Cycladic house vacation 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, 345 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

4.96 out of 5 average rating, 112 reviews

An open-plan living area featuring textured stone walls and a high arched ceiling. A wooden dining table is surrounded by chairs, with a modern kitchen visible in the background. A cozy seating area offers comfortable sofas, while a small plunge pool is nestled in one corner.

Earthen home in Emporio

Canava Villas II - Heated Pool - Santorini

Villa#2 comes in 2 level floors and accommodates up to 6 people. On the ground floor there is a master bedroom, bathroom, fully equipped kitchen, lounge and WC. The upper floor provides 4 single floor mattresses or 2 double ones & its own bathroom. Outdoor private pool with Jacuzzi, patio, dinning area and sun lounges! Welcome drinks, basket of seasonal products, Nespresso coffee, Concierge services, A/C, Netflix, daily housekeeping, laundry services and many more amenities are waiting for you!

4.99 out of 5 average rating, 168 reviews

A heated plunge pool is featured within a uniquely shaped archway, with clear blue water reflecting the sun. A stunning view over the ocean and distant islands is visible through the opening. Decorative cushions and a small table with refreshments enhance the inviting atmosphere.

Villa in Imerovigli

Ventus Paradiso Villa, Outdoor Heated Plunge Pool

Our cave villa comes with sentimental value as it belonged to our grandmother. Dated back to 1920's brings a great heritage. The villa was totally renovated in 2015, transforming a traditional cave into a luxury residence following faithfully the unique cycladic architecture with exceptional modern esthetics. The villa consists of two bedrooms with ensuite bathrooms, a dining area and a small kitchenette. It features a heated plunge pool and an upper terrace with panoramic view over Caldera.

4.98 out of 5 average rating, 246 reviews

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.

Cycladic home in Fira

Sol

I-Sol is an isolated house in the center of the traditional village of Akrotiri! It has a two level outdoor! At the first level where is the entrance of the house you can relax on the dinning couch watching the caldera view! At the second level you will enjoy the sun and a 270 degrees view including the volcano relaxing at many choices such us the jacuzzi or the big sun beds or a couch or Acapulco style lounge chairs. Inside the house is a fully equipped kitchen , bathroom and two bedrooms!

4.99 out of 5 average rating, 104 reviews

A spacious terrace is highlighted with a white bench facing the calming Aegean Sea. The horizon features a gentle sunset, casting warm hues of orange and pink across the sky. Silhouetted mountains can be seen in the distance, enhancing the serene atmosphere.

Villa in Santorini

Anemi Villa - Sunset and Sea Views

A place to let the rest the world slips away. The ideal intimate escape! Anemi Villas is a beautiful example of the traditional Cave and Sea Captain Houses of Santorini, carved in the rocks of the magnificent caldera with panoramic views of the Aegean Sea, the Caldera Views and the famous Sunset of Santorini, It gives you the feeling of walking into a living postcard! Offering exceptional concierge service, Anemi Villas can turn your Holidays into an unforgettable life time experience!

A private plunge pool is visible in the foreground, reflecting clear blue water. The stunning caldera view features vibrant blue dome churches in the distance, with the Aegean Sea stretching out toward a clear sky. Whitewashed buildings create a serene backdrop.

4.97 out of 5 average rating, 306 reviews

Santorini blue, caldera views, private pool

Traditional Santorini cave house with famous blue dome churches, postcard perfect caldera views in the heart of Oia. next to main path.. Private plunge heated pool with panoramic views. Next to Island blue, Serenity &Eternity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities Other villas : Island blue, Eternity,Serenity,Captains blue, Secret garden, Sailing &Sky blue Flexible on pandemic related cancellations!

4.99 out of 5 average rating, 222 reviews

A private terrace features comfortable seating with plush cushions, small wooden table, and decorative bottles. The space provides a clear view of the deep blue ocean and surrounding caldera, complemented by the whitewashed buildings of Oia in the background and a bright blue sky.

Guest suite in Oia

Suite with 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. Right out of a post card between the two iconic blue domes of Oia. This suite has a private terrace with astonishing panoramic view to the caldera and the blue domes. Santorini International Airport is about 17 km from Oia Spirit, and the Ferry Port at approximately 23 km.

A tranquil outdoor jacuzzi is visible, with a view of iconic blue-domed structures nearby. The sun casts a warm glow, reflecting on the water. The serene ambiance is enhanced by the surrounding landscape, suggesting a peaceful retreat in a picturesque setting.

4.99 out of 5 average rating, 172 reviews

Santo Blue Horizon Villa | Jacuzzi | Caldera View

This unique villa is located in the heart of Oia in an excellent position and has stunning views. The famous Three Domes just in front of villa with panoramic view overlooking the santorinian caldera and the aegean sea, have magnetized visitors and photographers from all over the world, making it, the most popular spot in Santorini. The villa is in perfect harmony with the natural surroundings of the area and follows the principles of traditional Cycladic architecture.

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.

4.88 out of 5 average rating, 263 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.

4.9 out of 5 average rating, 146 reviews

The private terrace features a heated pool with crystal-clear water, overlooking a panoramic ocean view. Nearby, sun chairs are positioned to enjoy the scenery. Whitewashed walls and natural stone elements enhance the serene ambiance of the outdoor space.

