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Oia Rentals

About Oia

178 villas

HELIOS or SISTERHOOD of traveling pants + hot tub

Oia house

1 bedroom / 1 bathroom / Sleeps 5

“Wonderful Getaway” We had an amazing stay at the Helios cave house. On arrival we were treated to a bottle of wine and some delicious nibbles on the terrace above the house, which Maria uses to welcome her guests. The view from the terrace is absolute

Responds fast! avg. 3 hours 34 minutes

$266

1 / 71

Skala Traditional Cave +outdoor Jacuzzi by Thireon

Oia cave house

3 bedrooms / 2 bathrooms / Sleeps 6

$925

1 / 29

BLUE & WHITE Cave House, Santorini, Oia + hot tub!

Oia villa

2 bedrooms / 2 bathrooms / Sleeps 4

“lovely with generous outdoor space” The Blue and White with it's stunning view is located just far enough below the main street,and a five minute walk to the sunset view, to give valued privacy.My daughter and I could enjoy breakfast,everything provid

Responds fast! avg. 3 hours 34 minutes

$232

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Villa Amalia sleeps 9 by Thireon

Oia cave house

4 bedrooms / 4 bathrooms / Sleeps 9

$696

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Oia Blue - sleek interiors in majestic setting

Oia villa

1 bedroom / 1 bathroom / Sleeps 2

“Best view in the world and utter relaxation in Oia!” This summer was our second stay at Oia Blue (the first was our honeymoon in 2010), and once again our stay was absoultely perfect in every way. The villa is in a perfect location, just off the bustl

Responds fast! avg. 3 hours 7 minutes

$214

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OIA SUNSET VILLAS - villa "TOPAZ" - Pool & Spa

Oia house

2 bedrooms / 2 bathrooms / Sleeps 6

$399

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GREEK PARADISE, outdoor Hot Tub, Caldera panorama!

Oia villa

2 bedrooms / 1 bathroom / Sleeps 4

“Amazing Greek Island experience” We rented both the Santorini Paradise and Helios houses for eleven people. They were absolutely wonderful. The views are spectacular. The houses were clean to start with and cleaned every day. Helios had just recently

Responds fast! avg. 3 hours 34 minutes

$232

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Ramni House with Pool and Beach by Thireon

Oia villa

3 bedrooms / 3 bathrooms / Sleeps 8

$1,101

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PINK Cave, 3 terraces outdoor jacuzzi Caldera View

Oia villa

3 bedrooms / 1 bathroom / Sleeps 4

“Incredible stay in an iconic home!” Maria was a wonderful host. She went out of her way to make us feel welcome and sat down with us and gave us a great overview of the island's activities. The house is iconic and is able to be seen on the postcards!

Responds fast! avg. 2 hours 31 minutes

$289

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3Arches Traditional House by Thireon

Oia villa

3 bedrooms / 3 bathrooms / Sleeps 6

$752

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CanavaView at Sunset with Jacuzzi by Thireon

Oia cave house

2 bedrooms / 1 bathroom / Sleeps 4

$752

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honeymoon house in oia village with caldera-sunset-sea view

Oia villa

1 bedroom / 1 bathroom / Sleeps 2

“Loved it” Simple dwellings in a clifftop, laid-back warm hosts who bring you home made cake for breakfast, listening to the waves at night, what else would you want? Very clean place, view of the sea and castle, but it definitely feels like part of a

$220

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Oia White - stunning Caldera views in Oia village

Oia villa

1 bedroom / 1 bathroom / Sleeps 2

Responds fast! avg. 3 hours 7 minutes

$215

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Two Bedroom Apartment in Amoudi Bay Sea View

Oia apartment

2 bedrooms / 2 bathrooms / Sleeps 5

$168

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Ninetta's house

Oia cottage

2 bedrooms / 1 bathroom / Sleeps 4

$208

1 / 17

Opuntia Traditional Cave at Blue Dome by Thireon

Oia cave house

2 bedrooms / 2 bathrooms / Sleeps 6

$752

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Casa Daphne

Oia house

3 bedrooms / 3 bathrooms / Sleeps 6

$730

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ARIS CAVES, Traditional Cave Houses

Oia hotel apartment

2 bedrooms / 1 bathroom / Sleeps 5

“Unforgettable” good service, very nice place, peacefull,warm. The home is nice, clean, well oriented., Unforgettable place and experience.

