Cycladic house vacation rentals in Pyrgos Kallistis

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Top-rated cycladic house rentals in Pyrgos Kallistis

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Top guest favorite

A private terrace features comfortable seating with plush cushions, small wooden table, and decorative bottles. The space provides a clear view of the deep blue ocean and surrounding caldera, complemented by the whitewashed buildings of Oia in the background and a bright blue sky.

Guest suite in Oia

4.99 out of 5 average rating, 201 reviews

Suite with Blue Domes View

Located in the very heart of Oia, at a secluded position on the famous caldera of Santorini, Oia Spirit is a stylish complex of 8 stand-alone traditional cave houses, with access to a shared cave pool. Right out of a post card between the two iconic blue domes of Oia. This suite has a private terrace with astonishing panoramic view to the caldera and the blue domes. Santorini International Airport is about 17 km from Oia Spirit Boutique Residences, and the Ferry Port at approximately 23 km.

Top guest favorite

A heated plunge pool is featured within a uniquely shaped archway, with clear blue water reflecting the sun. A stunning view over the ocean and distant islands is visible through the opening. Decorative cushions and a small table with refreshments enhance the inviting atmosphere.

Villa in Imerovigli

4.99 out of 5 average rating, 147 reviews

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.

Top guest favorite

A Greek Fisherman's House is depicted, featuring a white exterior with a red-tiled roof and three sets of blue windows, facing the beach. The surrounding area includes lush greenery, and additional buildings can be seen in the background against a clear blue sky.

Tiny home in Gytheio

4.96 out of 5 average rating, 109 reviews

Authentic Greek Fisherman's House 1 - Summer Love

Please also check "Love House" and "Love Nest" Houses for availability. House is on the beach. This place is good for couples, solo adventurers, LGBTQ+ firiendly, business travelers and pet firendly. You will wake, eat, live, sleep, dream on the beach! Place is unique, it is like living on a Yacht with the luxury of a house. It is an Authentic Greek Fisherman's House, used to be an Inn and a family house later on. Now it is divided in three separate houses, sharing the same beach.

Top guest favorite

A private infinity pool is situated on the terrace, offering unobstructed views of the sea and surrounding hills. The pool water reflects the sky, while lush greenery and rocks frame the area, creating a serene environment.

Cycladic home in Pyrgos Kallistis

4.95 out of 5 average rating, 195 reviews

Delilah Villa with outdoor swimming pool

H Delilah Villa μπορεί να φιλοξενήσει 5 άτομα, έχει 2 κρεβατοκάμαρες με διπλό κρεβάτι, και ένα καναπέ στο σαλόνι. Έχει ιδιαίτερη διακόσμηση και ένα μεγάλο μπάνιο με ντουζιέρα. Η βεράντα του είναι πολύ μεγάλη με υπέροχη θέα, ιδιωτική πισίνα, καθιστικό και ξαπλώστρες. Ακριβώς μπροστά στη βίλλα υπάρχει ιδιωτικό πάρκινγκ . Ήσυχη γειτονιά με ιδιωτικότητα και υπέροχη θέα. Είναι επίσης πολύ κοντά στη πλατεία του Πύργου , μόλις 200 μέτρα, στην οποία βρίσκονται η αγορά , τα εστιατόρια και τα καφέ.

Top guest favorite

A private plunge pool is visible in the foreground, reflecting clear blue water. The stunning caldera view features vibrant blue dome churches in the distance, with the Aegean Sea stretching out toward a clear sky. Whitewashed buildings create a serene backdrop.

Cycladic home in Oia

4.99 out of 5 average rating, 270 reviews

Santorini blue, caldera views, private pool

Traditional Santorini cave house with famous blue dome churches, postcard perfect caldera views in the heart of Oia. next to main path.. Private plunge heated pool with panoramic views. Next to Island blue, Serenity &Eternity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities Other villas : Island blue, Eternity,Serenity,Captains blue, Secret garden, Sailing &Sky blue Flexible on pandemic related cancellations!

Top guest favorite

Two white, high-back stools are positioned beside a railing overlooking the sea, with a scenic view of rocky shores and distant mountains. A decorative tray holds two cups, complemented by a pair of sunglasses resting nearby, suggesting a relaxed outdoor environment.

Cycladic home in Milos

5 out of 5 average rating, 102 reviews

Milos By The Sea - Eco House

"Milos By The Sea" is a brand new, traditional solar powerhouse, 100% eco-friendly, located in a fishing village only 600 meters from Plathiena beach. It is an Eco friendly house as it is completely powered by solar energy. The picturesque settlement called "Areti", provides an exquisite view, since it is surrounded by the beauty of nature. Waking up to the sound of the waves is a unique experience for our guests who need to enjoy absolute tranquility during their vacation.

