Vacation Rentals & Villas in Oia

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621 villas

SantoriniParadise: 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

Price per night from

$275

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

$611

“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

$237

SantoriniParadise: HELIOS cave house, amazing sunset view

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!!

Price per night from

$268

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. 58 minutes

Price per night from

$748

BLUEDOME CAVEHOUSE OIA SANTORINI

Oia villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$923

“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

$212

"The Annouso" villa with Hot Tub in Oia

Oia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$349

Big Blue villa in Oia

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$462

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

Oia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,060

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

Oia villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$611

Helianthus Suites/Superior Caldera Cave

Oia cave house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$748

SiskosPlace Elias Cottage, Oia Santorini

Oia cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$175

AQUA TERRA SUPERIOR PRIVATE VILLA hot plunge pool and sea view

Oia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 2 hours 33 minutes

Price per night from

$998

270 Oia's View Cavehouse VI

Oia villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$487

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

Oia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,160

Marble Sun villa with Jacuzzi in Oia

Oia villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$374

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

Oia villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$935

SantoriniParadise: Sunset Studio

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$212

Blue Sky Cave House Oia Caldera

Oia cave house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$406

The 'Top Caldera view' villa in Oia

Oia villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$462

Bluedome Suite

Oia villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

Price per night from

$487

Daphne House

Oia house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$741

Apanema Cavehouse

Oia cave house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Price per night from

$611

SiskosPlace Alexandros Cottage, Oia Santorini

Oia cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$412

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

Oia villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$736

Aqua & Terra loft house with caldera view and hot plunge pool

Oia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 33 minutes

Price per night from

$748

AVAX VILLA by K&K

Oia villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$2,222

Volcano Suite

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$599

Measure

Oia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$817

Caldera Suite

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$599

The White cavehouse in Oia

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$349

Palea

Oia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$1,378

“Santorini Sensation @ Grand Canava” Lost in the captivating whites of the island, Grand Canava offered an unforgettable stay, we awoke on the beautiful scenery overlooking the volcano with the delicious aromas of traditional greek home-made breakfast and enjoyed the warm welcome of our lovely host Roxanne and her team. She made sure to make us feel right at home, this made saying our goodbyes a little harder. Grand Canava was equipped with all amenities necessary, the rooms have a lovely traditional feel, some cycladic and some rustic chic, each had their own character and flavor to them. The staff made sure they did their very best to accommodate our needs and provide us with the support to book our leisure activities and reserve in best dinner spots. A definite unforgettable stay, that we will repeat in the near future.

Price per night from

$2,494

Villa Nea

Oia house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$1,198

Ftelari Villa

Oia villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$1,746

ARCHON VILLA by K&K

Oia villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$1,852

"3 Caves Suite" with hot tub in Oia

Oia villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$487

Viewing 38 of 621
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
SantoriniParadise: SUNSET APARTMENT, panoramic Sunset view from rooftop 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
270 Oia's View House I, private swimming pool, sunset view
Serene, beautiful, comfortable

After doing a lot of research on Santorini Island and looking at photos of rentals there, 270View stuck out because it seemed to be in a nice spot. As another reviewer mentioned, there are four units side-by-side. House 4 gives you the best views because it's highest us. Manny is an architect and has built the building into the hill, incorporating some of the natural rock inside. It's very cool and pleasantly cave-like in the bedroom, and airy in the kitchen and dining room area. The decor is very minimalistic, white wood, glass, and stainless steel. The view from the pool area is gorgeous. To see the caldera, you have to hike up the hill a short way, but it's worth it. The place is spotlessly maintained, with daily cleaning service. We were lucky that Manny was there to greet us when we arrived, because in addition to the other little amenities that are listed in the property description, the owner is a great source of information about where to go and what to do in Santorini. We went during early October of 2012, in what is called the "shoulder" season. It really made a difference, because the temperatures were still quite warm, but there weren't the crowds associated with the high season. Still, busloads of tourists passed by on the road below every day, going for a short visit to Oia for sunset and then back to the cruise ship. You should visit Sigalas winery if you have a car or scooter, you should go there and sample their wines. The "Crisis" is a great table wine and the assyrtiko/athiri blend is amazing. One other "amenity" that came with 270View house: Like a lot of places in Greece, the house was the territory of a particular cat. Ours was a calico who came in to see us after we go settled into the place. She always was there to see us when we got up in the morning and when we came back from being out at night, and especially when we had anything to eat! It was nice to sort of be "adopted" by a local.see more
SantoriniParadise: PARADISE, outdoor Hot Tub, Caldera panorama!
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.see more
SantoriniParadise: HELIOS cave house, amazing sunset view
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.see more
Unique Restored 1868 Wine Canava - Caldera View, Private Pool, Sunbathing Deck
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 conveniently near. Roxanne and her staff were helpful and friendly. … see more

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