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, 330 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, 392 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

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, 237 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 tranquil outdoor jacuzzi is visible, with a view of iconic blue-domed structures nearby. The sun casts a warm glow, reflecting on the water. The serene ambiance is enhanced by the surrounding landscape, suggesting a peaceful retreat in a picturesque setting.

4.99 out of 5 average rating, 162 reviews

Santo Blue Horizon Villa | Jacuzzi | Caldera View

This unique villa is located in the heart of Oia in an excellent position and has stunning views. The famous Three Domes just in front of villa with panoramic view overlooking the santorinian caldera and the aegean sea, have magnetized visitors and photographers from all over the world, making it, the most popular spot in Santorini. The villa is in perfect harmony with the natural surroundings of the area and follows the principles of traditional Cycladic architecture.

4.98 out of 5 average rating, 221 reviews

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

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, and the Ferry Port at approximately 23 km.

4.91 out of 5 average rating, 604 reviews

A bright and airy living space features a round dining table with four chairs and a decorative plate at the center. Large windows allow natural light to fill the room, revealing views of the sea and sky beyond. A cozy sofa and modern television complete the setting.

Home in Oia

Divine View Collection

Our new Private cave house is renovated in 2017 and decorated by our interior designers with great taste and elegance, relaxing colours and romantic details. It has a double bedroom with an king size, built , double bed, and a loft with a double wooden bed , a large comfortable living room with one built sofa bed and a table with four chairs . There is an LCD cable TV, Wifi, a fully equipped kitchenette and a modern bathroom with a built shower place.

4.98 out of 5 average rating, 179 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

Our brand new My Bozer twin villas are located by the sea, right at the entrance of the famous Oia village. Villa Iliada and villa Odyssey can host couples, families or group of friends, offering all necessary amenities that will guarantee a relaxed, private holidays in the most beautiful place on earth, Santorini island! You can either book one (up to 6 guests) or both villas (12 guests) if you wish to spend holidays with friends

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, 243 reviews

Bluedome Suite by Otium Villas Santorini

Luxury Cave Suite in Oia | Private Heated Jacuzzi | Sea & Caldera Views Wake up in a stylish cave suite carved from Santorini’s volcanic cliffs, just steps from Oia’s most iconic blue-domed churches and world-famous sunset spots. Designed for couples or small families who value modern comfort, traditional Cycladic charm, and panoramic views, Bluedome Suite at Otium Villas delivers a tranquil, unforgettable Santorini experience.

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

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.

4.99 out of 5 average rating, 196 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!

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.

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.

5 out of 5 average rating, 152 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

4.99 out of 5 average rating, 105 reviews

An open-air terrace features two lounge beds and a shaded cabana, offering expansive views of the tranquil Aegean Sea. The bright blue sky, dotted with fluffy clouds, contrasts beautifully against the serene water below, creating a peaceful outdoor space.

Cycladic home in Fira

Sublime Villa with sea view

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, 151 reviews

Olyra Traditional Cave Houses 2

A private hot tub is set along a glass railing, offering views of the surrounding landscape. A soft towel rests beside the water, with a straw hat adorned with a floral accent nearby. The sky is partly cloudy, suggesting a pleasant atmosphere.

4.99 out of 5 average rating, 117 reviews

Lithos Houses with private heated jacuzzi

4.83 out of 5 average rating, 160 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

An outdoor terrace is presented with a dining table surrounded by chairs, where greenery enhances the space. The walls, adorned with blue window frames, contrast with the white architecture. A staircase leads to an upper level, while a stone pathway provides access to various areas.

4.83 out of 5 average rating, 123 reviews

Villa Fekibis, jacuzzi, sea view

4.88 out of 5 average rating, 264 reviews

A scenic view is framed by an open window, showcasing the deep blue sea and distant boats. On the windowsill, a bottle of wine rests beside two glasses and a travel guide, hinting at a relaxing atmosphere and exploration.

Hotel room in Oia

mu perfect house with caldera sunset view

Cycladic home in Megalochori

A modern living area features a curved, turquoise sofa against a white wall, complemented by decorative wall hangings. A dining table is positioned nearby, adorned with fresh flowers and food items. Natural light illuminates the space, enhancing its welcoming atmosphere.

4.97 out of 5 average rating, 275 reviews

Villa Ruby

4.93 out of 5 average rating, 193 reviews

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

Radiant Santorini Standard

Cycladic house rentals with a patio

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.

4.95 out of 5 average rating, 58 reviews

Lunar Sea Suite-1BR/Hot-Tub/Sea View

4.93 out of 5 average rating, 14 reviews

A private hot tub located on a terrace offers scenic views of the surrounding white-washed buildings and the Aegean Sea. A blue-domed church is visible in the background, under a clear sky with few clouds. The setting presents a relaxing atmosphere.

Home in Pyrgos Kallistis

Thiro Exclusive Villa in Pyrgos

Cycladic home in Akrotiri

A private hot tub with bubbling water is positioned on a terrace, surrounded by white walls. In the background, a traditional bell tower rises against the clear blue sky, adding a touch of local architecture. Sun loungers are placed nearby for relaxation.

5 out of 5 average rating, 17 reviews

Spilia Cave Nicole Santorini

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

Cycladic home in Vourvoulos

4.93 out of 5 average rating, 58 reviews

Beyond Crowds Seafront Escape | Sonus Mare 2

4.86 out of 5 average rating, 36 reviews

The studio features a queen size bed, a cozy armchair, and a small wooden table. Closets with hanging space and a kitchenette equipped with a microwave and refrigerator are also visible. Soft lighting enhances the bright, airy atmosphere of the space.

Dome in Santorini

Elena Deluxe Studio (Sunny & Quiet, near Caldera)

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

Cycladic house rentals with a washer and dryer

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 !

4.65 out of 5 average rating, 112 reviews

A spacious terrace features a shaded canopy, offering a stunning view of the serene Aegean Sea. White-washed buildings and distant islands are visible under a clear blue sky, creating a tranquil backdrop for relaxation.

Apartment in Ia

Captain’s studio twin beds with sea view in Oia

4.85 out of 5 average rating, 65 reviews

A spacious terrace offers a clear view of the sea and the surrounding village. A small white table with chairs is positioned in the center, complemented by a potted flower. The warm beige walls enhance the open ambiance under a bright blue sky.

Castle in Fira

Castelli Porta - Unique castle stay with sea view

4.91 out of 5 average rating, 78 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

4.88 out of 5 average rating, 16 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

An inviting heated cave swimming pool features smooth white walls and bright blue water, with a metallic ladder providing access. Natural light filters through the archway above, creating a serene atmosphere within the private space.

4.89 out of 5 average rating, 61 reviews

Exclusive Villa with Outdoor Heated Pool