Cycladic house vacation rentals in Santorini caldera

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Top-rated cycladic house rentals in Santorini caldera

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Guest favorite

A scenic view is framed by an open window, showcasing the deep blue sea and distant boats. On the windowsill, a bottle of wine rests beside two glasses and a travel guide, hinting at a relaxing atmosphere and exploration.

Hotel room in Oia

4.88 out of 5 average rating, 251 reviews

mu perfect house with caldera sunset view

Really a authentic cavehouse on caldera with unique view, around has only white cavehouses. the house isin oia village, on caldera. is ideal for honeymoon and relax holidays.the house is private, has a private patio with table and chairs. has seaview and from inside! around has the best restaurants and many shops , travel ofices and gallerys, also you can to rent car or moto. the house has aircontition and free wifi. also we provide towels and sheets and bathroom amenities. MHTE1167K050B0902201

Guest favorite

An outdoor seating area offers stunning views of the caldera. Whitewashed walls frame a small table surrounded by chairs, complemented by built-in seating along the edges. The bright blue sea and sky create a serene backdrop, inviting relaxation and enjoyment.

Cycladic home in Fira

4.97 out of 5 average rating, 115 reviews

Yposkafo Suites - Villa - Santorini Firostefani

Studio "Yposkafo" beautifully blends tradition, elegance, and comfort, offering an unforgettable stay in one of the island’s most stunning locations. Perched on the Caldera, it is just steps from the iconic "Three Bells of Fira" and only a 7-8 minute walk from the town center. The studio boasts a luxurious indoor jacuzzi, a king-size bed with a brand-new orthopedic mattress, and a spacious private terrace with sweeping views of the Aegean Sea, the famous Santorini sunset, and the volcano.

Top guest favorite

An airy interior space features smooth white walls, gently curving arches, and a soft light illuminating the area. A textured pouf is placed on a neutral rug, while decorative elements, including a vase and small lanterns, add a touch of character.

Cycladic home in Santorini

4.99 out of 5 average rating, 176 reviews

Anemi Lovers House - Sunset and Sea View

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!

Superhost

Dome in Mesaria

4.96 out of 5 average rating, 141 reviews

Marla Villas - Cave House

Marla Villas is located in the traditional settlement of Mesaria. That means it is truly beautiful and peaceful and quiet but NO cars allowed. If you rent a car, you can park at the main road which is 4-5 min walking distance. If you rent a scooter, you might find a parking next to the house, but if not, 3-4 min walking I think is ok. It's an old cave house, fully renovated in 2017. In the neighborhood there are many traditional buildings and houses and the security is on high level.

Superhost

An open living space features a kitchen area with modern appliances and wooden cabinetry. A cozy dining table is paired with three stools. The room is highlighted by a comfortable seating area, with two sofa beds situated in the background, creating a welcoming and functional environment.

Cycladic home in Imerovigli

4.93 out of 5 average rating, 307 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!

Guest favorite

A light-filled doorway leads to a spacious terrace overlooking a bright blue sea. White furniture is visible on the terrace, with an umbrella providing shade. The interior features a polished white floor and soft blue accents framing the entry.

Cycladic home in Oia

4.98 out of 5 average rating, 247 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!

Top guest favorite

Cycladic home in Imerovigli

4.96 out of 5 average rating, 226 reviews

Sea Horizon

The time has come for me to make my own paradise available to you. Sea Horizon is the new ideal getaway for romantic holidays. Unique seaview, breathtaking sunrises! Reflecting the traditional Cycladic architecture, the villa provides the utmost in privacy and comfort. Feel like home and relax in the private swimming pool! Welcome basket with fruits and wine! We love making our guests happy! Celebrate your special occasion with us and enjoy a complimentary cake!

Top guest favorite

A bright living area is presented with a modern gray sofa adorned with decorative cushions. Natural light pours in through two windows, highlighting a round wooden table set for breakfast. A neutral woven rug is placed beneath the table, inviting a relaxed atmosphere.

Cycladic home in Fira

4.92 out of 5 average rating, 398 reviews

Divine View Sun Home

Unwind and relax with a glass of wineadmiring the breathtaking views of the famous Santorinian sunset from this house's private veranda . Awake refreshed and ready for a day to explore the island via this clean, sunny house with impressive views to the caldera , volcano of Santorini Aegean Sea & the island of Thirassia . Head out and wander through the famous paths of Fira and explore the nearby little shops & cafe .

Top guest favorite

A serene sunset view over the ocean showcases vibrant hues of orange and purple in the sky. The private plunge pool glows softly, surrounded by white-washed terraces. Traditional architecture blends seamlessly with the natural landscape, offering a peaceful and secluded atmosphere.

Cycladic home in Oia

4.99 out of 5 average rating, 169 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!

Guest favorite

A spacious terrace overlooks the ocean, featuring two white lounge chairs and a central table. Decorative stones are placed along the edge, and a selection of fresh fruit is displayed on the table. Clear blue skies and calm waters create a serene backdrop.

Cycladic home in Imerovigli

4.91 out of 5 average rating, 129 reviews

Anatoli Beach House

Cliff side house, above the beach, panoramic view and breathtaking sunrises! Anatoli beach house combines Cycladic style, comfort and tranquility! The kitchen is fully equipped. We welcome you with a bottle of wine and fruits. Feel like home! We love making our guests happy! Celebrate your special occasion with us and enjoy a complimentary cake!

Superhost

A modern balcony is showcased, featuring a light blue table and two wooden chairs. A bowl of fruit sits at the center, with the expansive view of the Santorini Caldera and surrounding cliffs visible in the background, under a clear blue sky.

Cycladic home in Fira

4.85 out of 5 average rating, 104 reviews

Caldera St. G | Spectacular Caldera View

This newly renovated accommodation offers breathtaking panoramic views of the Santorini Caldera and its volcanoes. Inside, a cozy minimalist design blends seamlessly with modern Cycladic charm. Step onto the balcony and take in the stunning Caldera landscape, where each sunset transforms the sky into a masterpiece of colors.

Guest favorite

A serene terrace features two folding chairs positioned beside a small circular table. The scene is complemented by a soft sunset glow and distant views of the sea, framed by white-washed buildings and lush greenery, creating a peaceful retreat.

Cycladic home in Finikia

4.9 out of 5 average rating, 232 reviews

Villa Florina

VILLA FLORINA Originally built in 1890, situated in the heart of Finikia, one of Santorini’s most beautiful traditional villages. 3 small houses, two courtyards, two terraces. Ideal for families/friends. Calm, car free, restaurants & amazing sunsets. You need to walk ca. 100m into Finikia to access the house.