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Cycladic house vacation rentals in Regional Unit of Islands

Find and book unique Cycladic house rentals on Airbnb

Quick stats about cycladic house rentals in Regional Unit of Islands

  • Total vacation rentals

    Explore 90 vacation rentals in Regional Unit of Islands

  • Nightly prices starting at

    Regional Unit of Islands vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    90 of Regional Unit of Islands vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Regional Unit of Islands rentals

  • 4.8 Average rating

    Regional Unit of Islands stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Regional Unit of Islands’s top spots, include Acropolis, Plaka, and Acropolis Museum

Top-rated Cycladic house rentals in Regional Unit of Islands

Guests agree: these Cycladic house rentals are highly rated for location, cleanliness, and more.

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Guest favourite
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.
Earth homes in Emporio
4.97 out of 5 average rating, 115 reviews

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!

Top guest favourite
A private heated pool is seen on a terrace, offering unobstructed views of the deep blue sea and distant islands. The scene includes iconic white buildings with blue domes, set against a clear sky, showcasing typical Santorini architecture.
Cycladic homes in Oia
4.95 out of 5 average rating, 409 reviews

Island blue, postcard perfect view & private pool

Traditional cave house located in the most famous location in Santorini Island with breathtaking postcard perfect views of the blue domed churches! 2 bedrooms, double beds 2 cave bathrooms. Outdoor heated pool with view! Next door to Santorini blue, Eternity & new home Serenity. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist with all activities. Our other villas Santorini blue,Eternity,Serenity,Captains blue, Secret garden,Sailing & Sky blue

Top guest favourite
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
4.99 out of 5 average rating, 173 reviews

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.

Top guest favourite
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 homes in Fira
4.98 out of 5 average rating, 251 reviews

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!

Guest favourite
A Greek Fisherman's House is depicted, featuring a white exterior with a red-tiled roof and three sets of blue windows, facing the beach. The surrounding area includes lush greenery, and additional buildings can be seen in the background against a clear blue sky.
Tiny homes in Gytheio
4.91 out of 5 average rating, 139 reviews

Authentic Greek Fisherman's House 1 - Summer Love

This house has a full fridge and a private balcony, no guests pass through your balcony. Please also check "Love House" and "Love Nest" Houses for availability. House is on the beach. This place is good for couples, solo adventurers, LGBTQ+ firiendly, business travelers and pet firendly. You will wake, eat, live, sleep, dream on the beach! Place is unique, it is like living on a Yacht with the luxury of a house. Now it is divided in three separate houses, sharing the same beach.

Top guest favourite
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 homes in Imerovigli
4.94 out of 5 average rating, 329 reviews

Pura Vida 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!

Top guest favourite
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
4.99 out of 5 average rating, 229 reviews

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.

Top guest favourite
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 homes in Oia
4.88 out of 5 average rating, 268 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.

Top guest favourite
The private terrace features a dining table and reclining chairs, set against a backdrop of a golden sunset over the caldera. The expansive sea view includes distant hills and whitewashed buildings, creating a serene atmosphere for relaxation.
Cave in South Aegean
4.93 out of 5 average rating, 389 reviews

Soundscape - cave suite panoramic sea views

Within walking distance (only 7min walk) from Fira, the capital of the island, for shopping, museums and nightlife, Firostefani village is very peaceful and away from the crowds . There are plenty of things to explore on the island like museums, archaelogical sites, activities, beaches or just relax and enjoying the picturesque sea views plus that I am here to make sure you have everything you need and make you feel like home :)

Top guest favourite
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 homes in Akrotiri
5 out of 5 average rating, 234 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.

Guest favourite
An outdoor area features a stonewall backdrop with a staircase leading to a door. A circular hanging chair and a dining set with gray chairs are present. Cushions are arranged on a raised platform, while a tray with fruits is placed on the table.
Cycladic homes in Megalochori
4.93 out of 5 average rating, 178 reviews

Antonio Caves

Antonio Caves are a typical example of Santorinian architecture. Constructed in 1901, it was initially used as cave house wine preparation cellar and a bakery built right into the volcanic rock. In 2020 it was renovated completely and converted into 3 autonomous suites sharing a common courtyard Situated in the traditional village of Megalochori in two minutes walking distance from the picturesque square of the village

Top guest favourite
An illuminated cave pool is surrounded by smooth curves of stone walls, highlighting the modern design. The warm water reflects soft blue tones, creating a serene ambiance in the space. An indirect light source enhances the unique features of the pool area.
Cycladic homes in Pyrgos Kallistis
4.96 out of 5 average rating, 302 reviews

Santorini Mayia Cave House with Private Cave Pool

Discover the real Santorini, beyond the crowded touristic routes. Mayia Cave House is a renovated 19th century traditional cycladic cave house in the quiet medieval village of Pyrgos. Offers all modern amenities, a spectacular private large warmed cave pool, a private hot tub in the terrace and incredible views over Santorini, including the famous sunset.

Popular amenities for Regional Unit of Islands Cycladic house rentals

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