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Vacation Rentals & Villas in Oia

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Vacation Rentals & Villas in Oia

About Oia

879 villas

Villa Amalia sleeps 9 by Thireon

Oia cave house

4 bedrooms / 4 bathrooms / sleeps 9

Price per night from

$701

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Lydia's House - indoor heated splash pool, Caldera view

Oia villa

3 bedrooms / 2 bathrooms / sleeps 6

“A Corner of Heaven” Just checked out and felt like we were leaving home. House was some steps below the heart of the village and close to the Castle where people gather for sunset. Even so, it was private, quiet, clean, and oh so cool on days we came in from exploring the village. Maria's orientation with us was very helpful--she used a map to show us Santorini beaches and restaurants. Her name in those restaurants worked magic: complimentary wine and desserts, and excellent food, too. Different breakfasts were delivered to us each morning--heavenly to sit on the patio with nothing between us and the aegean. One bedroom was upstairs (could be warm) and one in basement, but three would sleep on main floor. Hands down, we three would go back in a minute!

Price per night from

$409

1 / 14

HELIOS or SISTERHOOD of traveling pants + hot tub

Oia house

1 bedroom / 1 bathroom / sleeps 5

“Magical Love” The host gave us access to the rooftop to celebrate my parents 40th anniversary with a surprise of the renewal of their vows. We decorated the space with green wreath and roses that the Host helped us with. The rate was perfect. If you need anything she can provide. The sunset was a spectacular one and we were extremely happy with the ceremony. We thank you Maria for making this happen -- THANK YOU SO MUCH!!

Responds fast! avg. 2 hours 36 minutes

Price per night from

$269

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Skala Traditional Cave +outdoor Jacuzzi by Thireon

Oia cave house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$936

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GREEK PARADISE, outdoor Hot Tub, Caldera panorama!

Oia villa

2 bedrooms / 1 bathroom / sleeps 4

“Living in a cloud” How can I express the wonderful feeling I had when I arrived to the home. We were received by Maria who has a heart of gold. She delivered and gave beyond what she had. We sat perched on the edge of a cliff overlooking the island and Fira dripping from the edge in white. As Maria went through all the best the island had to offer. The home was clean and beautifully decorated. It was a home that made you feel not only on vacation but also embodied the culture and style of Greece. You felt loved and at peace. You can be in that home to relax but in my case, I was surprising my parents with renewal of their vows so I was in close contact with Maria. I honestly did not expect the help she offered, and it was a lot. Making several calls and running around helping us with the details of a wedding. The catering, the flowers, the space. It was a full job for her. She seemed to do it all. Every morning our space was clean and we had fresh towels. If there was a request she was a phone call away. We had hotel amenities. Which is rare for a home rental to have. Over all - A spectacular home, amazing Service, Memorable time. We would go back again and can't wait to see Maria, this time to spend time with-- We highly recommend you go visit the black beach. If you have a concern ask Maria she is a wealth of knowledge. Do rent a car its easy to park and cheap to rent if you plan to check out the j

Responds fast! avg. 2 hours 36 minutes

Price per night from

$236

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Opuntia Traditional Cave at Blue Dome by Thireon

Oia cave house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$760

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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! The house is a very short walking distance to the central part of Oia and to the sunset viewing area. I can't say enough about how wonderful Maria and her beautiful home were-she even set up a private boat tour to the volcanic thermal springs for us with a wonderful guide named Sostis! What an incredible experience! Thank you, Maria!

