Waterfront holiday rentals in Oia

A scenic view from HELIOS Cave House shows a guest overlooking the caldera and the sea. Whitewashed buildings line the hillside, accentuated by the brilliant blue sky. The image captures the serene atmosphere that surrounds the property, inviting relaxation and tranquility.

4.91 out of 5 average rating, 189 reviews

SantoriniParadise: HELIOS cave house, sunset view!

HELIOS Cave house is a roomy, well-lit, romantic love nest! In the heart of old Oia, it offers an unobstructed view of Oia's famous sunsets! That is why SISTERHOOD OF THE TRAVELLING PANTS was filmed just there! It features 2 double beds, a sofa bed, a corner sofa & a red stylish bathtub. There is a little, cozy yard and from SANTORINI PARADISE HOUSES' private rooftop you enjoy amazing sunsets & the Ammoudi port. Jacuzzi for 3 persons is available on Tuesday, Thursday & Saturday, just 2 min away

4.95 out of 5 average rating, 179 reviews

A clear view of the sea is framed by two arched windows, displaying the tranquil water and sun loungers on a stone patio. The interior features light-colored walls and wooden shutters, enhancing the open and airy feel of the space.

Cave in Red beach

Cueva del Pescador

Enjoy two luxurious, newly-remodeled cave dwellings only two meters from the sea: Cueva de olas and Cueva del pescador! These gorgeous spaces are perfect for discerning honeymooners, couples, or anyone who wants to take a break from the real world -- and from the typical tourist traffic of Santorini. Cueva de olas was originally the residence of a local fisherman; Cueva del pescador was his boat-house. Traditional decor and outstanding hospitably complete this perfect, unique rentals!

Cycladic home in Pori Beach

A sunlit terrace showcases a relaxed seating area with colorful cushions and a hanging swing chair. Potted flowers line the walls, and a light green door leads to the interior. The expansive sea view is unobstructed, adding a serene backdrop to the outdoor space.

4.88 out of 5 average rating, 147 reviews

Window towards Sunrise - Loft house

Welcome dear traveler to the Window towards Sunrise! It is one of the houses in Cybele Holistic Space located between Fira and Oia and is situated just one minute walking distance from Pori beach, where you can easily enjoy a swim any time you want. It consists of two floors and from the upper floor you can literally enjoy the sunrise, if an early bird! The house has been renovated very recently, combining traditional cycladic architecture with our personal designs and love !

4.88 out of 5 average rating, 112 reviews

A private heated plunge pool with clear blue water is situated on a terrace overlooking the ocean. A sun umbrella provides shade, while white stones outline the pool. The surrounding cliffside views showcase the sea and distant landforms, enhancing the serene setting.

Cave in Oia

The Blue Domes Cave House by Spitia Santorini

Experience the iconic beauty of Santorini at The Blue Domes Cave House, a truly enchanting and luxuriously appointed home perfectly situated in the heart of Oia. Directly facing the world-famous blue domes, offers an unrivalled vantage point for breathtaking caldera views and mesmerising sunsets from its private outdoor plunge pool. Ideal for a romantic escape or a small family, accommodating up to 5 guests, it embodies the magic of Santorini with its unique charm and prime location.

A tranquil outdoor area features a custom hot tub accompanied by two lounge chairs. A panoramic view of the blue sea and cliffs is visible, complemented by iconic blue-domed buildings in the background. The scene is well-lit under clear blue skies.

4.87 out of 5 average rating, 253 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.

Cycladic home in Imerovigli

An outdoor terrace features multiple lounge areas with sunbeds and a dining table set for breakfast. Soft cushions and towels are arranged neatly, while a breathtaking view of the Aegean Sea and volcanic island is visible in the background.

4.92 out of 5 average rating, 276 reviews

Chess House - Santorini Traditional Home

My place is a traditional Santorini home! Built on the Caldera (Cliff), into the rock, where families of the people of the sea would live, always looking out to the Aegean where their loved ones made their living.. You’ll love my place because of the impeccable view, the peace and quiet, the traditional home experience which is so rare these days.. My place is good for one or two couples or families with or without kids. Reserved parking for guests is included.

4.99 out of 5 average rating, 134 reviews

A private terrace displays a round table set against the backdrop of a striking sea view, with the village of Oia perched on the cliffs. A palm tree shades the area, while vibrant turquoise accents complement the whitewashed walls and surrounding greenery.

Cave in Oia

Boutique Cave Suite in the heart of Oia

Perched on the cliffs of the scenic village of Oia, Blessed Blue is a newly renovated 200-year-old boutique cave suite offering stunning caldera views of the endless Aegean Sea and sky. It features a kitchenette, a living room area with two sofa beds, and a bedroom. The bathroom has a mounted rain shower as well as a handheld unit, a hairdryer, bath products and bath towels available to guests. Other amenities include Wifi, air conditioning, WC, and safe.

