Waterfront vacation rentals in Oia

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Top-rated waterfront rentals in Oia

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Guest favorite

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

4.94 out of 5 average rating, 160 reviews

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!

Top guest favorite

A private balcony features a comfortable seating area with plush cushions and a wooden table. A view of the sea and nearby cliffs can be seen in the background, with the sun casting soft shadows across the space. Glassware and a pitcher rest on the table.

Cycladic home in Fira

4.99 out of 5 average rating, 119 reviews

Vacay Suites Queen Suite with Caldera View

Vacay Queen Suite offers an exquisite view of the caldera and the extraordinary sunset. The apartment is spacious (50m²) and fully equipment with a king size bed,living room with a double sofa bed,kichenette,dining area and private balcony. Ιdeal for couples, friends and families as well.Vacay Queen suite is seated 50m away from public parking spot and 10' away from Fira.Also there is a bus station in 150m.Plently of restaurants,cafeterias and mini markets are nearby the property.

Guest favorite

An outdoor area features a private Jacuzzi surrounded by low seating and oversized cushions, positioned for scenic views of the caldera. The white structure blends harmoniously with the natural landscape, complemented by a shade sail that provides protection from the elements.

Cycladic home in Imerovigli

4.93 out of 5 average rating, 315 reviews

Pure Life Cave House

When we acquired the Pura Vida Cave House it was a deserted Gem.. We immediately fell in love with the spot, on the top of a 300 meter cliff - nothing to block your sight but the end of the horizon. We put together a team to reconstruct it entirely, keeping the initial design of the house and blending it with modern touches and technology. The result is a Cycladic beauty, built into the rock, white as can be, to host a couple or a small family, in a fun and elegant environment!

Guest favorite

A serene outdoor seating area features two woven chairs facing the stunning sunset over the caldera. A small round table is placed between them, holding a bottle of wine and glasses. Grassy planters frame the space, enhancing the tranquil atmosphere.

Cycladic home in Fira

4.96 out of 5 average rating, 127 reviews

Revelis Villa

Excellent combination of spectacular view and unique position right in the heart of Fira town. Set in a peaceful neighborhood within easy reach to the main road and all the local attractions. The spacious outdoor area overlooking the magnificent volcano view and the unforgettable Santorini sunset is the ideal spot to relax any time of the day. The villa offers a mini pool, a hot tub, 3 bedrooms, 3 bathrooms, a living room, a kitchen and an outdoor dining table.

Guest favorite

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

4.95 out of 5 average rating, 375 reviews

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.

Guest favorite

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

4.98 out of 5 average rating, 125 reviews

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.

Guest favorite

A private terrace showcases a hot tub with sweeping views of the sea and surrounding landscape. A cozy lounge area, adorned with patterned cushions, invites relaxation under an archway, while a sunhat rests nearby, complementing the tranquil ambiance.

Cycladic home in Oia

4.93 out of 5 average rating, 155 reviews

3 Caves suite with Hot-Tub and Caldera View in Oia

Discover tranquility in the heart of Oia at 3 Caves Villa. This luxurious suite seamlessly blends traditional cave-home charm with modern comforts. With a private terrace boasting a bubbling hot tub and panoramic views of the sea, volcano, and caldera, relaxation is inevitable. Explore Oia's treasures within easy reach, then retreat to your cozy bedroom and sleek bathroom for a restful night. Welcome to your unforgettable Santorini escape.

Top guest favorite

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.

Cycladic home in Akrotiri

5 out of 5 average rating, 200 reviews

Akrorama Anemos - Private Pool & Caldera View

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.

Guest favorite

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.

Cycladic home in Oia

4.87 out of 5 average rating, 248 reviews

Bluedome Cavehouse by Otium Villas & Suites

This is a traditional cave house that has been newly renovated, situated on the cliffs of Oia. The house is amongst the most privileged, having a stunning view over the caldera, a breathtaking scenery that most have enjoyed only through postcards or advertising imagery. Only a few steps from the main road, right in the heart of Oia. Optional breakfast available with extra charge.

Guest favorite

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

4.89 out of 5 average rating, 235 reviews

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.

Guest favorite

An aerial view captures the coastline adjacent to the villa, displaying a rocky beach meeting the waves. Lush greenery and palm trees are seen along the shoreline. The villa's outdoor area features a patio space, bordered by a garden, providing a serene environment.

Cycladic home in Oia

4.9 out of 5 average rating, 162 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.

Guest favorite

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

4.95 out of 5 average rating, 110 reviews

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.