Cycladic house vacation rentals in Oia

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.

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

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.

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

4.99 out of 5 average rating, 206 reviews

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

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.

4.97 out of 5 average rating, 294 reviews

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 in Oia

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.

Cycladic home in Santorini

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.

4.99 out of 5 average rating, 224 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!

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.

4.96 out of 5 average rating, 241 reviews

Bluedome Suite by Otium Villas & Suites

Bluedome suite is a renovated traditional cavehouse ideal for couples and small families. It has been built with the traditional Cycladic cavehouse architecture, carved in the Volcanic caldera rock. Its’ minimally designed spaces invite relaxation and comfort. The master bedroom (with en suite bathroom) is at the back of the cave connected to the living room and seating area, kitchen and second full bathroom, overlooking the patio and custom-built hot tub.

Cycladic home in Akrotiri

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.

5 out of 5 average rating, 216 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.

A private outdoor jacuzzi is featured, surrounded by white-washed walls and a clear blue sky. Two blue-domed structures rise in the background, providing a scenic view. The bubbling water of the jacuzzi creates a relaxing atmosphere, complemented by soft lounge seating nearby.

4.99 out of 5 average rating, 154 reviews

Santo blue horizon (Blue Domes view)

The villa is located in the heart of Oia in an excellent position and has stunning views. The three domes just in front of villa with panoramic view, have magnetized visitors and photographers from all over the world, making it, the most popular spot in Santorini. The hotel is in perfect harmony with the natural surroundings of the area and follows the principles of traditional Cycladic architecture.

4.89 out of 5 average rating, 129 reviews

The private terrace features a heated pool with crystal-clear water, overlooking a panoramic ocean view. Nearby, sun chairs are positioned to enjoy the scenery. Whitewashed walls and natural stone elements enhance the serene ambiance of the outdoor space.

Dome in Oia

Deluxe Villa with outdoor Jetted Tub & Sea View

Villa Paride is the luxury honeymoon suite, with private balcony and breath taking caldera-volcano view! Can accommodate till 2 persons. Totally renovated on 2019, with king size bed, new fully equipped kitchen, new bathroom with shower. Balcony with breath taking ocean-caldera-volcano view! Terrace with sun chairs, outdoor private heated pool / jet tube, umbrellas. FREE fast WI-FI

A private terrace features potted plants against a backdrop of the caldera and sea. A plunge pool is visible, with steps leading away toward the water. In the distance, a wooden boat floats peacefully on the calm blue water.

4.99 out of 5 average rating, 192 reviews

By the Mill, Caldera, Oia

100 sq meters of traditional cave house - 3 bedrooms and 3 bathrooms, spread over 3 levels of 100 square meters of private terraces and private plunge pool. At Oia's heart - incredible volcano, caldera & sunset views all year round. Easy access, and remarkable privacy, as well as daily housekeeping and plunge pool maintenance.... By the Mill is your dream Santorini home!

4.95 out of 5 average rating, 194 reviews

A sunlit terrace overlooks the sparkling sea, featuring a hot tub and a red dining table surrounded by black chairs. Sun loungers are positioned along the edge, with the volcanic cliffs and distant islands visible in the background.

Cave in Oia

Satori Caves by Thireon

Welcome to Satori Caves - where the glittering sea meets the endless sky at the top of Oia’s breathtaking volcanic cliffs. The house has an amazing terrace with hot tub for your own private volcano viewing spot! There are a few steps to climb to reach this caldera home rewarding you with PRIVACY and away of the crowds. Managed by Thireon Houses

5 out of 5 average rating, 150 reviews

Two wooden lounge chairs are positioned on a concrete terrace, offering unobstructed views of the caldera. Two lanterns with flickering candles provide ambient lighting as the sun sets over the water, creating a serene space for relaxation.

Villa in Oia

Loukia House

Loukia House is a traditional Cycladic cave house carved inside the Oia cliff. The beautiful arched ceilings stretch along the indoor and outdoor space. Its unique location offers panoramic views of the whole island and the caldera. A relaxing terrace gives a sense of privacy in the most sought-after spot in Santorini.

Popular amenities for Oia cycladic house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly cycladic house rentals

Cycladic home in Imerovigli

A bright living space features a comfortable sofa, a round coffee table, and a dining area with a light-colored table and chairs. Large windows offer views of the sea, while steps lead to an upper level. Natural light illuminates the area, enhancing the relaxing atmosphere.

4.92 out of 5 average rating, 145 reviews

Anatoli Beach House

4.86 out of 5 average rating, 159 reviews

A wooden table is set on a balcony, featuring a bottle of rosé wine alongside two glasses. A small potted plant adds a touch of greenery, while the expansive view of the Aegean Sea and clear blue sky enhances the serene atmosphere.

Condo in Fira

So close to caldera cliff ,Sea view studio No3

4.98 out of 5 average rating, 171 reviews

A modern villa is presented with a distinctive white dome roof, surrounded by greenery and blue sea views. A shaded patio features sun loungers beside a small swimming pool, providing a relaxing outdoor space. The bright blue doors complement the serene landscape.

Dome in Oia

MyBoZer Twins Odyssey Heated private pool

4.92 out of 5 average rating, 367 reviews

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

Soundscape - cave suite panoramic sea views

Cycladic home in Pyrgos Kallistis

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.

4.96 out of 5 average rating, 149 reviews

Olyra Traditional Cave Houses 2

4.99 out of 5 average rating, 102 reviews

A bright interior space is depicted, featuring a cozy sitting area with a striped bench adorned with yellow pillows. A rustic table and white chairs sit alongside a wall mirror, while large windows offer scenic views of the sea, enhancing the light-filled space.

