Cycladic house holiday 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, 322 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

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

mu perfect house with caldera sunset view

Really a authentic cavehouse on caldera with unique view, around has only white cavehouses. the house isin oia village, on caldera. is ideal for honeymoon and relax holidays.the house is private, has a private patio with table and chairs. has seaview and from inside! around has the best restaurants and many shops , travel ofices and gallerys, also you can to rent car or moto. the house has aircontition and free wifi. also we provide towels and sheets and bathroom amenities. MHTE1167K050B0902201

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, 383 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

A private veranda features an outdoor heated jacuzzi pool alongside comfortable seating. The serene view encompasses the caldera and the Aegean Sea, framed by clear blue skies dotted with clouds, creating an atmosphere of tranquility.

4.92 out of 5 average rating, 237 reviews

Apanema Cavehouse by Otium Villas Santorini

Luxury Cave Villa in Oia | Private Jacuzzi | Caldera Views Experience a refined luxury retreat designed for space and serenity. Perched high on the Oia cliffs, this authentic cavehouse offers an airy, elevated perspective of the Caldera and Aegean Sea. Highlights: Ultimate Privacy: Unobstructed views from your private veranda. Leisure: Custom heated Jacuzzi & stylish lounge area. The Space: King-size master bedroom, spacious living area, and kitchenette. Historic charm meets modern calm.

A tranquil private jacuzzi provides a relaxing space for guests, framed by vibrant pink flowers. In the background, the caldera and sunset create a serene landscape, highlighting the scenic views of the surrounding hills and sea.

4.88 out of 5 average rating, 112 reviews

Deluxe Suite with External Jacuzzi,Caldera View

Deluxe Suite of 30 sqm-extrenal private jacuzzi. It has a double built-in bed, bathroom with shower and all the comforts ensure quality living conditions.Has view of the caldera,sunset and the volcano is a reference point for each guest.The 3 Luxury suites of La Casa De Caldera are on the same level.The yard of La Casa De Caldera is divided by dividers,into 3 pieces,each piece corresponding to each suite and every suite includes private sunbeds, private jacuzzi,private umbrella.

4.98 out of 5 average rating, 218 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

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, 589 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

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.

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.

A serene terrace features comfortable seating beside a clear hydromassage pool. The smooth surface of the water reflects the soft colors of the sky, while gentle waves can be seen lapping at the shoreline in the distance.

4.89 out of 5 average rating, 173 reviews

Michelangelo Beach Villa with Sea View

Michelangelo Beach Villa is a perfect getaway destination for those seeking contact with nature and peace of mind. The villa is decorated in respect to the island's tradition, in pastel colors so our guests can take in as much of nature's and sea's beauty as they can. The fresh water hydromassage is not operating during December, January and February.

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.

4.87 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

This charming, spacious villa sits at the highest point of the village, offering stunning, unobstructed views of the famous Caldera and the volcano. With a king-size bed and a private balcony featuring a hot tub, it promises unforgettable moments of relaxation and pure enjoyment.

4.93 out of 5 average rating, 339 reviews

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.

Home

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

4.93 out of 5 average rating, 114 reviews

Sea & Sun | Beachfront Luxury - Full Sea View

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.

4.99 out of 5 average rating, 103 reviews

Sublime Villa with sea view

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

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, 206 reviews

Saints Apostles Villa with private pool

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.

4.98 out of 5 average rating, 227 reviews

Sol

4.92 out of 5 average rating, 224 reviews

Simplicity Two Storey Suite (Sea View) 35 m²

The outdoor area features whitewashed walls adorned with climbing vines. A doorway leads into a bright interior space, with natural light filtering through. A small table and chairs are positioned under a sun umbrella, creating a cozy spot for relaxation.

4.79 out of 5 average rating, 151 reviews

House of the Singing Birds.

A spacious terrace offers panoramic views of the sea and nearby islands. Colorful chairs surround a round table, where drinks and snacks are lightly arranged. A person in a summer outfit gazes out at the landscape, framed by the vibrant colors of the furniture.

4.98 out of 5 average rating, 126 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, 57 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, 16 reviews

Spilia Cave Nicole Santorini

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.

4.74 out of 5 average rating, 68 reviews

Aeron Suite Villa w. Queen Bed Sea & Mountain View

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 spacious outdoor dining area is set against a clear blue sea, featuring a wooden table surrounded by white woven chairs. Sunlight creates a bright atmosphere, with a shade sail overhead providing comfort. Scenic views of the coastline and mountains are visible in the background.

4.88 out of 5 average rating, 8 reviews

Petinos Traditional House

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

Euphemus Cave House

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, 58 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.

Apartment

Nostos Apartments Kamari | Calypso

Cycladic home rentals with a washing machine and dryer

The suite features a spacious bed with neatly arranged linens, complemented by a wardrobe and a television. French doors open to a private terrace with outdoor seating, offering views of the sea and surrounding landscape. Soft lighting fixtures enhance the contemporary decor.

4.83 out of 5 average rating, 12 reviews

Leto Suite with Caldera View

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.

4.65 out of 5 average rating, 112 reviews

Captain’s studio twin beds with sea view in Oia

4.91 out of 5 average rating, 75 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

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

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

A light-filled living area features large open windows providing views of the ocean. A minimalist sofa offers ample seating, complemented by natural wooden accents in the ceiling. A simple wooden desk with a chair is situated against the wall, enhancing the modern design.

4.94 out of 5 average rating, 97 reviews

Airth Suite (jacuzzi and sunset view)

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.