Waterfront vacation 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, 188 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!

A serene interior space features a light-colored plaster finish and a half-moon shaped indoor jacuzzi. A comfortable seating area with soft gray cushions provides a relaxing spot. Large arched windows frame views of the sea, allowing natural light to enhance the atmosphere.

4.84 out of 5 average rating, 259 reviews

Marble Sun Villa with Hot-Tub and Caldera View

Discover the essence of Santorini luxury at Marble Sun Villa. Set along the iconic cliffs of Oia, the villa offers breathtaking, uninterrupted views of the Caldera. Cozy cave-style bedrooms, spacious terraces, and a private hot tub create the perfect setting for pure relaxation. With warm, attentive hospitality and a prime location just steps from Oia’s vibrant pathways, Marble Sun Villa promises an unforgettable escape. Immerse yourself in the magic of Santorini at Marble Sun Villa.

4.85 out of 5 average rating, 157 reviews

An outdoor seating area is adorned with a wooden bench, decorated with colorful cushions, and a low table. A hammock is suspended nearby, providing a serene spot for relaxation. The setting boasts a coastal view at sunset, enhancing the sense of tranquility.

Home in Santorini, Thera

Wine Cellar Sunrise house

Little Wine Cellar was literally used years before, for storing delicious local wine! We rebuild it, restored it, decorated it with love and a lot of personal work .....and here it is for you to enjoy it! The studio is located just above Pori beach and iit is part of Cybele Holistic Space. It is small and sweet, yet very well equipped! As the house is located between Fira and Oia a car/scooter is definitely needed in order to move around and also explore more unique places!

4.95 out of 5 average rating, 386 reviews

A private plunge pool is showcased beneath a bright blue sky, with expansive views of the shimmering sea and distant islands. Lush greenery and a cactus are visible near the pool, adding natural elements to the serene outdoor space.

Cave in Oia

Sunset Cave House by Spitia Santorini

Embrace the quintessential Santorini experience at the Sunset Cave House, a magical retreat carved into the volcanic rock of Oia's caldera cliff. This traditional yet luxuriously appointed accommodation offers unparalleled panoramic views of the Aegean Sea and the world-famous Oia sunset from your private outdoor plunge pool. Accommodating up to 3 guests, it promises an intimate and unforgettable stay where every moment is bathed in the island's unique light.

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.

4.96 out of 5 average rating, 242 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.

4.89 out of 5 average rating, 240 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.

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.

4.95 out of 5 average rating, 118 reviews

An outdoor jacuzzi is surrounded by a spacious deck, offering a serene view of the caldera at twilight. Soft lighting reflects off the water's surface, creating a calming ambiance. The edge of the deck provides a clear line of sight to the distant lights across the water.

Home in Oia

Avax Villa by K&K (indoor & outdoor jacuzzi)

Avax Villa by K&K is a breathtaking house in Oia's caldera. Renovated in 2019, it features 3 bedrooms, 2 bathrooms, a living area, a kitchen and two jacuzzis, one indoor and one outdoor. Its minimal design is a perfect match to caldera's fierce beauty. The view, the energy and the feeling of serenity you get are hard to fit into words.

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.

Popular amenities for Oia waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

5 out of 5 average rating, 22 reviews

A sleek living area features a contemporary design, with a simple black table displaying a bottle of wine and a book. A television is positioned on a sculptural partition, complementing the minimalistic aesthetic. Natural light enhances the space, highlighting the white walls and decorative art.

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

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

Apartment in Pyrgos Kallistis

A serene outdoor space features a swimming pool surrounded by sun loungers and offers expansive views of the island and sea. The landscape includes distant hills and buildings, all under a clear sky, creating a peaceful atmosphere.

4.97 out of 5 average rating, 108 reviews

AROMA CAVAS APARTMENT WITH STONE AND PERFECT VIEW

4.98 out of 5 average rating, 236 reviews

A spacious terrace features a comfortable seating area with cushions, styled with a colorful blanket. The panoramic view overlooks the Blue Aegean Sea, framed by a clear blue sky. A small table is set with fresh fruit and a glass, inviting relaxation by the water.

Apartment in Kamari

Private Suite with Sea View

4.95 out of 5 average rating, 184 reviews

A private balcony is framed by an arched opening, providing an unobstructed view of the Aegean Sea and nearby islands. A wooden table accompanied by two folding chairs offers a relaxing space to enjoy the scenery and sunsets.

Apartment in Fira

Yposkafo Suites - Private Studio - Santorini

4.86 out of 5 average rating, 49 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

4.92 out of 5 average rating, 12 reviews

A spacious swimming pool is surrounded by lounge chairs under blue shaded canopies. Colorful inflatable floats are placed in the clear water, with the village buildings visible in the background. Sunlight reflects off the water's surface, creating a vibrant scene.

Home in Vlichada

Cosy Place for Families Pool&Beach

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

4.72 out of 5 average rating, 188 reviews

A private terrace features a hot tub with views of the sea and surrounding cliffs. Comfortable seating with soft pillows is placed near the edge, while a stylish basket and towels add convenience. The calming palette blends harmoniously with the serene landscape.

Home in Imerovigli

360° Caldera view Villa with hot tub & sea view

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, 8 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 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

Other waterfront vacation rentals

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, 72 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, 11 reviews

Uva Nera House Oia

4.98 out of 5 average rating, 46 reviews

An outdoor space features a private hot tub surrounded by a tiled area. Two sunbeds with a woven umbrella are positioned nearby. A table with two chairs holds plates and drinks, while a scenic view of the landscape and sea is visible in the distance.

Townhouse in Mesaria

Golden Moments Santorini Villa Rhapsody

Villa in Vourvoulos Beach

An outdoor terrace features a shaded seating area, including a hammock chair and a wooden dining table with chairs. The sea view in the background is framed by distant rugged hills and clear blue skies, creating a serene outdoor space ideal for relaxation.

4.98 out of 5 average rating, 64 reviews

Peaceful Seafront Retreat – Sonus Mare 1

4.99 out of 5 average rating, 74 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

5 out of 5 average rating, 18 reviews

A bright and airy room features a spacious double bed with a light-colored coverlet. Traditional blue-framed windows and doors allow natural light to fill the space. A small table with two chairs is placed nearby, complemented by two nightstands, each with a lamp.

Cycladic home in Fira

Caldera Cave House in Firostefani