Cave vacation rentals in Oia

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Top-rated cave rentals in Oia

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Guest favorite

Cycladic home in Pyrgos Kallistis

4.99 out of 5 average rating, 215 reviews

Olyra Traditional Cave Houses

The traditional residences Olyra Traditional Houses, are in the heart of the medievial settlement of Pyrgos, very close to the imposing Kasteli (castle). A three minute walk in the stone laid pavements and side strees is enough to go from Olyra to the central parking of the village as well as the central square. Our houses are created in the same place where the bakery of the village was two centuries ago, with great respect and attachment to Santorinis¨ architecture. The decoration is character

Oct 23 – 30

G$27,561 GYD per night

Guest favorite

Cycladic home in Oia

4.98 out of 5 average rating, 209 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!

Jan 28 – Feb 4

G$89,544 GYD per night

Guest favorite

Apartment in Oía

4.99 out of 5 average rating, 100 reviews

Traditional Family Villa with Caldera View

Our Villa, situated just in the heart of Oia, offers a breathtaking view to the Caldera and the Aegean Blue waters. In a walking distance you can enjoy your shoppings as well as all famous restaurants and bars in the area. The villa can comfortably accomodate up to 5 guests, in two spacious bedrooms with double queen size beds each and a sofa bed in the living room area. Air-conditioned with kitchenette and free wi-fi. The balcony offers a dreamy view to the sea.

Mar 21 – 28

G$74,356 GYD per night

Guest favorite

Cycladic home in Oía

4.99 out of 5 average rating, 178 reviews

Anemi Karma- Private Villa with Sunset Views !

Anemi Karma House, our new part of our collection, is a Traditional Cycladic Cave House, located at the best spot in Santorini, to watch the breathtaking Sunset Views at the comfort and privacy of your balcony! Enjoy and revive, at our Anemi Karma House , upgrading your Holidays to an experience,as Dimitris, the Host, is very famous for his great Greek Hospitality offering high end tailor made services! We are looking forward to welcome you to our paradise!

Jun 23 – 30

G$156,538 GYD per night

Guest favorite

Cycladic home in Oia

4.91 out of 5 average rating, 120 reviews

SantoriniParadise: PARADISE cave, private hot tub!

Situated in the old part of Oia, it is the ideal accommodation for a romantic get away! Its sculpted rock architecture is unique and it has been beautifully decorated by its owner, Maria, a Greek sculptor & painter. The blue dome church of Saint Nicolas and the amazing sunset view is just a couple of minutes walk from PARADISE cave house. Feel free to experience our Cave winery in the depths of GREEK PARADISE! Its outdoor hot tub for 2 persons is private.

Dec 30 – Jan 6

G$51,290 GYD per night

Superhost

Cycladic home in Oia

4.8 out of 5 average rating, 224 reviews

Annouso House with Hot Tub and Caldera View in Oia

Embrace the allure of Annouso villa, where white stone, vibrant flowers, blue wood, and yellow terracotta converge to create a luxurious retreat. Our charming lodge boasts Santorini's most iconic views from its adorable balcony. Perfect for large friend groups or families seeking camaraderie and privacy. Experience the warmth of a cozy, home-like atmosphere wherever you roam. Annouso villa: your sanctuary amidst Santorini's splendor.

Oct 22 – 29

G$94,423 GYD per night

Guest favorite

Cave in Santorini

4.95 out of 5 average rating, 332 reviews

Hector Cave House

Hector Cave House, carved into the unique caldera cliff for more than 250 years, was originally used as a wine cellar. Then it became a family owned complex of three different properties that opened its doors to share its unique character to travelers from around the world. The three different listings one on top of the other: The Hector Cave House The Hector Luxury Cave The Hector Caldera Nest ΕΣΛ/Licence number: 1167K91000977901

Sep 25 – Oct 2

G$170,978 GYD per night

Guest favorite

Cycladic home in Oia, Thira

4.89 out of 5 average rating, 128 reviews

Astrea Suites: Ostria Cave Villa - Outdoor Jacuzzi

Ostria is the name of the south wind and the villa is named after the orientation of the house which is facing south towards the volcano and Santorini's caldera. This cave house situated in Oia, the crown jewel of Santorini, is a model of OIA's unique architecture, hanging from the cliff of caldera overlooking the volcano and the endless blue of the Aegean sea. Very near to the Castle, the most famous sunset!

Mar 18 – 25

G$89,319 GYD per night

Guest favorite

Cave in Oia

4.96 out of 5 average rating, 107 reviews

Angle Cave House 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.

Oct 23 – 30

G$97,042 GYD per night

Guest favorite

Apartment in Oía

4.98 out of 5 average rating, 206 reviews

Casa Itaca Fireplace Apartment

Luxury Italian-owned ground floor apartment in a classic Santorini cave house. The apartment is brand new and includes a fully-equipped kitchen,a private jacuzzi, a king size bed and a large shared yard .The apartment is located in Finikià,a small,peaceful village just 15 minutes walk away from Oia and the island's frenzy. Perfect if you want to enjoy a quiet and relaxing vacation.

Mar 17 – 24

G$32,380 GYD per night

Guest favorite

Cycladic home in Oia

4.85 out of 5 average rating, 224 reviews

Bluedome Cavehouse by Otium Villas & Suites

This is a traditional cave house that has been newly renovated, situated on the cliffs of Oia. The house is amongst the most privileged, having a stunning view over the caldera, a breathtaking scenery that most have enjoyed only through postcards or advertising imagery. Only a few steps from the main road, right in the heart of Oia. Optional breakfast available with extra charge.

Feb 7 – 14

G$147,593 GYD per night

Guest favorite

Cave in Oia

4.92 out of 5 average rating, 241 reviews

Pano Meria Cave House One in Oia

A unique cave house built into the face of the cliff overlooking the majestic caldera. Private plunge pool and terrace where you can spend the entire day admiring the views. The epitome of slow living in Oia. Fits up to three people and we can add a fold up bed.

Dec 2 – 9

G$144,697 GYD per night