Vacation Rentals & Villas in Oia

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895 villas

SantoriniParadise: PINK Cave, 3 terraces outdoor jacuzzi Caldera View

Oia villa

3 bedrooms / 1 bathroom / sleeps 4

“Great location! Very nice host!” We really enjoyed staying at Maria's pink cave house! She was very helpful & the house was in the best location, great views of Oia and the sunrise.

Price per night from

$332

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

Oia villa

2 bedrooms / 2 bathrooms / sleeps 4

“Great location” Great location with beautiful view, spacious cave house. Sergio was very helpful in showing us around and taking us to the room. Enjoyed our stay very much!

Price per night from

$267

SantoriniParadise: PARADISE, outdoor Hot Tub, Caldera panorama!

Oia villa

2 bedrooms / 1 bathroom / sleeps 4

“Beautiful property wonderful views beautiful island” This is a well appointed property well kept clean and welcoming stunning views and friendly locals wonderful shops and plenty to do and see ....lots of steps so not for people with mobility problems most enjoyable holiday .

Price per night from

$267

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

$447

“It Doesn't Get Any Better Than This!” I took my teenage son on a 2 week trip around Greece and I am so thankful that I saved Helios House in Oia for our last stop because it was truly the most perfect and magical spot. Nothing could have topped our time there. First, the Cave House is breathtaking. It is fresh, clean, cozy, cool, and well-stocked for breakfast and drinks.. It is newly remodeled with a modern deep tub that will make you relax and never want to get out! Next is the owner, Maria. She would get 10 stars from me! She explained the house, and the flow of the day in Santorini, and was available for anything we needed. Her adorable elderly neighbors will make you feel like you are living the Greek life, so authentic and real. Then, the sunset. Maria has one of only a handful of private patios that have a 100% direct view of the sunset. It is amazing to watch people flock to view the glorious red sunset every night, all standing along the walkways, while we were there sitting comfortable on our deck drinking wine and snacks prepared by Maria and her sweet neighbors. I loved it there. I felt like I was really in Greece and had the feeling of family, yet also had all the privacy we wanted. Finally, the long steps down to the sea is a must! Perfect location to take your time, walk down the steps, take a dip in the sea, snorkel or jump off the famous rock, eat lunch and then make your way back to paradise inside your Cave House. We will be back!

Price per night from

$268

Hector Cave house

Oia cave house

1 bedroom / 2 bathrooms / sleeps 5

Price per night from

$498

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

$787

Big Blue villa in Oia

Oia house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 36 minutes

Price per night from

$318

BLUEDOME CAVEHOUSE OIA SANTORINI

Oia villa

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 48 minutes

Price per night from

$919

The House of the Seven Ships

Oia house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 46 minutes

Price per night from

$166

Ilivatos Oia .. The house of your private escape

Oia house

4 bedrooms / 4 bathrooms / sleeps 10

“We fell in love with Ilivatos” The beauty in and around Ilivatos was lifting us up and we could not express in words sometimes how we feel. Amazing view and so cosy and comfortable, the house had everything we enjoyed!! And there is a big treasure ! Raymont. To see him how much love he brings to the house to make it everyday nice and clean... serving us breakfast and it was to him nothing too much. Taking care of the sun deck and and...so wonderful. We also appreciate the pick up service and carrying all our luggage to the house and all information we need!!! thank you Rajmont!! Booking the house was very well organized and I had always a very fast reply and I had so much support with Mrs. Irene thank you,it was a pleasure and we will come back to this little paradise.

Price per night from

$1,021

"The Annouso" villa in Oia

Oia house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 36 minutes

Price per night from

$255

“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!!

Price per night from

$230

Ammos Oia Mansion

Oia villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$698

Oia White - stunning Caldera views in Oia village

Oia villa

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 4 minutes

Price per night from

$243

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

Oia villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$868

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

Oia villa

3 bedrooms / 2 bathrooms / sleeps 5

“Great place to stay In Santorini” Incredible view and incredible place to stay in Santorini! The house is amazing. Oia is the place to be on the island.

Price per night from

$447

SiskosPlace Elias Cottage, Oia Santorini

Oia cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 20 minutes

Price per night from

$178

Kristy Cave House

Oia house

2 bedrooms / 1 bathroom / sleeps 5

“Wonderful place and amazing hostess” We had a wonderful trip to Greece and Santorini was a great experience partly due to our stay at the Kristy Cave House and Christina. She was extremely helpful and efficient. She contacted us before our arrival and set up a driver to pick us up at the port. Our driver, Yannis, by the way was also great and pointed out all the interesting places for us to visit in Oia. Christina met us at the house and showed us the house as well us pointing out all the areas of interest. She recommended a cruise line and I would recommend to everyone as it was one of the highlights of our trip.

Responds fast! avg. 2 hours 27 minutes

Price per night from

$457

The House of the Singing Birds

Oia house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 40 minutes

Price per night from

$122

Oia Blue - sleek interiors in majestic setting

Oia villa

1 bedroom / 1 bathroom / sleeps 2

“Spectacular accommodation hanging on the cliffs of Oia” We stayed in Oia Blue from May 6-13. The cave house was exactly as described. Very well appointed, clean and comfortable. It had all the amenities one would need. The house is just a couple flights down from the main thoroughfare and in the central part of the town. This means the house is quiet and peaceful while still being in the center of the things. The owners Johan and his wife Vivi could not have been more attentive. They gladly arranged for transfers from the ferry and back to the airport plus any other request we had during the week, which included a porter to assist with our luggage at departure. In all a fantastic week. Thank you Johan and Vivi.

Responds fast! avg. 3 hours 4 minutes

Price per night from

$242

Ouranos Suite

Oia villa

1 bedroom / 2 bathrooms / sleeps 5

Price per night from

$470

AQUA TERRA SUPERIOR HONEYMOON VILLA hot plunge pool and sea view

Oia house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 19 minutes

Price per night from

$383

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

Oia villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$549

Helianthus Suites/Superior Caldera Cave

Oia cave house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$762

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

Oia villa

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$370

270 Oia's View Cavehouse VII private swimming pool, sunset view

Oia villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$318

Marble Sun villa with Jacuzzi in Oia

Oia villa

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 36 minutes

Price per night from

$370

Wineryhouse where dreams live......

Oia house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 46 minutes

Price per night from

$224

Ninetta's house

Oia cottage

2 bedrooms / 1 bathroom / sleeps 4

“The Real Oia Living Experience” How wonderful it was to live at Ninetta's House for 12 days, to shop at the several supermarkets and butcher and bakeries, and cook in the little cave kitchen. To eat out on the veranda with a spectacular view of the caldera. To actually live among both seasoned year-long residents (the neighbour runs a jazz cafe) and wide-eyed tourists (our veranda became a meeting place for tourists). We did not want to leave. It was our home. Ninetta's House is simple, tasteful, and comfortable. The wireless was flawless. And she is a very gracious hostess with many tips and she helps book several of the day trips if you want to take them.

Price per night from

$229

Hector Caldera Nest

Oia private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$318

270 Oia's View House II, private swimming pool, sunset view

Oia villa

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$572

270 Oia's View Cavehouse V

Oia villa

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$377

270 Oia's View Cavehouse VI

Oia villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$358

Oia Villa Clio

Oia villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 48 minutes

Price per night from

$753

Winery Villa

Oia villa

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 40 minutes

Price per night from

$389

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

$445

SantoriniParadise: Sunset Studio

Oia house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$204

Viewing 38 of 895
rentals in Oia

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About Oia

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?