Cycladic house vacation rentals in Santorini caldera

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Top-rated cycladic house rentals in Santorini caldera

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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 in Oia

4.95 out of 5 average rating, 290 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 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, 146 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.

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 in Oia

4.98 out of 5 average rating, 202 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 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, 192 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 spacious terrace offers panoramic views of the sea and nearby islands. Colorful chairs surround a round table, where drinks and snacks are lightly arranged. A person in a summer outfit gazes out at the landscape, framed by the vibrant colors of the furniture.

Cycladic home in Fira

4.98 out of 5 average rating, 119 reviews

Barocco Bello Villa

Welcome to Barocco Bello Villa The house is built inside a cave at Firostefani which means the "Crown of Fira". This area is one of the highest points on the Caldera giving it a unobstructed and magnificent view of the sea, the volcano and most of Santorini. The main city center Fira is a ten-minute walk along one of the most scenic roads of the island. Although a traditional house it contains the most modern amenities , and the interior design of the villa has a pop Baroque flavor

Guest favorite

An outdoor area features a private Jacuzzi surrounded by low seating and oversized cushions, positioned for scenic views of the caldera. The white structure blends harmoniously with the natural landscape, complemented by a shade sail that provides protection from the elements.

Cycladic home in Imerovigli

4.93 out of 5 average rating, 316 reviews

Pura Vida Cave House

When we acquired the Pura Vida Cave House it was a deserted Gem.. We immediately fell in love with the spot, on the top of a 300 meter cliff - nothing to block your sight but the end of the horizon. We put together a team to reconstruct it entirely, keeping the initial design of the house and blending it with modern touches and technology. The result is a Cycladic beauty, built into the rock, white as can be, to host a couple or a small family, in a fun and elegant environment!

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

4.98 out of 5 average rating, 266 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!

Guest favorite

A view from the terrace features a custom-built hot tub with clear water, surrounded by whitewashed walls. In the background, a traditional blue-domed church tower stands prominently against a serene sea and sky, capturing the charm of the Oia landscape.

Cycladic home in Oia

4.96 out of 5 average rating, 230 reviews

Bluedome Suite by Otium Villas & Suites

This is a newly renovated cavehouse that dates back to the 1890's. Situated in one of the most famous neighbourhood's in Oia "Monastiraki" next to the famous St Spyridon Bluedomes. It has been renovated keeping traditional cycladic cavehouse architecture at the forefront of the design while utilising modern building materials. This suite is ideal for couples and families. Its' minimal designed spaces inspire relaxation and comfort for the modern traveller.

Guest favorite

The private terrace features a dining table and reclining chairs, set against a backdrop of a golden sunset over the caldera. The expansive sea view includes distant hills and whitewashed buildings, creating a serene atmosphere for relaxation.

Cave in South Aegean

4.92 out of 5 average rating, 354 reviews

Soundscape - cave suite panoramic sea views

Within walking distance (only 7min walk) from Fira, the capital of the island, for shopping, museums and nightlife, Firostefani village is very peaceful and away from the crowds . There are plenty of things to explore on the island like museums, archaelogical sites, activities, beaches or just relax and enjoying the picturesque sea views plus that I am here to make sure you have everything you need and make you feel like home :)

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, 140 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, 200 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 spacious living area features a built-in sofa adorned with two decorative pillows. An adjacent sleeping area is partially visible, showcasing a double built-in bed with neutral bedding. Soft ambient lighting is provided by wall-mounted fixtures, emphasizing the smooth white walls and arched doorways.

Apartment in Mesaria

4.94 out of 5 average rating, 200 reviews

RadiantSantorini Junior Cave Suite With Jacuzzi

Junior suite is a traditional top-hill cavehouse with a double built-in bed and two built in sofa beds which combines luxury and high level privacy. With contemporary local interior design, soft lighting and great attention to detail, the Junior Suite provides the warmth, cleanliness and extra space for a perfect holiday experience. An outdoor heated jakuzzi and a stand-alone terrace will add relaxation to your summer dream.