Cycladic house vacation rentals in Southern Aegean

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Top-rated cycladic house rentals in Southern Aegean

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Guest favorite

Cycladic home in Oía

4.95 out of 5 average rating, 194 reviews

Helianthus Honeymoon 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 1/11-15/3) 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

Jan 2 – 9

G$145,826 GYD per night

Guest favorite

Cycladic home in Oia

4.97 out of 5 average rating, 257 reviews

Historic cave house, the old bakery by Cycladica

The old bakery of the village awaits just two minutes from Oia's central square, with a private entrance right on top of the stairs that lead to Armeni bay. Carved in the mountain with respect to the unique local architecture and in harmony with the sun-filled, wild volcanic beauty, the newly restored cave house recounts stories of tradition, heritage and style. The red pumice stones, antique marble floors and handcrafted wooden furniture, create the feeling of an authentic warm hospitality.

Jan 24 – 31

G$109,817 GYD per night

Guest favorite

Villa in Imerovigli, Santorini, Thira, Cyclades

4.98 out of 5 average rating, 105 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.

Jan 18 – 25

G$100,883 GYD per night

Guest favorite

Cycladic home in Thira

4.97 out of 5 average rating, 160 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!

Apr 12 – 19

G$32,235 GYD per night

Guest favorite

Guest suite in Oía

4.98 out of 5 average rating, 149 reviews

Suite with Outdoor Plunge Pool & 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. This suite additionally features a private outdoor plunge pool. The view from its terrace is stunning, featuring the caldera and the two iconic blue domes of Oia. Santorini International Airport is about 17 km from Oia Spirit Boutique Residences, and the Ferry Port at approximately 23 km.

Nov 10 – 17

G$91,494 GYD per night

Guest favorite

Cycladic home in Oía

4.95 out of 5 average rating, 199 reviews

Bluedome Suite by Otium Villas & Suites

This is a newly renovated cavehouse that dates back to the 1890's. Situated in one of the most famous neighbourhood's in Oia "Monastiraki" next to the famous St Spyridon Bluedomes. It has been renovated keeping traditional cycladic cavehouse architecture at the forefront of the design while utilising modern building materials. This suite is ideal for couples and families. Its' minimal designed spaces inspire relaxation and comfort for the modern traveller.

Mar 23 – 30

G$73,981 GYD per night

Guest favorite

Cycladic home in Milos

5.0 out of 5 average rating, 188 reviews

Villa Tasoula Sunrise apartment

Villa Tasoula it's located 1km from Adamas downtown ,built with Cycladic architecture it is separated in two floors. Upstairs live my family,at the first floor we made 4 places for hosting. Two apartments and two studio. The Sunrise apartment 45 sq.m. fully equipped available for 3 person.there is not sea view but it is 150 meters from the beach of papikinou, ιdeal for relaxing and pleasant holidays !

Oct 13 – 20

G$26,453 GYD per night

Guest favorite

Apartment in Oia

4.97 out of 5 average rating, 115 reviews

Angel Studio with Jacuzzi and Sunset View

An amazing suite, that respects the traditional architecture of Santorini, with a breathtaking view of Caldera and the famous sunset of Oia. Literally hanging over the cliffs of Oia overviewing Ammoudi Bay, which lies within walking distance. The accommodation is a spectacular location, however there are few steps to get there, nothing too demanding for someone who is an abled walker.

Apr 6 – 13

G$97,285 GYD per night

Guest favorite

Cycladic home in Oia

4.99 out of 5 average rating, 147 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!

Apr 29 – May 6

G$219,067 GYD per night

Guest favorite

Cycladic home in Megalochori

4.96 out of 5 average rating, 215 reviews

Villa Ruby

Villa Ruby is located in the traditional village of Megalochori in Santorini. A new villa built in the traditional architecture of the island. This accomodation is situated 3 kilometers from the Port, 7 kilometers from the Airport, 6 kilometers from the cosmopolitan center of the island and 4 kilometers from the islands' amazing beaches.

Mar 28 – Apr 4

G$19,297 GYD per night

Superhost

Cave in Oia

4.91 out of 5 average rating, 273 reviews

Skala Cave-by Thireon

Live the ultimate Santorini dream in the heart of world-famous Oia, imbued with the spirit of chic luxury. Perched high atop the caldera cliffs, the infinite views of the glittering sea and sky will take your breath away. A fully serviced property managed by Thireon Houses

Oct 25 – Nov 1

G$135,073 GYD per night

Superhost

Villa in Ia

4.86 out of 5 average rating, 198 reviews

Top Caldera view villa with Hot Tub in Oia

This spacious little villa is located at the highest point of the village with stunning and unlimited views to the famous caldera and the volcano. The king size bed and the hot tub at the balcony will give unique moments of relaxation and enjoyment

Oct 3 – 10

G$161,176 GYD per night