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.

4.89 out of 5 average rating, 241 reviews

A serene outdoor seating area is nestled next to a private whirlpool, surrounded by whitewashed walls. Decorative elements include a potted cactus and vibrant pink flowers, adding a touch of colour. The space is bathed in natural light from the clear blue sky above.

Cave in Ia

White Cellar Cave Houses by Cycladica

The two separate, white washed cave houses are carved in the mountain in the heart of Oia, right on top of the stairs that lead to Armeni bay, connected with outdoor stairs. They are newly renovated with respect to the local building crafts and the typical Santorini architecture. They offer the classical Cycladic beauty of being simple while homey and welcoming.

4.99 out of 5 average rating, 208 reviews

An outdoor seating area features wooden lounge chairs positioned to face the ocean, capturing a sunset view. A dining table is visible in the background. Lanterns are placed on the ground, and trees provide a natural frame against the colorful sky.

Villa in Imerovigli

Villa Aronia

This immaculate, 80 m^2 and fully equipped Villa invites comfort and tranquility. Highlights include breathtaking view, secluded beach, only 20 meters away, spacious garden setting for relaxing and entertaining and private parking. Perfect for anyone, this home is ideally positioned to enjoy all year round in Santorini.

A scenic view showcases traditional Cycladic architecture with whitewashed structures and striking blue domes. In the foreground, a quiet outdoor space features a small table set with fruit, while the expansive Aegean Sea and volcanic caldera are visible in the background under a clear blue sky.

4.97 out of 5 average rating, 128 reviews

Evmenia Luxury Cave Villa

Evmenia Luxury Cave Villa is a spacious (75 sq. m.) self-catered home located right in the heart of the traditional settlement of Oia. The villa has a (25 sq. m.) private patio which offers an unobstructed, gorgeous, panoramic view of the magnificent Caldera and the unique crystal clear waters of the Aegean Sea.

4.94 out of 5 average rating, 122 reviews

A heated jacuzzi features glowing blue water, framed by a wooden deck. Nearby, an outdoor dining area with a table and chairs is positioned under a shaded pergola. The expansive view includes the tranquil sea and distant hills, illuminated by the evening sky.

Villa in Akrotiri

Premium Two Bedroom Villa with Jacuzzi & Sea View

The Premium Villa exudes a vintage charm with its unique architectural features and traditional design elements. The whitewashed walls and rustic tones create a warm and inviting atmosphere, while the vintage furnishings add to the overall character and authenticity of the space.

Popular amenities for Oia waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

5 out of 5 average rating, 22 reviews

Apartment in Karterádos

Aquarill

4.87 out of 5 average rating, 119 reviews

An outdoor terrace offers stunning views of the caldera and neighboring island. A modern white chair sits beside a small table, with a person relaxing and reading. Two jacuzzis are visible, and the clear blue sea stretches into the horizon.

Apartment in Imerovigli

Olia Dome, 2 bedrooms, 2 jacuzzis and volcano view

A modern villa is set against the backdrop of an olive grove, showcasing a blend of natural stone and contemporary architecture. Large windows reflect soft lighting, illuminating the spacious interiors. The structure's design emphasizes openness while integrating harmoniously with the surrounding landscape.

Apartment in Akrotiri

Unique Castle in The Hilltop

Apartment in Paralia Perivolos

4.72 out of 5 average rating, 102 reviews

'Thalassitis' coastal apartment 1

4.88 out of 5 average rating, 17 reviews

A clear view of a private infinity pool is showcased in front of a modern white building. Adjacent to the pool, two wooden chairs are positioned on a tiled patio, with arched doorways leading into the interior spaces.

Apartment in Vothonas

Amphitrite Suite 2 (private pool)

A private outdoor heated Jacuzzi is situated under a shaded area, offering views of the Aegean Sea. The water's surface reflects the sky, with lounge chairs visible in the distance, creating a serene atmosphere for relaxation.

Apartment in Oia

Almyra Deluxe Suite with Sea View & Jetted tub

4.95 out of 5 average rating, 185 reviews

Apartment in Fira

Yposkafo Suites - Private Studio - Santorini

4.87 out of 5 average rating, 52 reviews

A wooden lounge chair is positioned beside a serene plunge pool, offering a view of a gradient sunset sky filled with warm hues. The calm water reflects the colors, creating a tranquil atmosphere.

Apartment in Oia

Deluxe Suite Sea View & Plunge Pool @Aplada Suites

Waterfront house rentals

4.87 out of 5 average rating, 31 reviews

A modern exterior features a covered terrace with light wood furniture and a pool. The vibrant blue sky is visible, along with lush landscaping and warm sunlight creating a serene ambiance. Comfortable seating arrangements invite relaxation near the pool.

