cave Houses

The traditional residences Olyra Traditional Houses, are in the heart of the medievial settlement of Pyrgos, very close to the imposing Kasteli (castle). A three minute walk in the stone laid pavements and side strees is enough to go from Olyra to the central parking of the village as well as the central square. Our houses are created in the same place where the bakery of the village was two centuries ago, with great respect and attachment to Santorinis¨ architecture. The decoration is character

Santorini Sky | The Lodge *Most Unique*

SPECIAL 2026 RATES! Heaven has a new address! This sensational villa, blends rustic design with modern comfort and luxury. From the private infinity jacuzzi, to marble counters, pillow-top king-size bed, and satellite TV – Every detail has been considered to make The Lodge is as stunning inside as the views are outside. And at the top of the ‘stairway to heaven’ lies the Sky Bedroom which will absolutely take your breath away – the most spectacular private rooftop terrace on the whole island.

The Cove | Beach House (Upper)

Escape to serenity with the soothing sounds of waves and the elegant ballet of boats, a legacy crafted by our family's mariner ancestors in the late 19th century. Nestled less than 10 steps from the water, the house rests in perfect harmony with nature and provides an ideal spot to unwind and relax. Eco-friendly and freshly renovated in 2022. What sets us apart is our commitment to annual maintenance, ensuring a perpetually refreshed haven. Explore the timeless allure of coastal living with us!

Martynou View Villas

Martynou View villas is a private property,located in Santorini Pyrgos village. Just a few steps away from restaurants cafe and more shops.Only 10 minutes driving distance from central Fira and from the best beaches of the island. This is an ideal choice for couples. The property offers a spacious living room with kitchen, bathroom,double bed,air condition,coffee machine,TV,fridge,Wi-fi, soundtrack,private parking and a lovely balcony with private heated jacuzzi and stunning sea view!

Folia Cave house

Traditional troglodyte house at ‘the top’ of Pyrgos's medieval village, renovated and furnished in a cool bohemian style with amazing panoramic views. Every detail has been thought through. Prime location, a hidden gem in the village. Steps away from restaurants, bistros, local shops, cobbled streets and blue and white domed churches. The house is spacious, stylish and unique. A luxury jacuzzi is situated in the walled courtyard allowing you complete privacy and a sense of calm.

Faros Villa Guest House

Experience a truly unique stay in our Cycladic sea house, where history meets comfort. Nestled on a hillside, this remarkable retreat features a bed constructed within the ancient stone walls. Sleep surrounded by the echoes of the past, as the soothing sounds of the sea lull you into a peaceful slumber. Wake up to breathtaking views from every angle, as the sun casts its golden glow on the shimmering waters. Breathtaking sea views surround you, inviting tranquility and serenity.

Deluxe Villa~Heated Plunge Pool& Panoramic Seaview

Picture yourself relaxing in the white-washed UNESCO-listed town of Pyrgos - Santorini’s highest point - where you can watch the sun set behind a volcano with a glass of wine in hand after enjoying some sizzling saganaki, fresh seafood and salad at a nearby local restaurant. Our especially designed villa, in a village that has not changed through times, will definitely meet your demands as you can enjoy the private balcony complete with a hot tub and panoramic island views.

Star Infinity Suite with private heated Jacuzzi.

Star Santorini Infinity Suites is brand new complex of 3 suites each one with private heated jacuzzi and one shared swimming pool. An exclusive location provides a marvelous seashore&mountain landscape. This Suite is with two bedrooms (one bedroom is loft style bedroom). Two bathrooms,one living area with kitchenette,two balconies,one private jacuzzi and one shared swimming pool. Breakfast (Greek natural products) is provided with extra cost of 15 euro per person per day.

The Colourful Land Syrma

The Colourful Land "Syrma" is a partly cave-like boat house, fully transformed on 2022 that offers comfort, relaxation and wonderful view of Western Milos hills. The values of Cycladic architecture combined with a touch of luxury defined the design philosophy. The unified vaulted interior welcomes you with kitchenette, living room and highly eleveted king size bed which are connected with the bathroom. Surraunded by archeological hills and belong to the sea.

Demeter Cave House – Luxury Adults-Only Cave House

Perfect for honeymoons, anniversaries, or a romantic escape. Demeter Cave House is Santorini’s award-winning couples’ hideaway where Cycladic tradition meets calm, contemporary design. Set in Pyrgos, a lively village with a great local vibe, you’re moments from sunset bars and tavernas without the intensity of Fira or Oia - yet still tucked away in your own private cave house, with a jacuzzi and huge terrace. Authentic. Private. Perfectly placed.

Bluewhite villa with heated private pool

Situated in the traditional village of Pyrgos Kallistis, the heart of Santorini island, my place offers a stunning panoramic view of sunrise and the Aegean Sea. The 130m² Villa features luxury, privacy, easy access and comfort in Cycladic style combined with modern design and decoration. Our new infinity pool is a must! Please note that the pool is functional only for the spring and summer season March 15- October 31st

Almi Guesthouse: a tiny gem, literally on the sea

Welcome to Almi Guesthouse, a tiny jem, literally on the sea. The guesthouse consists of a single open space with a traditional dome ceiling and a bathroom, a total of 18sqm. Outside there is a paved little yard which leads to the edge of the rocks. The building was reconstructed in 2019 and it is located on the underside of the road that connects the Bridge with the gates of the Castle, near Kourkoula, a natural pool.