
Cycladic house holiday rentals in Oia
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Top-rated cycladic home rentals in Oia
Guests agree: these cycladic home rentals are highly rated for location, cleanliness and more.

Eternity honeymoon suite,private pool caldera view
Honeymoon escape into panoramic views, famous blue domes churches,volcano & magical caldera! Eternity is the best romantic getaway in postcard perfect Oia Village.Private headed jacuzzi, verandas, historic 1 bedroom traditional home only steps from main street where all activities are. Fully equipped with all amenities, welcome basket,daily maid/pool service,villa manager to assist activities .Our other villas: Serenity,Island blue,Santorini blue,Captains blue,Secret garden,Sailing & Sky blue.

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 Boutique Residences, and the Ferry Port at approximately 23 km.

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.

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.

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!

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.

Deluxe Suite with External Jacuzzi,Caldera View
Deluxe Suite of 30 sqm-extrenal private jacuzzi. It has a double built-in bed, bathroom with shower and all the comforts ensure quality living conditions.Has view of the caldera,sunset and the volcano is a reference point for each guest.The 3 Luxury suites of La Casa De Caldera are on the same level.The yard of La Casa De Caldera is divided by dividers,into 3 pieces,each piece corresponding to each suite and every suite includes private sunbeds, private jacuzzi,private umbrella.

Divine View Collection
Our new Private cave house is renovated in 2017 and decorated by our interior designers with great taste and elegance, relaxing colours and romantic details. It has a double bedroom with an king size, built , double bed, and a loft with a double wooden bed , a large comfortable living room with one built sofa bed and a table with four chairs . There is an LCD cable TV, Wifi, a fully equipped kitchenette and a modern bathroom with a built shower place.

Bluedome Suite by Otium Villas Santorini
Luxury Cave Suite in Oia | Private Heated Jacuzzi | Sea & Caldera Views Wake up in a stylish cave suite carved from Santorini’s volcanic cliffs, just steps from Oia’s most iconic blue-domed churches and world-famous sunset spots. Designed for couples or small families who value modern comfort, traditional Cycladic charm, and panoramic views, Bluedome Suite at Otium Villas delivers a tranquil, unforgettable Santorini experience.

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.

Helianthus Honeymoon Cave Home
Our Prestige House is ideal for a memorable holiday experience in Oia. In its 50 square meters, the suite encompasses authentic Theran architecture with a modern twist . The heated outdoor Jacuzzi (it will be closed for the period of November 15th till March 15th) offers you the opportunity to dip in the water and enjoy the laid-back atmosphere and the stunning views to the deep blue sea , the volcano and the caldera!

Michelangelo Beach Villa with Sea View
Michelangelo Beach Villa is a perfect getaway destination for those seeking contact with nature and peace of mind. The villa is decorated in respect to the island's tradition, in pastel colors so our guests can take in as much of nature's and sea's beauty as they can. The fresh water hydromassage is not operating during December, January and February.
Popular amenities for cycladic home rentals in Oia
Family-friendly cycladic home rentals

Sublime Villa with sea view

Anatoli Beach House

LVNB 2 bedroom unique view villa in Imerovigli

Enalios House

Lithos Houses with private heated jacuzzi

Senior Suite Architect's Cave House

House of the Singing Birds.

Barocco Bello Villa
Cycladic home rentals with a patio

Lunar Sea Suite-1BR/Hot-Tub/Sea View

Spilia Cave Nicole Santorini

Apelia Santorini Holiday Villa with Pool and View

Petinos Traditional House

Euphemus Cave House

Beyond Crowds Seafront Escape | Sonus Mare 2

Elena Deluxe Studio (Sea view)

Nostos Apartments Kamari | Calypso
Cycladic home rentals with a washing machine and dryer

Leto Suite with Caldera View

"Sand" sea view luxury villa with pool by beach !

Captain’s studio twin beds with sea view in Oia

The Sunset Windmill

Exclusive Villa with Outdoor Heated Pool

Santorini Mayia Cave House with Private Cave Pool

Airth Suite (jacuzzi and sunset view)

Bluewhite villa with heated private pool
When is the best time to visit Oia?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $370 SGD | $371 SGD | $341 SGD | $294 SGD | $375 SGD | $446 SGD | $429 SGD | $438 SGD | $412 SGD | $307 SGD | $237 SGD | $370 SGD |
| Avg. temp | 12°C | 12°C | 14°C | 17°C | 22°C | 27°C | 30°C | 30°C | 26°C | 22°C | 17°C | 14°C |
Quick stats about cycladic house rentals in Oia

Total holiday rentals
Explore 140 holiday rentals in Oia

Nightly prices starting at
Oia holiday rentals start at $89 SGD per night before taxes and fees

Verified guest reviews
Over 13,600 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
140 of Oia holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oia rentals

4.9 Average rating
Oia stays are highly rated by guests – averaging 4.9 out of 5!
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