Cycladic home in Fira

Seaside house with mediterranean garden + sunbeds

4.98 out of 5 average rating, 226 reviews

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 Fira

Sol

4.84 out of 5 average rating, 138 reviews

A clean outdoor patio area features a small table set with a tablecloth, surrounded by two wooden chairs with pink cushions. Whitewashed walls and windows with shutter-style openings create a bright and inviting space under a clear blue sky.

Apartment in Fira

Souita Mantilaria

Cycladic house rentals with a patio

4.95 out of 5 average rating, 55 reviews

A private terrace is presented with a cozy seating area, featuring plush cushions in neutral tones. A small table holds a bottle of wine and two glasses, alongside a pineapple. The backdrop showcases a tranquil sea view during sunset, with soft hues in the sky.

Home in Oia

Lunar Sea Suite with Hot-tub and caldera view

A cozy living area features a comfortable seating nook with a stone-gray couch and a small table. Light pours in from the open doors leading to a balcony, where two chairs and a table overlook the outdoor scenery. A television is positioned for easy viewing.

Cycladic home in Fira

4.74 out of 5 average rating, 68 reviews

Aeron Suite Villa w. Queen Bed Sea & Mountain View

Cycladic home in Megalochori

A modern villa is set against a clear blue sky, featuring a spacious pool surrounded by wooden lounge chairs. The property includes multiple structures with white exteriors, accentuated by lush landscaping and steps leading to a peaceful outdoor area.

5 out of 5 average rating, 3 reviews

Apelia Santorini Holiday Villa with Pool and View

4.92 out of 5 average rating, 13 reviews

An outdoor patio area is visible, featuring wooden dining furniture under a shaded structure. Soft lighting enhances the space as it transitions into evening. Steps lead down to an entrance framed by stone walls, surrounded by greenery and palm trees in the background.

Home in Mesaria

Euphemus Cave House

A comfortable outdoor seating area features a sunlit couch adorned with various patterned cushions. A rustic wooden coffee table is positioned in front, complemented by natural decorative elements and overhead bamboo shades that add texture to the space.

Cycladic home in Chora

4.67 out of 5 average rating, 24 reviews

L ´Apothiki

Cycladic home in Vourvoulos

A private terrace features a hot tub surrounded by sun loungers, with a view of the distant sea and rocky landscape. A palm tree adds a tropical touch, while a comfortable seating area is situated nearby, offering a serene outdoor space for relaxation.

4.93 out of 5 average rating, 57 reviews

Beyond Crowds Seafront Escape | Sonus Mare 2

4.93 out of 5 average rating, 70 reviews

A private Jacuzzi filled with clear water is featured in a sunlit outdoor space. Two stylish black chairs are positioned nearby, with a bottle of wine placed on the edge of the tub. The smooth white walls are complemented by large windows, allowing for light to enter.

Condo in Kamari

Nostos Apartments Kamari | Calypso

A stunning terrace is shown featuring a hot tub and a sun lounger under a wide-brimmed umbrella. A coastal view is visible in the background, showcasing the blue sea and clear sky. Refreshments are placed on a small table beside the lounger.

Private room in Vourvoulos

5 out of 5 average rating, 3 reviews

360 View Suite with Private Jacuzzi

Cycladic house rentals with a washer and dryer

An outdoor area features a private pool surrounded by sun loungers and a large dining table. Soft lighting illuminates the space, enhancing the tranquil atmosphere. Nearby, a shaded area is provided by a large umbrella, while traditional architecture forms the backdrop.

Home in Akrotiri

4.5 out of 5 average rating, 4 reviews

Boutique Villa prive pool, breakfast Akrotiri

Home in Exo Gialos Karteradou

A relaxing moment by the private pool is captured, featuring clear blue water and a scenic view of the sea. A seated figure holds a glass of drink near an ice bucket, suggesting a tranquil atmosphere for leisure.

4.96 out of 5 average rating, 26 reviews

"Sand" sea view luxury villa with pool by beach !

4.94 out of 5 average rating, 72 reviews

An outdoor jetted tub is highlighted with clear blue water, overlooking the Aegean Sea. The vibrant blue sky complements the scenic backdrop of white buildings and a windmill in the distance, creating a peaceful and inviting atmosphere.

Windmill in Oia

The Sunset Windmill

The property showcases a modern villa illuminated at dusk, featuring spacious lounge chairs by a tranquil pool. The serene mirrored water reflects the villa's elegant architecture, with soft lighting highlighting the entrance and surrounding greenery.

Cycladic home in Megalochori

4.88 out of 5 average rating, 41 reviews

Samsara - Santorini Luxury Retreat

4.87 out of 5 average rating, 15 reviews

An inviting pool area features a gently curving pool surrounded by stone tiles. Sun loungers are placed alongside the water, and lush greenery is visible in the background. The evening sky and illuminated landscaping create a tranquil atmosphere suitable for relaxation.

Dome in Kamari

Felicity Villas Santorini - Victoria

Apartment in Pyrgos Kallistis

A private hot tub is set in a bright, airy space with views of the sea and sky. Soft waves can be seen in the distance. Sunlight fills the room, highlighting the clean lines of the architecture and the serene atmosphere.

4.83 out of 5 average rating, 40 reviews

Genesis Suite with Caldera View and Hot Tub

4.7 out of 5 average rating, 148 reviews

A panoramic view showcases the caldera of Santorini, complemented by a serene blue sea. A white-washed church stands nearby, framed by the iconic architecture of Oia. Gentle clouds float in a clear sky, enhancing the tranquil atmosphere of the landscape.

Apartment in Santorini

Captain's Economy Studio with sea view in oia