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Cycladic house vacation rentals in Santorini Caldera

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Top-rated cycladic house rentals in Santorini Caldera

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

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Guest favorite
A bright living area features white-washed walls and a spacious seating area with decorative pillows. Two wooden stools are positioned near a dark wooden coffee table. Large windows open to stunning views of the caldera, allowing natural light to fill the space.
Guest suite in Oia
4.95 out of 5 average rating, 218 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 balcony with astonishing panoramic view to the caldera and the blue domes. Santorini International Airport is about 17 km from Oia Spirit Boutique Residences, and the Ferry Port at approximately 23 km.

Top guest favorite
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, 157 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 favorite
Cycladic home in Oia
4.94 out of 5 average rating, 265 reviews

Apanema Suite by Otium Villas Santorini

Luxury Cave Suite in Oia | Private Heated Jacuzzi | Front-Row Caldera Views Experience Santorini from the front row at Apanema Suite, a luxury cave suite in Oia offering unobstructed caldera and sunset views. Designed for guests who value privacy, refined comfort, and breathtaking scenery, this elegant suite delivers an intimate yet elevated island experience. With its prime cliffside position and authentic Cycladic design, is ideal for couples seeking a romantic escape with iconic views.

Top guest favorite
A private Jacuzzi tub is positioned on a balcony, with a stunning view of the Aegean Sea and a sunset reflecting on the water. Soft clouds are visible in the sky, and a rolled towel is neatly placed beside the tub.
Villa in Vourvoulos
4.89 out of 5 average rating, 142 reviews

Levantis Suite - Private Hot Tub & Sea View

Levantis Suite (57 sq.m.) at La Estrella Luxury Suites embodies refined Cycladic elegance, perched in serene Vourvoulos just 600 m from Imerovigli. Offering uninterrupted Aegean Sea views, it features a heated private jacuzzi on the balcony, exquisite décor, premium amenities, daily housekeeping, and private parking. Ideally located near a mini market (400 m) and charming local tavernas (350 m), the suite is only 1.3 km from the Caldera, set in a peaceful and quiet area of Santorini.

Guest favorite
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.
Cycladic home in Oia
4.97 out of 5 average rating, 293 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
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, 128 reviews

Yposkafo Suites - Villa - Santorini Firostefani

Villa "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. Boasts a luxurious mini pool, indoor jacuzzi, a king-size bed, a queen size bed, 4 sofa/beds, and a spacious private terrace with sweeping views of the Aegean Sea, the famous Santorini sunset, and the volcano.

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, 216 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.

Superhost
A spacious living area is highlighted by a light grey sectional sofa, complemented by decorative pillows. Two small tables sit in front, with a potted plant adding a touch of greenery. Three woven wall hangings provide texture against the neutral backdrop.
Home in Karterádos
4.91 out of 5 average rating, 136 reviews

ASPRO traditional luxury house

Located at the traditional Karterados area of Santorini, ASPRO traditional luxury house, fully renovated in 2018, is a place where Cycladic architecture meets the luxurious accommodation. It is ideal for couples, families, friends and travelers wishing to live the unique experience of staying in a traditional Santorini house with all modern facilities. Centre of Fira town lies within 1,5 km (15 minute walking distance).

Superhost
An infinity pool glistens in the sunlight, with a wooden pergola providing shade over a lounge area. The surrounding landscape is characterized by hills and a clear blue sky, enhancing the serene atmosphere of the villa.
Cycladic home in Santorini
4.82 out of 5 average rating, 108 reviews

Bluewhite villa with heated private pool

Situated in the traditional village of Pyrgos Kallistis, the heart of Santorini island, my place offers a stunning panoramic view of sunrise and the Aegean Sea. The 130m² Villa features luxury, privacy, easy access and comfort in Cycladic style combined with modern design and decoration. Our new infinity pool is a must! Please note that the pool is functional only for the spring and summer season March 15- October 31st

Top guest favorite
A spacious balcony features an externally heated jacuzzi, illuminated by subtle lighting. The moon casts a gentle glow over the serene sea and distant coastline, while a muted landscape is visible in the background, creating a tranquil nighttime atmosphere.
Cycladic home in Exo Gonia
4.98 out of 5 average rating, 124 reviews

Terra e Lavoro Suite with Hot Tub & Sea View

The exceptional space of Terra e Lavoro in Santorini was ideally designed to offer a personalized experience of enjoyment to those seeking a luxurious retreat on their vacation. The Terra e Lavoro luxurious apartment in Exo Gonia is a modern Villa in Santorini with traditional architecture, ready to welcome its guests and lead them to unique moments of relaxation.

Top guest favorite
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.
Apartment in Fira
4.98 out of 5 average rating, 206 reviews

Saints Apostles Villa with private pool

Saints Apostles is located in a quite area 1,5 klm from Fira town (20 minutes by walking or 2 minutes by car). Is fully luxury furnished , unlimited sea view to the east side of the island (on the beach side) and to the sunrise. The house is divided in 2 villa apartments with each apartment been private with its one swimming pool and all the amenities we describe.

Top guest favorite
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 home in Pyrgos Kallistis
4.96 out of 5 average rating, 285 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 Santorini Caldera cycladic house rentals