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Vacation Rentals & Villas in Oia

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936 villas

SantoriniParadise: 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 been updated and looked great. We were welcomed with fresh fruit, eggs, water, wine and snacks. Maria was so helpful and attentive and spent time with each group giving suggestions on things to do and places to go. The sunset view from the rooftop patio of the Helios house is out of this world. Maria brought us drinks and appetizers the first night to watch it. There we hundreds of people around us watching and we had the best seats. Maria asked for constructive feedback from us, which we had very little to give. I appreciate an owner always trying to improve the experience of her guests. It says a lot about Maria's commitment to her guests. We highly recommend Maria and any of her places.

Price per night from

$272

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

$399

SantoriniParadise: 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

Price per night from

$258

The House of the Seven Ships

Oia house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 35 minutes

Price per night from

$163

SantoriniParadise: HELIOS cave house, amazing sunset view

Oia house

1 bedroom / 1 bathroom / sleeps 5

“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 been updated and looked great. We were welcomed with fresh fruit, eggs, water, wine and snacks. Maria was so helpful and attentive and spent time with each group giving suggestions on things to do and places to go. The sunset view from the rooftop patio of the Helios house is out of this world. Maria brought us drinks and appetizers the first night to watch it. There we hundreds of people around us watching and we had the best seats. Maria asked for constructive feedback from us, which we had very little to give. I appreciate an owner always trying to improve the experience of her guests. It says a lot about Maria's commitment to her guests. We highly recommend Maria and any of her places.

Price per night from

$273

BLUEDOME CAVEHOUSE OIA SANTORINI

Oia villa

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,004

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

Responds fast! avg. 1 hour 37 minutes

Price per night from

$868

Big Blue villa in Oia

Oia house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$227

“Paradise of the paradise!” The stay in this apt was a great experience. The staff was really nice and came by everyday for laundry. The view from the balcony was perfect for the sunset in Oia. The location was 5 min walk from the Duomo plaza but very quite and cozy. The decoration in the house was beautiful and very comfortable. My friends and I love it very much!

Price per night from

$271

Hector Cave house

Oia cave house

1 bedroom / 2 bathrooms / sleeps 5

Price per night from

$529

Oia White - stunning Caldera views in Oia village

Oia villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$385

Helianthus Suites/Superior Caldera Cave

Oia cave house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$850

"The Annouso" villa in Oia

Oia house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$197

Wineryhouse where dreams live......

Oia house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 35 minutes

Price per night from

$238

Astrea Suites: Ostria Cave House - Outdoor Jacuzzi

Oia villa

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$367

Hector Caldera Nest

Oia private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$339

Kristy Cave House

Oia house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$510

The House of the Singing Birds

Oia house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 35 minutes

Price per night from

$123

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

Oia villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$719

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

Oia villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,467

Marble Sun villa with Jacuzzi in Oia

Oia villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$264

SiskosPlace Elias Cottage, Oia Santorini

Oia cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 38 minutes

Price per night from

$199

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

Oia villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$461

270 Oia's View Cavehouse V

Oia villa

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$394

AQUA TERRA SUPERIOR PRIVATE VILLA hot plunge pool and sea view

Oia house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$407

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

Oia villa

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$720

270 Oia's View Cavehouse VI

Oia villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$394

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!

Price per night from

$385

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

Oia villa

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$461

Winery Villa

Oia villa

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 35 minutes

Price per night from

$368

Hector Luxury Cave

Oia house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$529

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

$496

The Sunny Winehouse

Oia house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 35 minutes

Price per night from

$150

The Red Winehouse

Oia villa

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 35 minutes

Price per night from

$204

Oia Waves Cavehouses complex, caldera view, low winter rates

Oia house

3 bedrooms / 3 bathrooms / sleeps 10

“wonderful experience” We are delighted with the house, is spectacular, the view, the location, the privacy. It offers a unique space to enjoy with great serenity. Anastasia, the owner, is a very warm person and very willing to help, with incredible hospitality, she was aleways in contact with us since we start the arrangements, coaching our trip; she offers many facilities with the flights, and she quickly resolved any questions or need we had. A family and a house absolutely recommendable and enjoyable, I hope we can come back and so our friends and familiy.

Responds fast! avg. 3 hours 16 minutes

Price per night from

$82

Wineryhouse and two guest houses

Oia villa

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 35 minutes

Price per night from

$551

Astrea Suites: Fisherman's Nest -Oia- Ammoudi Bay

Oia house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$258

SantoriniParadise: Sunset Studio

Oia house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$259

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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?

Top Destination reviews

SantoriniParadise: BLUE & WHITE Cave House, Santorini, Oia + hot tub!
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 provided with fresh options delivered each morning,without endlessly, wandering, visitors.The hot tub, a short walk, affords an almost secluded sunset view and is available every other day.If you ask in the morning it will be toasty when you arrive.We were met by the charming Sergio who never failed to provide an escort,an answer,a suggestion.He is Maria's man of all trades,who even helped with the daily maid service as she did not speak English.His recommendation,the Candouni family run restaurant,was a gift.We ate there every night...it's that good.Thank you Maria for a once in a lifetime visit to paradise.see more
AMBROSIA VILLA
Lovely stay in villa ambrosia Oiaa

Maria is a warm and very obliging hostess. The little tub of water outside the villa was not functioning and it is a little tedious to walk up the staircase every time you forget something . The villa is comfortable and CLEAN We had a lovely stay and Maria is very nice … see more
SantoriniParadise: SUNSET APARTMENT, panoramic Sunset view from terrace!
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!!see more
Villa Kallisti
Amazing views, Perfect apartment!

Three other friends and I stayed at Villa Kallisti this past weekend, and it was absolutely perfect. Maria responded to emails quickly and even set up a taxi to pick us up from the airport and ferry port. Everything went smoothly and the porter was waiting for my taxi when I arrived in Oia. The views from the terrace were like something out of a postcard! The apartment was spotless and the wifi was strong. We stayed there for two nights and had everything we needed. If you are going to Oia, then I would definitely stay here!!see more
SantoriniParadise: HELIOS cave house, amazing sunset view
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 absolutely amazing; front and centre for the sunsets in Oia, which are a must see event on the island. (We couldn't help but feel smug when surrounded by all the other travellers trying to find a spot to watch the sunset while we had the terrace and comfortable seating to enjoy!) It was an amazing first impression of Oia. The cave house itself is very comfortable and well equipped. The kitchen was rather small, but for our purposes (coffee and eggs in the morning) it was fine. Maria was an excellent host who genuinely cares about her guests experiences and is available to give recommendations on where to eat and advice on what to do. We would highly recommend the Helios cave house - when the time came I didn't want to leave! A wonderful getaway. :)see more
SantoriniParadise: PARADISE, outdoor Hot Tub, Caldera panorama!
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 . … see more

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