Cycladic house holiday rentals in Santorini Caldera

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Top-rated cycladic home rentals in Santorini Caldera

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Top guest favourite
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, 381 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 favourite
A bright living area features white-washed walls and a spacious seating area with decorative pillows. Two wooden stools are positioned near a dark wooden coffee table. Large windows open to stunning views of the caldera, allowing natural light to fill the space.
Guest suite
4.95 out of 5 average rating, 218 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 balcony 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 favourite
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
4.99 out of 5 average rating, 157 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 favourite
Cave
4.97 out of 5 average rating, 296 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 favourite
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
4.95 out of 5 average rating, 167 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.

Guest favourite
A modern dining area features a wooden table set for four, accompanied by teal chairs. Soft lighting gently illuminates the adjoining bedroom through an archway, showcasing a spacious double bed with high-quality linens. A small potted plant adds a touch of greenery to the space.
Home
4.93 out of 5 average rating, 206 reviews

ASPRO luxury cave house

Located at the traditional Karterados area of Santorini, our traditional cave house, fully renovated in 2018, is a place where Cycladic architecture meets the luxurious accommodation. It is ideal for couples, families, friends and travelers wishing to live the unique experience of staying in a traditional Santorini cave house with all modern facilities. Centre of Fira town lies within 1,5 km (15 minute walking distance). Instagram: aspro_santorini

Guest favourite
A serene outdoor space features a small pool illuminated in soft blue, surrounded by white cave-style walls. A comfortable seating area with cushions is visible, alongside a decorative lantern casting a warm glow, creating an inviting atmosphere for relaxation.
Villa
4.97 out of 5 average rating, 174 reviews

MyBoZer Cave Villa

MyBozer Cave Villa is a traditional cave style house located in traditional village of Karterados. This cave style luxury villa offers high end amenities and facilities in indoor area and outdoor area . Near the villa only 5 minutes by foot you can find the local bus stop ,also near by you can find everything you need like restaurants,super market,coffee shops ,patisserie,the police station and the general hospital of Santorini.

Top guest favourite
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
5 out of 5 average rating, 216 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.

Guest favourite
Villa
4.94 out of 5 average rating, 103 reviews

Makrilis private relax villa

This spacious 110 sqm private villa in Karterados is ideal for families, friends, or couples seeking comfort and privacy in Santorini. It features two bedrooms, including a master bedroom, a fully equipped kitchen, large outdoor terraces, a private jacuzzi, and Aegean Sea views. Located in a quiet area with easy access to Fira, the villa offers a perfect balance of space, relaxation, and value for a comfortable island stay.

Top guest favourite
A spacious balcony features an externally heated jacuzzi, illuminated by subtle lighting. The moon casts a gentle glow over the serene sea and distant coastline, while a muted landscape is visible in the background, creating a tranquil nighttime atmosphere.
Cycladic home
4.98 out of 5 average rating, 124 reviews

Terra e Lavoro Suite with Hot Tub & Sea View

The exceptional space of Terra e Lavoro in Santorini was ideally designed to offer a personalized experience of enjoyment to those seeking a luxurious retreat on their vacation. The Terra e Lavoro luxurious apartment in Exo Gonia is a modern Villa in Santorini with traditional architecture, ready to welcome its guests and lead them to unique moments of relaxation.

Top guest favourite
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, 285 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 favourite
A serene outdoor space features a small jacuzzi surrounded by white walls and greenery. Two wooden lounge chairs with soft cushions are positioned for comfort. The bright blue sky is visible above, enhancing the tranquil setting.
Flat
4.9 out of 5 average rating, 193 reviews

Nostos Apartments Fira | Zeus

Beautiful and modern flat in the center of Fira, just 5 minutes walk from the famous cliffs of Santorini overlooking the volcano (caldera). The house is fully equiped and has a terrace with a beautiful jacuzzi. The area offers shops for all daily needs, like supermarkets, bakeries and touristic shops as well as restaurants, bars and clubs.

Popular amenities for cycladic home rentals in Santorini Caldera