Home in Santorini

Beach front Villa Pasithea @home by the sea

A cozy sleeping area features a spacious bed adorned with neutral-colored linens. Natural light enters from the glass doors, which open to a garden view. Two towels are neatly placed on the bed, complemented by minimalistic shelving and soft lighting fixtures.

Home in Kamari

4.38 out of 5 average rating, 8 reviews

E&E small villa Santorini Kamari

A traditional summer house is showcased against a clear blue sky, framed by a lush green landscape. The two-level structure features a warm terracotta exterior, multiple large windows, and a welcoming entrance flanked by outdoor seating areas.

Home in Baxedes - Oia

4.83 out of 5 average rating, 65 reviews

Summer House in Santorini

A dining table is set outdoors, accompanied by wooden chairs and adorned with colorful drinks and fresh fruits. A well-maintained garden area features a palm tree, while a white building with blue accents is visible in the background.

Home in Santorini

4.57 out of 5 average rating, 7 reviews

Blue Heaven Villa 33 Peaceful Santorini sea house

5 out of 5 average rating, 9 reviews

A sunlit terrace features a comfortable lounge chair beside a dining area equipped with a table and chairs. The backdrop consists of a scenic mountain landscape, with greenery accenting the space. The overall ambiance suggests a relaxing outdoor environment for guests.

Home in Perissa

DP Homes Beachside in Santorini

An open interior space is visible, showcasing a kitchen with modern appliances and light wood cabinetry. A dining table with white chairs is positioned nearby, adjacent to a blue sofa. Natural light enters through large windows, highlighting the rustic stone ceiling and tiled floor.

Home in Vourvoulos

4.8 out of 5 average rating, 76 reviews

Go Plaza Houses 1

An open-air terrace features a private hot tub with panoramic views of the caldera and ocean. Minimalist outdoor furniture, including two sun loungers and a side table, provide relaxation space. A person enjoys a drink while seated nearby, framed by the stunning landscape.

Home in Imerovigli

Santorini 2 BDR Villa With Outdoor Jacuzzi & Views

5 out of 5 average rating, 16 reviews

An open living area features a kitchenette equipped with a refrigerator and microwave, alongside a dining table with four chairs. Soft lighting highlights the warm, earthy tones of the furnishings. A staircase leads to additional spaces, while a decorative rug adds texture to the tiled floor.

Home in Vlichada

Unique place Pool & Beach

Other waterfront holiday rentals

4.75 out of 5 average rating, 109 reviews

A serene outdoor space features two lounge chairs positioned beside a private pool. The scene is enhanced by a stunning sunset over the ocean, casting warm hues across the sky. A wrought-iron railing provides an elegant border to the breathtaking view.

Villa in Fira

Villa Dakoronia•Stunning caldera view Private Pool

Cycladic home in Santorini

A private jacuzzi overlooks the serene coastline, with the deep blue sea in the distance. Two cocktails are placed on the edge of the spa, inviting relaxation amidst a peaceful setting. The surrounding landscape features hills and traditional white houses.

4.88 out of 5 average rating, 75 reviews

Aerno, B&B cave house at Arvanitis Village

A cozy outdoor terrace features a wooden dining table surrounded by folding chairs. A built-in barbecue station is visible, along with a shaded area created by a wooden pergola. Bright sunlight illuminates the space, enhancing the inviting atmosphere of the surrounding greenery.

5 out of 5 average rating, 12 reviews

Uva Nera House Oia

Cycladic home in Firostefani

4.95 out of 5 average rating, 86 reviews

Spiti Barbara | Cave with Caldera View & Jacuzzi

Holiday home in Ormos Ammoudiou

A bright and airy bedroom features a spacious bed dressed in crisp linens, accompanied by a soft blue blanket. Natural light filters through a large window with yellow frames, illuminating the room's smooth white walls. A textured round rug lies underfoot, adding warmth to the minimalist decor.

4.93 out of 5 average rating, 72 reviews

Anelia House

4.99 out of 5 average rating, 81 reviews

A modern living space features a large window offering a clear view of the sea, allowing abundant natural light to fill the room. A wooden dining table with four chairs is positioned alongside a comfortable sofa adorned with soft cushions. Minimalist decor enhances the serene atmosphere.

Villa in Kamari

Kamara Sea View Superior Suite

4.96 out of 5 average rating, 89 reviews

An outdoor seating area features a white table and chairs, overlooking the deep blue Aegean Sea and volcanic islands. A guest is comfortably seated, enjoying the view under the clear sky. The terrace showcases smooth white surfaces, enhancing the serene atmosphere.

Cycladic home in Fira

Gitsa Cliff Luxury Villa, Volcano View, Jacuzzi