Guest favorite

A person is seated on a terrace overlooking a vibrant sunset. The view includes distant hills and the sea, while a rustic table holds a variety of fresh fruits. A glass holds a drink, reflecting the warm colors of the sunset.

Dome in Pyrgos Kallistis

4.93 out of 5 average rating, 157 reviews

Calliope's Villa with jacuzzi

Calliope's villa, featuring a jacuzzi and stunning sea views, is located in the charming village of Pyrgos, just 100 meters from the main square, where you'll find restaurants and supermarkets. Santorini's city center (Fira) is only a 10-minute drive away (5 kilometers). This fully equipped, two-story house is ideal for families and groups of friends, offering 3 bedrooms, 2 living rooms, 2 bathrooms, 2 kitchens, a relaxing jacuzzi and a magical view from the upper floor.

Guest favorite

A private pool is shown, with crystal-clear water reflecting the sky. A wooden table holds a platter of fresh fruit, including watermelon, grapes, and banana slices, alongside two glasses. Scenic views of the surrounding hills and coastline are visible in the background.

Guest suite in Pyrgos Kallistis

4.88 out of 5 average rating, 179 reviews

View from Above 1

The luxury Santorini villa will be your private paradise for the summer!Located in Pyrgos Kaliistis, right in the middle of the island, it offers panoramic views and the chance to be wherever you want to in no time! It is perfect for 2 adults! The villa features 1 cozy bedrooms, 1bathrooms, a fully-equipped kitchen with all modern appliances, LED TV. The outdoor areas feature a private pool (with dimension 2 * 1.5 meters a fantastic sea views and 2 sun chairs

Guest favorite

A figure stands at the edge of an infinity pool, silhouetted against a vibrant sunset over the caldera. The calm water reflects the warm colors of the sky, creating a serene atmosphere that enhances the natural beauty of the surrounding landscape.

Cycladic home in Megalochori

4.98 out of 5 average rating, 141 reviews

Ambeli Sunset/private heated pool & breakfast

Ambeli Sunset Villa's unique allocation provides the famous sunset view of the caldera avoiding the overcrowding of the well-known cities of Santorini. A newly anti-seismic constructed building covering all the official guidelines to maximize the security of our guests. Depending on the chosen room type that fits you, guests will experience the use of the heated pool or the hot tub in maximum privacy as no facilities are public.

Top guest favorite

An infinity pool gently merges with the shimmering caldera below, framed by an elegant archway. The water reflects a tranquil blue, inviting relaxation while offering sweeping views of the volcanic landscape that surrounds.

Cycladic home in Akrotiri

5 out of 5 average rating, 204 reviews

Akrorama Anemos - Private Pool & Caldera View

Anemos suite is located in Akrotiri overlooking the caldera and the volcanic islands . It is a suite with Private, Infinity heated Cave style plunge pool with Jet system and private patio. There is a king size bed that can accommodate two person. Daily breakfast is included and served in your suite . There is a cleaning service included. Inform us about your arrival details in advance , we can arrange a taxi/transfer for you.

Guest favorite

A charming courtyard is surrounded by whitewashed buildings with blue accents. A staircase leads to a balcony on the second level, while various architectural elements create a distinct and inviting atmosphere. Lush greenery and a glimpse of a turquoise dome contribute to the serene setting.

Apartment in Antiparos

4.93 out of 5 average rating, 116 reviews

Antiparos House in the Kastro

It was built by the Venetians in the 15th century as a part of a complex of 24 houses joined into a square defensive form that surrounded and protected the main tower that used to be there. This complex of houses is called 'Kastro' meaning castle. The house retains all charm from the past and offers the ideal holiday house. This cozy house is located in the heart of the village of Antiparos.

Top guest favorite

An illuminated cave pool is surrounded by smooth curves of stone walls, highlighting the modern design. The warm water reflects soft blue tones, creating a serene ambiance in the space. An indirect light source enhances the unique features of the pool area.

Cycladic home in Pyrgos Kallistis

4.96 out of 5 average rating, 273 reviews

Santorini Mayia Cave House with Private Cave Pool

Discover the real Santorini, beyond the crowded touristic routes. Mayia Cave House is a renovated 19th century traditional cycladic cave house in the quiet medieval village of Pyrgos. Offers all modern amenities, a spectacular private large warmed cave pool, a private hot tub in the terrace and incredible views over Santorini, including the famous sunset.