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Cycladic house vacation rentals in Pyrgos Kallistis

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Top-rated cycladic house rentals in Pyrgos Kallistis

Guests agree: these cycladic house rentals are highly rated for location, cleanliness, and more.

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Guest favorite
An outdoor terrace features a private heated Jacuzzi and sun loungers, framed by traditional Cycladic architecture. Soft, neutral tones are complemented by gentle lighting. A wooden ladder leans against the wall, leading to the upper level, while distant white buildings create a scenic backdrop.
Cycladic home
4.95 out of 5 average rating, 304 reviews

Helianthus Honeymoon Hideaway House

Our Honeymoon House with Caldera View offers the perfect romantic escape in Santorini, with the graceful addition of a heated outdoor Jacuzzi (will be closed between 15/11-15/3) providing the ultimate sense of relaxation overlooking the majestic caldera and the infinite Aegean blue. In an ample space of 40m2 divided into two levels, it provides everything a couple may desire. It has been built in perfect alignment with the distinct Cycladic architecture and boasts unparalleled, absolute privacy

Top guest favorite
A private heated pool is seen on a terrace, offering unobstructed views of the deep blue sea and distant islands. The scene includes iconic white buildings with blue domes, set against a clear sky, showcasing typical Santorini architecture.
Cycladic home
4.95 out of 5 average rating, 370 reviews

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

Guest favorite
The private veranda features a hand-paved stone floor, offering unobstructed views of the sea and caldera. Two deck chairs invite relaxation under the bright sky, alongside a small dining table with wooden chairs. The serene atmosphere highlights the natural beauty of the surroundings.
Cave
4.97 out of 5 average rating, 294 reviews

Historic cave house, the old bakery by Cycladica

The old bakery of the village awaits just two minutes from Oia's central square, with a private entrance right on top of the stairs that lead to Armeni bay. Carved in the mountain with respect to the unique local architecture and in harmony with the sun-filled, wild volcanic beauty, the newly restored cave house recounts stories of tradition, heritage and style. The red pumice stones, antique marble floors and handcrafted wooden furniture, create the feeling of an authentic warm hospitality.

Top guest favorite
A private terrace features a refreshing plunge pool surrounded by whitewashed walls and wooden lounge chairs. Plush pillows are arranged on a nearby seating area, while the iconic blue domes of Oia are visible against the clear sky, overlooking the expansive sea.
Guest suite
4.98 out of 5 average rating, 213 reviews

Suite with Outdoor Plunge Pool & 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. This suite additionally features a private outdoor plunge pool. The view from its terrace is stunning, featuring the caldera and the two iconic blue domes of Oia. Santorini International Airport is about 17 km from Oia Spirit Boutique Residences, and the Ferry Port at approximately 23 km.

Top guest favorite
A private jacuzzi overlooks the Aegean Sea, with panoramic views of the coastline and cliffs in the distance. Comfortable seating is positioned nearby on a sunlit terrace, creating a serene environment to enjoy the sunset and surrounding natural beauty.
Cycladic home
4.99 out of 5 average rating, 225 reviews

Anemi Lovers House - Sunset and Sea View

A place to let the rest the world slips away. The ideal intimate escape! Anemi Villas is a beautiful example of the traditional Cave and Sea Captain Houses of Santorini, carved in the rocks of the magnificent caldera with panoramic views of the Aegean Sea, the Caldera Views and the famous Sunset of Santorini, It gives you the feeling of walking into a living postcard! Offering exceptional concierge service, Anemi Villas can turn your Holidays into an unforgettable life time experience!

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
4.95 out of 5 average rating, 205 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.

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
4.92 out of 5 average rating, 166 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
4.88 out of 5 average rating, 188 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 private jacuzzi is seen on a sunlit terrace, surrounded by whitewashed walls. The clear water reflects the blue sky, offering views of the tranquil Aegean Sea and the village below. Nearby, a dome of a traditional structure is partially visible in the distance.
Cycladic home
4.94 out of 5 average rating, 156 reviews

NG Maisonette Private Jacuzzi

Welcome to Maisonette, a stunning traditional Santorini house located in the charming village of Kontochori. Featuring a private jacuzzi with incredible Aegean views, a cozy living room with a smart TV, and a fully equipped kitchen, this house is the perfect combination of traditional Cycladic style and modern minimalism. The bedroom is located inside a cave with a smart TV, accessed via a few stairs, and a hall with a desk filled with natural light.

Top guest favorite
A spacious bedroom is showcased, featuring a large bed with a dark gray blanket. The open layout reveals a bright living area with a kitchenette and seating space, all adorned in soft white tones. Large windows invite natural light and provide views of the surroundings.
Cycladic home
4.93 out of 5 average rating, 449 reviews

Divine View Sun Home

Unwind and relax with a glass of wineadmiring the breathtaking views of the famous Santorinian sunset from this house's private veranda . Awake refreshed and ready for a day to explore the island via this clean, sunny house with impressive views to the caldera , volcano of Santorini Aegean Sea & the island of Thirassia . Head out and wander through the famous paths of Fira and explore the nearby little shops & cafe .

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
4.96 out of 5 average rating, 284 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.

Top guest favorite
A wooden sign displaying the name 'Olyra Traditional Cave Houses' is mounted on a whitewashed wall, complemented by a rustic gate. Vibrant pink flowers enhance the entrance, adding a touch of natural color to the setting.
Cycladic home
4.96 out of 5 average rating, 149 reviews

Olyra Traditional Cave Houses 2

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.

Popular amenities for Pyrgos Kallistis cycladic house rentals

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Avg. price€ 166€ 155€ 139€ 138€ 145€ 173€ 217€ 238€ 172€ 128€ 131€ 143
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Quick stats about cycladic house rentals in Pyrgos Kallistis

  • Total vacation rentals

    Explore 6,220 vacation rentals in Pyrgos Kallistis

  • Nightly prices starting at

    Pyrgos Kallistis vacation rentals start at € 17 per night before taxes and fees

  • Verified guest reviews

    Over 198,960 verified reviews to help you choose

  • Family-friendly vacation rentals

    3,450 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 1,710 rentals that welcome pets

  • Vacation rentals with a pool

    1,370 properties feature pools

  • Rentals with dedicated workspaces

    2,040 properties have a dedicated workspace

  • Wi-Fi availability

    5,970 of Pyrgos Kallistis vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pyrgos Kallistis rentals

  • 4.9 Average rating

    Pyrgos Kallistis stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Pyrgos Kallistis's top spots, include Temple of Demeter, Naousa, and The Dunes Course

Destinations to explore