$405

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Oia Villa Clio

Oia villa

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 3 hours 33 minutes

$659

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The House of the Singing Birds

Oia house

1 bedroom / 1 bathroom / Sleeps 2

Responds fast! avg. 1 hour 19 minutes

$110

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Kristy Cave House

Oia house

2 bedrooms / 1 bathroom / Sleeps 5

Responds fast! avg. 2 hours 8 minutes

$405

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The House of the Seven Ships

Oia house

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 1 hour 19 minutes

$145

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Hector Cave house

Oia cave house

1 bedroom / 2 bathrooms / Sleeps 5

$289

1 / 19

White loft studio- shared terrace

Oia studio

Studio / 1 bathroom / Sleeps 2

$87

1 / 10

"The Annouso" villa in Oia

Oia house

2 bedrooms / 2 bathrooms / Sleeps 6

$217

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Hector Luxury Cave

Oia house

1 bedroom / 1 bathroom / Sleeps 4

$406

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The Sunny Winehouse

Oia house

1 bedroom / 1 bathroom / Sleeps 2

Responds fast! avg. 1 hour 19 minutes

$145

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Wineryhouse and two guest houses

Oia villa

4 bedrooms / 4 bathrooms / Sleeps 10

Responds fast! avg. 1 hour 19 minutes

$492

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OIA VILLAS 1: WHITE HOUSE CARVED IN THE ROCK- OUTDOOR JACUZZI

Oia villa

3 bedrooms / 2 bathrooms / Sleeps 5

$405

1 / 29

270 Oia's View Cavehouse V

Oia villa

1 bedroom / 2 bathrooms / Sleeps 4

$342

1 / 11

The Sunny Winehouse

Oia studio

Studio / 1 bathroom / Sleeps 2

Responds fast! avg. 1 hour 19 minutes

$128

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SiskosPlace Elias Cottage, Oia Santorini

Oia cottage

1 bedroom / 1 bathroom / Sleeps 4

$162

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Hector Caldera Nest

Oia room

1 bedroom / 1 bathroom / Sleeps 2

$174

1 / 8

SUNSET TERRACE, ourdoor jacuzzi, panoramic Sunset!

Oia house

2 bedrooms / 1 bathroom / Sleeps 6

“Beautiful Private Terrace” We had our host help us choose a space to enjoy the Oia sunset and light breeze. We had a big enough space to have a private catered dinner for 4 and a dance area where two musicians played the night away. We had use of the

Responds fast! avg. 2 hours 31 minutes

$232

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“This vacation will be hard to top.” Santorini was enchanting. The scenery was breathtaking. The Grand Canava was perfect. Plenty of room to spread out for a large group,. The breakfast was a great start to our day. Everything we needed was convenientl

$1,159

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BLUEDOME CAVEHOUSE OIA SANTORINI

Oia villa

2 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 3 hours 33 minutes

$856

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Luxury Villa at Oia with amazing view and pool

Oia villa

3 bedrooms / 3 bathrooms / Sleeps 9

“Discover this Jewel” After sailing around the Greek Islands on a charter we decided on a land holiday in the beautiful Oia. We are a group of 2 familes 8 persons from the moment our host met us at our transport everything we done to settle us into o

$671

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Als Mansion for a memorable stay in Oia Santorini!

Oia villa

3 bedrooms / 1 bathroom / Sleeps 7

$440

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About Oia

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It may be a popular destination for cruise ships, but the pretty village of Oia on Santorini has lost none of its charm.

Its location on the caldera affords visitors stunning sea views, with quaint houses nestled in the volcanic rock – a picture perfect location for your break.

About Oia

The island of Santorini is actually formed from the remains of a huge volcanic eruption, which destroyed a single island, creating the caldera and giant lagoon as we see them today.

Oia itself is as popular with artists and photographers as it is with cruise ship passengers and tourists, who come to enjoy this corner of the island of Santorini. Exploring on foot is a must, winding your way up and down the caldera through pretty cobbled streets and past traditional Greek houses and tavernas.

The Mediterranean climate means Santorini is pleasant to visit all year round, but for milder temperatures (and a less crowded atmosphere), April-June or September-October are the best months to explore Oia.

With over 800 vacation rentals in Oia to choose from on Flipkey, you'll find cottages, luxury villas with sea views, and traditional cave houses for an authentic Greek experience.

What to do

Pack your most comfortable shoes, as you’ll want to explore every corner of the caldera!

Ammoudi Port lies some 300 steps below Oia. Although it can be a sticky trek down and up again, it’s well worth it for the views of the harbor surrounded by red cliffs. While you’re here, why not take a boat tour to Thirasia, or stop for lunch at a tavern by the water’s edge?

If it’s art and culture you’re looking for, visit the Maritime Museum for a fascinating stroll through the island’s maritime history. Then stop off at Iatis Gallery. You can see the owner creating pottery and handcrafted jewelry – perfect for a souvenir of your trip.

No sunny day is complete without ice cream, and Lolita’s, near the bus station, has a range of classic and more unusual flavors to try – the rosewater is refreshing and so delicious!

Top Oia travel tips

Most of Oia’s attractions are reachable on foot and it’s possible to rent donkeys locally, as well as cars and scooters, if you wish to explore the rest of the island.

Oia is known for its sunsets, and one of the best places to enjoy the view is at one of the tavernas of Ammoudi Bay – here you can also enjoy grilled seafood caught fresh that day. Delicious!

If you decide to come to Santorini off season, try to avoid December to March. It can be cold, wet and windy here, and many businesses shut up shop for the winter.

There are few more charming clifftop villages than Oia, where you can dine on the freshest seafood, enjoy spectacular sunsets and relax in your FlipKey apartment or villa – why not search for your perfect vacation rental, today?

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