Dome in Oia

Deluxe Villa with outdoor Jetted Tub & Sea View

Villa Paride is the luxury honeymoon suite, with private balcony and breath taking caldera-volcano view! Can accommodate till 2 persons. Totally renovated on 2019, with king size bed, new fully equipped kitchen, new bathroom with shower. Balcony with breath taking ocean-caldera-volcano view! Terrace with sun chairs, outdoor private heated pool / jet tube, umbrellas. FREE fast WI-FI

4.99 out of 5 average rating, 200 reviews

By the Mill, Caldera, Oia

100 sq meters of traditional cave house - 3 bedrooms and 3 bathrooms, spread over 3 levels of 100 square meters of private terraces and private plunge pool. At Oia's heart - incredible volcano, caldera & sunset views all year round. Easy access, and remarkable privacy, as well as daily housekeeping and plunge pool maintenance.... By the Mill is your dream Santorini home!

4.95 out of 5 average rating, 220 reviews

Cave in Oia

Satori Caves by Thireon

Welcome to Satori Caves - where the glittering sea meets the endless sky at the top of Oia’s breathtaking volcanic cliffs. The house has an amazing terrace with hot tub for your own private volcano viewing spot! There are a few steps to climb to reach this caldera home rewarding you with PRIVACY and away of the crowds. Managed by Thireon Houses

Popular amenities for Oia cycladic house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly cycladic house rentals

4.95 out of 5 average rating, 111 reviews

Villa in Karterádos

Villa Makrilis | Spacious Villa for Groups Jacuzzi

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, 178 reviews

Michelangelo Beach Villa with Sea View

4.94 out of 5 average rating, 281 reviews

A small white table is set on a balcony with a blue tablecloth and two glasses, overlooking a calm sea. A bottle of wine sits on the table, with views of distant islands visible under a clear sky.

Apartment in Oia

Blue Mirage

4.98 out of 5 average rating, 187 reviews

A modern villa is presented with a distinctive white dome roof, surrounded by greenery and blue sea views. A shaded patio features sun loungers beside a small swimming pool, providing a relaxing outdoor space. The bright blue doors complement the serene landscape.

Dome in Oia

MyBoZer Twins Odyssey Heated private pool

An outdoor seating area is featured under a wooden pergola, providing shade and comfort. Two orange chairs are placed near a small table, surrounded by vibrant flowers and greenery. The entrance to the home is visible through a large glass door, complemented by a nearby window.

4.9 out of 5 average rating, 104 reviews

Absolute peace south villa a place to chill

4.98 out of 5 average rating, 219 reviews

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.

Villa in Fira

Saints Apostles Villa with private pool

Cycladic home in Imerovigli

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.

4.94 out of 5 average rating, 325 reviews

Pura Vida Cave House

4.93 out of 5 average rating, 353 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 in Oia

Pano Meria Venetian Style Studio II

Cycladic house 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, 61 reviews

Lunar Sea Suite-1BR/Hot-Tub/Sea View

Cycladic home in Akrotiri

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.

4.87 out of 5 average rating, 23 reviews

Spilia Cave Nicole Santorini

4.94 out of 5 average rating, 16 reviews

Home in Pyrgos Kallistis

Thiro Exclusive Villa in Pyrgos

Cycladic home in Megalochori

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

4.93 out of 5 average rating, 14 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 in Mesaria

Euphemus Cave House

Cycladic home in Vourvoulos

4.94 out of 5 average rating, 66 reviews

Seafront Escape I Sonus Mare 2

4.87 out of 5 average rating, 39 reviews

The studio features a queen size bed, a cozy armchair, and a small wooden table. Closets with hanging space and a kitchenette equipped with a microwave and refrigerator are also visible. Soft lighting enhances the bright, airy atmosphere of the space.

Dome in Santorini

Elena Deluxe Studio (Sunny & cozy, near Caldera)

4.94 out of 5 average rating, 77 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.

Condo in Kamari

Nostos Apartments Kamari | Calypso

Cycladic house rentals with a washer and dryer

Home in Exo Gialos Karteradou

A relaxing moment by the private pool is captured, featuring clear blue water and a scenic view of the sea. A seated figure holds a glass of drink near an ice bucket, suggesting a tranquil atmosphere for leisure.

4.96 out of 5 average rating, 26 reviews

"Sand" sea view luxury villa with pool by beach !

4.67 out of 5 average rating, 117 reviews

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.

Apartment in Ia

Captain’s studio twin beds with sea view in Oia

4.85 out of 5 average rating, 66 reviews

The exterior of a traditional Venetian house from the 15th century is shown, featuring a blend of light-colored stucco walls. Windows with wooden frames are visible, and the architecture highlights the structure's historical significance. A clear blue sky serves as a backdrop.

Castle in Fira

Castelli Porta - Unique castle stay with sea view

4.91 out of 5 average rating, 80 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 in Oia

The Sunset Windmill

The property showcases a modern villa illuminated at dusk, featuring spacious lounge chairs by a tranquil pool. The serene mirrored water reflects the villa's elegant architecture, with soft lighting highlighting the entrance and surrounding greenery.

Cycladic home in Megalochori

4.88 out of 5 average rating, 43 reviews

Samsara - Santorini Luxury Retreat

4.88 out of 5 average rating, 17 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 in Kamari

Felicity Villas Santorini - Victoria

Apartment in Pyrgos Kallistis

A private hot tub is set in a bright, airy space with views of the sea and sky. Soft waves can be seen in the distance. Sunlight fills the room, highlighting the clean lines of the architecture and the serene atmosphere.

4.83 out of 5 average rating, 40 reviews

Genesis Suite with Caldera View and Hot Tub

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.