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, 183 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

4.99 out of 5 average rating, 137 reviews

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

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.

4.86 out of 5 average rating, 139 reviews

An outdoor terrace is shown, featuring a dining table surrounded by light-colored chairs. A private jacuzzi is visible on one side, with panoramic views of the sunset over the sea and distant hills. The space is complemented by sheer drapes and a warm glow from the setting sun.

Villa in Firostefani

Sunset View Villa Santorini - Outdoor Jacuzzi

Exclusive Luxury Villa with breath-taking PANORAMIC views of the sea, Caldera & Sunset. Upstairs - One of the largest private jacuzzi terraces in Santorini with pergola & kitchen/bar, stunning views and Alfresco dining and lounging. Downstairs - 3 double Bedrooms, 2 bathrooms, lounge/dining room, Modern kitchen, outdoor dining table in the tranquil courtyard. Laundry with washer and drier. Daily clean, linen, towels & toiletries. Personal Manager & concierge services.

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, 271 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.

4.95 out of 5 average rating, 385 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.

4.98 out of 5 average rating, 132 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.

A view from the terrace features a custom-built hot tub with clear water, surrounded by whitewashed walls. In the background, a traditional blue-domed church tower stands prominently against a serene sea and sky, capturing the charm of the Oia landscape.

4.96 out of 5 average rating, 241 reviews

Bluedome Suite by Otium Villas & Suites

Bluedome suite is a renovated traditional cavehouse ideal for couples and small families. It has been built with the traditional Cycladic cavehouse architecture, carved in the Volcanic caldera rock. Its’ minimally designed spaces invite relaxation and comfort. The master bedroom (with en suite bathroom) is at the back of the cave connected to the living room and seating area, kitchen and second full bathroom, overlooking the patio and custom-built hot tub.

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

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.

A tranquil scene features a private hot tub overlooking the caldera, with clear blue waters stretching toward the horizon. A neatly arranged stack of towels and a cup accompany a magazine on the ledge, inviting relaxation against a backdrop of calm seas and distant islands.

4.85 out of 5 average rating, 261 reviews

Big Blue villa with Hot Tub and Sea View in Oia

Discover unparalleled luxury at our villa in Oia, Santorini. With breathtaking views of the caldera and impeccable design, our spacious accommodations offer a perfect blend of comfort and elegance. Enjoy a private hot tub, attentive hospitality from our dedicated staff, and the convenience of being located in the heart of Oia. Experience the epitome of relaxation and indulgence in this stunning retreat.

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.

4.95 out of 5 average rating, 116 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

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

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

4.99 out of 5 average rating, 134 reviews

A clear view of the deep blue sea is showcased, bordered by a scenic black beach. Lush palm trees and vibrant greenery frame the foreground, while traditional white structures dot the coastal landscape, indicating a serene atmosphere.

Apartment in Kamari

Kalipso Beach House

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 shaded outdoor seating area features wooden chairs and a small table, with a hot tub visible nearby. The background showcases the vast sea and a golden sunset, enhancing the tranquil environment. Light filtering through decorative curtains creates a serene atmosphere.

Apartment in Ormos Ammoudiou

4.63 out of 5 average rating, 82 reviews

Synergy Suite, 1 Queen Bed, Jetted Tub/Sea View

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

4.98 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, 183 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

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

4.38 out of 5 average rating, 8 reviews

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

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, 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-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

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

4.97 out of 5 average rating, 34 reviews

A dining area features a glass table surrounded by four plush chairs. A decorative piece hangs on the wall above, complementing the space. A wall-mounted television is visible, and a light fixture provides soft illumination in this simple and elegant setting.

Home in Vlichada

Santorini Villa Nev&4

Other waterfront holiday rentals

Earthen home in Akrotiri

5 out of 5 average rating, 13 reviews

Cave of Love – Seafront Sunset View Santorini

5 out of 5 average rating, 17 reviews

A private terrace is highlighted, featuring a heated jacuzzi surrounded by plush seating and decorative plants. A parasol offers shade from the sun, while expansive views of the Aegean Sea and caldera are visible in the background. Relaxation and tranquility are emphasized in this serene setting.

Cave in Oia

Aristos Life Luxury Cave Villa 2

4.79 out of 5 average rating, 43 reviews

A serene outdoor area features a small white table and two chairs positioned beneath a large tree. The space is surrounded by natural elements, including gravel and wooden structures, offering a quiet spot for relaxation. A sunhat rests casually on one of the chairs.

Hotel room in Fira

Standard Double Room with Sea View | Exi Sea Side

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

4.75 out of 5 average rating, 107 reviews

Villa Dakoronia•Stunning caldera view Private Pool

4.97 out of 5 average rating, 60 reviews

A hot tub is seen with bubbling water, situated outside against a backdrop of the sea. A large umbrella provides shade nearby, and a clear sky enhances the tranquil atmosphere of the space.

Cycladic home in Kamari

Studio & Jacuzzi Kamara Sea View

A private balcony features a glass table with a bowl of green apples and an open book. Two wooden chairs are positioned around the table, with vast panoramic views of the Santorini Caldera and expansive blue waters visible in the background.

Cycladic home in Fira

4.85 out of 5 average rating, 108 reviews

St. G Caldera | Spectacular Caldera View

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