Cycladic house holiday rentals in Oia

4.96 out of 5 average rating, 111 reviews

An open-plan living area featuring textured stone walls and a high arched ceiling. A wooden dining table is surrounded by chairs, with a modern kitchen visible in the background. A cozy seating area offers comfortable sofas, while a small plunge pool is nestled in one corner.

Earthen home

Canava Villas II - Heated Pool - Santorini

Villa#2 comes in 2 level floors and accommodates up to 6 people. On the ground floor there is a master bedroom, bathroom, fully equipped kitchen, lounge and WC. The upper floor provides 4 single floor mattresses or 2 double ones & its own bathroom. Outdoor private pool with Jacuzzi, patio, dinning area and sun lounges! Welcome drinks, basket of seasonal products, Nespresso coffee, Concierge services, A/C, Netflix, daily housekeeping, laundry services and many more amenities are waiting for you!

4.99 out of 5 average rating, 221 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

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.

4.99 out of 5 average rating, 164 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.

4.88 out of 5 average rating, 262 reviews

Bluedome Cavehouse by Otium Villas Santorini

Luxury Cavehouse in Oia | Caldera Views | Heated Jacuzzi | Sleeps up to 6 Wake up to breathtaking caldera and Aegean Sea views from the private terrace of Bluedome Cavehouse, a spacious luxury cave villa in the heart of Oia, Santorini. Blending authentic Cycladic architecture with modern comfort and design, this beautifully renovated cavehouse offers an unforgettable retreat for couples, families, and small groups seeking romance, privacy, and panoramic sunsets.

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.

5 out of 5 average rating, 218 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.

4.94 out of 5 average rating, 164 reviews

A panoramic view showcases the deep blue Aegean Sea against a clear sky. The coastline features unique rock formations, while white-washed buildings with blue accents dot the hillside, creating a serene landscape. A sailboat is visible in the distance, adding to the tranquil ambiance.

Cave

Mystic suite with outdoor jacuzzi and caldera view

With the success of Kaleidoscope Cave Houses, Kaleidoscope Oia Suites soon followed. The Mystic Suite with hot tub and caldera view, carved into the unique caldera cliffs is a fully renovated suite which is located in Oia's center and very close to the famous BLUE DOMES of Oia with breathtaking views over the caldera, the volcano and the Aegean Sea. The other listing is the Blue Dome suite with private rooftop and jacuzzi.

4.99 out of 5 average rating, 198 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!

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.

4.98 out of 5 average rating, 132 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.

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

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.

4.96 out of 5 average rating, 237 reviews

Quiet White Studio

Quiet White Studio is a small but cosy studio in the village of Oia, hanging on the cliff of the caldera. It is located about 85 steps below Oia's main walking path, practically 4 minutes on foot from Oia's center. The studio is good for couples and solo adventurers.

A panoramic view captures the deep blue sea contrasting with the rugged cliff, dotted with white buildings and blue-domed roofs. A cruise ship glides smoothly across the water, while the picturesque landscape of the caldera extends toward the horizon.

4.92 out of 5 average rating, 401 reviews

VILLA MATILDE-VOLCANO VIEW

VILLA MATILDE in Santorini sits on the edge of the Caldera in Oia.A charming Cycladic house, with typical domed roofs and high ceilings, VILLA MATILDE is spacious enough to accommodate 6 or 7 people.2 bedrooms, sofa beds at the living room,2 showers

A balcony offers an expansive view of the sea and nearby cliffs, with vibrant townhouses in the background. A round table is set with a bottle of wine, glasses, and a bowl of snacks. A comfortable chair is positioned nearby, inviting relaxation.

4.93 out of 5 average rating, 347 reviews

Pano Meria Venetian Style Studio II

This property is half of a Venetian era Captain House. Centrally located in the heart of Oia but protected by an interior courtyard. It has wooden floors, and traditionally built high ceilings. It fits up to 4 persons. Perfect views of the caldera.

Popular amenities for cycladic home rentals in Oia

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly cycladic home rentals

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.

4.98 out of 5 average rating, 107 reviews

Sublime Villa with sea view

4.87 out of 5 average rating, 209 reviews

A private terrace features a shimmering pool with views of the sea and the caldera. Whitewashed buildings in Oia line the cliffside under a clear blue sky, creating a serene backdrop for relaxation.

Villa

Top Caldera view villa with Hot Tub in Oia

An outdoor seating area is featured under a wooden pergola, providing shade and comfort. Two orange chairs are placed near a small table, surrounded by vibrant flowers and greenery. The entrance to the home is visible through a large glass door, complemented by a nearby window.

4.9 out of 5 average rating, 104 reviews

Absolute peace south villa a place to chill

A serene outdoor space is highlighted, featuring sun loungers positioned by a swimming pool. The horizon glows with hues of orange and yellow as the sun sets, while a hanging chair gently sways nearby. Natural stone elements frame the view, adding texture to the scene.

4.98 out of 5 average rating, 211 reviews

Saints Apostles Villa with private pool

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.

4.84 out of 5 average rating, 170 reviews

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

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, 279 reviews

Villa Ruby

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.

4.98 out of 5 average rating, 129 reviews

Barocco Bello Villa

Cycladic home 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, 59 reviews

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

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

4.93 out of 5 average rating, 15 reviews

Thiro Exclusive Villa in Pyrgos

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

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, 61 reviews

Seafront Retreat with Large Veranda | Sonus Mare 2

4.93 out of 5 average rating, 75 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.

Apartment

Nostos Apartments Kamari | Calypso

4.86 out of 5 average rating, 37 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

Elena Deluxe Studio (Sunny & cozy, near Caldera)

Two wooden lounge chairs with navy cushions are positioned beside a clear, inviting hot tub. The surrounding area features a smooth concrete surface, bathed in natural sunlight, accentuating a serene outdoor setting.

4.92 out of 5 average rating, 86 reviews

Casa Bu 4 - 1Bedroom Apartment with Prive Hot-Tub

Cycladic home rentals with a washing machine and dryer

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 !

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.

4.66 out of 5 average rating, 114 reviews

Captain’s studio twin beds with sea view in Oia

4.85 out of 5 average rating, 65 reviews

The exterior of a traditional Venetian house from the 15th century is shown, featuring a blend of light-colored stucco walls. Windows with wooden frames are visible, and the architecture highlights the structure's historical significance. A clear blue sky serves as a backdrop.

Castle

Castelli Porta - Unique castle stay with sea view

4.91 out of 5 average rating, 79 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

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

Felicity Villas Santorini - Victoria

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, 62 reviews

Exclusive Villa with Outdoor Heated Pool

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.