Responds fast! avg. 2 hours 36 minutes

Price per night from

$295

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Hector Cave house

Oia cave house

1 bedroom / 2 bathrooms / sleeps 5

Price per night from

$292

1 / 19

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

Oia villa

2 bedrooms / 2 bathrooms / sleeps 4

“perfect.” location was perfect, view was breathtaking, decor was colorful and interesting. comfortable bed. quiet area of oia. this place is even more beautiful than the photos. i can't imagine a better experience

Responds fast! avg. 2 hours 36 minutes

Price per night from

$236

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Ninetta's house

Oia cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$211

1 / 17

"The Annouso" villa in Oia

Oia house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$199

1 / 24

CanavaView at Sunset with Jacuzzi by Thireon

Oia cave house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$760

1 / 19

Daphne House

Oia house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$736

1 / 30

Ramni House with Pool and Beach by Thireon

Oia villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,110

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Aqua & Terra superior private VILLA hot plunge pool and sea view

Oia house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 14 minutes

Price per night from

$526

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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 3 minutes

Price per night from

$217

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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 our very spacious accommodation the villa meanders over 3 floors with all the modern conveniences to make our stay so very comfortable. A cleaner arrives every morning you just indicate to your host what time would suit you. The vista is to die for lots of tourist make the trek to Oia jus for the sunset you can enjoy it from your own villa, there is a grocery / deli store a very short stroll along the ancient path with all your needs. The town boast up market not expensive stores and a large selection of amazing restaurants.. I also needed to get a item shipped, White house villa booked everything I just left my item in the villa on our departure and it was delivered for me. We will return

Price per night from

$683

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

Oia villa

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$330

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The Sunny Winehouse

Oia studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 34 minutes

Price per night from

$129

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SUNSET TERRACE, cave house , panoramic Sunset view !

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 bathroom and the chef had easy accessibility to the kitchen. It was perfectly decorated. A couple of lights allowed the night to magically glow. Thank you MARIA!!

Responds fast! avg. 2 hours 36 minutes

Price per night from

$236

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The Sunny Winehouse

Oia house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 34 minutes

Price per night from

$146

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Hector Caldera Nest

Oia room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$199

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The House of the Seven Ships

Oia house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 34 minutes

Price per night from

$146

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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 bustling main pedestrian street in Oia, however it is completely private and quiet due to its location below on the cliff's edge. The view is right out of postcard, with unobstructed views of the caldera. The villa itself is perfect for a couple and is tastefully decorated and professionally designed by a lovely Swedish architect who owns the house, along with her husband, Johan. The owners are also incredibly attentive and made themselves available to us at all times. In addition, the villa has a small kitchen and air conditioning (you don't need as it stays cool most of time). The town of Oia is fabulous - yes it is touristy during the day, but at nighttime it peaceful, and if you are foodie like we are, it is pure heaven, with countless restaurants to choose from. The only downfall is that it doesn't have a pool, but no private villas in Oia have pools, so it is a good idea to rent a car to go the beach during the daytime, or else there is a public pool nearby which is very nice. Free parking is nearby however you do need to walk about 5 minutes because Oia is a pedestrian town. In summary, we would highly recommend Oia Blue and will certainly be back ourselves again someday!

Responds fast! avg. 3 hours 3 minutes

Price per night from

$217

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Hector Luxury Cave

Oia house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$409

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Kristy Cave House

Oia house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 8 minutes

Price per night from

$409

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Blue Sky Cave House Oia Caldera

Oia cave house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$141

1 / 27

270 Oia's View House III, private swimming pool, Sunset view

Oia villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$456

1 / 26

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.

Price per night from

$409

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SiskosPlace Elias Cottage, Oia Santorini

Oia cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 9 minutes

Price per night from

$164

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The House of the Singing Birds

Oia house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 34 minutes

Price per night from

$111

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Sunset Studio

Oia house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 36 minutes

Price per night from

$292

1 / 32

Big Blue villa in Oia

Oia house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$222

1 / 21

By the Mill, Caldera, Oia - private, spacious, sunset and volcano views

Oia villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$561

1 / 35

The White cavehouse in Oia

Oia house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$189

1 / 15

Oia Villa Clio

Oia villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 33 minutes

Price per night from

$666

1 / 27

BLUEDOME CAVEHOUSE OIA SANTORINI

Oia villa

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 33 minutes

Price per night from

$865

1 / 24

Wineryhouse where dreams live......

Oia house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 34 minutes

Price per night from

$205

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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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