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Cycladic house vacation rentals in Santorini Caldera

Find and book unique cycladic house rentals on Airbnb

Top-rated cycladic house rentals in Santorini Caldera

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

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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 Merovígli
4.99 out of 5 average rating, 172 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.

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Top guest favorite
An outdoor terrace offers a jacuzzi and comfortable seating, perfect for relaxation. Expansive views of the caldera and surrounding landscape are visible, showcasing the natural beauty of Santorini. The clean, modern layout encourages outdoor enjoyment while highlighting the tranquil setting.
Cycladic home in Santorini
4.98 out of 5 average rating, 250 reviews

Sol

I-Sol is an isolated house in the center of the traditional village of Akrotiri! It has a two level outdoor! At the first level where is the entrance of the house you can relax on the dinning couch watching the caldera view! At the second level you will enjoy the sun and a 270 degrees view including the volcano relaxing at many choices such us the jacuzzi or the big sun beds or a couch or Acapulco style lounge chairs. Inside the house is a fully equipped kitchen , bathroom and two bedrooms!

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Top guest favorite
A rooftop terrace offers vibrant seating in two orange chairs, complemented by a round yellow table. Scenic views of the Aegean Sea and nearby islands are visible, along with several ships in the distance. A colorful blanket and two drinks enhance the setting.
Cycladic home in Santorini
4.99 out of 5 average rating, 136 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

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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
4.97 out of 5 average rating, 310 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!

ValueFamilyNearby

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, 229 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, and the Ferry Port at approximately 23 km.

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Top guest favorite
Guest suite in Pyrgos Kallistis
4.89 out of 5 average rating, 201 reviews

Luxury Suite| Private Infinity Pool & Volcano View

Enjoy complimentary breakfast delivered to your suite every morning. Relax by your private infinity pool, exclusively reserved for your stay, while admiring breathtaking panoramic views of the volcano, the Aegean Sea and Santorini. Due to the open caldera hillside setting ,the pool area may be visible from some surrounding outdoor areas due to the open caldera setting. Perfect for couples seeking tranquility, comfort and unforgettable sunsets.

FamilyValueSleep quality

Top guest favorite
An infinity pool with crystal-clear water reflects the serene sky, framed by a curved architectural feature. The pool seamlessly blends into the view of the caldera and volcanic islands, providing a tranquil setting for relaxation.
Cycladic home in Akrotiri
5.0 out of 5 average rating, 231 reviews

Anemos suite -Private infinity pool & patio

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.

ValueLocationView

Guest favorite
An outdoor area features a stonewall backdrop with a staircase leading to a door. A circular hanging chair and a dining set with gray chairs are present. Cushions are arranged on a raised platform, while a tray with fruits is placed on the table.
Cycladic home in Megalochori
4.93 out of 5 average rating, 178 reviews

Antonio Caves

Antonio Caves are a typical example of Santorinian architecture. Constructed in 1901, it was initially used as cave house wine preparation cellar and a bakery built right into the volcanic rock. In 2020 it was renovated completely and converted into 3 autonomous suites sharing a common courtyard Situated in the traditional village of Megalochori in two minutes walking distance from the picturesque square of the village

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Superhost
An infinity pool glistens in the sunlight, with a wooden pergola providing shade over a lounge area. The surrounding landscape is characterized by hills and a clear blue sky, enhancing the serene atmosphere of the villa.
Cycladic home in Santorini
4.83 out of 5 average rating, 115 reviews

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

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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 in Fira
4.93 out of 5 average rating, 483 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 .

ValueLocationSolo travel

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, 302 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.

LocationFamilyHospitality

Superhost
A whitewashed exterior is illuminated by soft lighting in the evening. Stone stairs lead to a multi-level space with an outdoor dining area featuring a parasol and decorative plants. A heated jacuzzi is visible, integrating nature and design harmoniously.
Apartment in Mesaria
4.93 out of 5 average rating, 202 reviews

Radiant Santorini Standard

The beautifully decorated Standard Suite with a zen vibe has two bedrooms with a cozy double bed in the first , a build-in double bed in the second and an extra sofa bed, fully equipped kitchen and bathroom. Guests also enjoy premier modern amenities such as high speed Internet and flat screen TV. Outdoor heated jacuzzi also provided.

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