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Villas in Oia and Apartments - Holiday Lettings - Holiday Rentals Oia

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114 Holiday homes

Oia holiday villa rental

Oia villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Amazing honeymoon in Paradise” We stayed here in in the last week of March, and the place was amazing. The villa was well maintained and very cleaned. It is at very peaceful location with an amazing view. We contacted Maria few weeks back prior to our arrival, and she gave all useful information about the area and the surroundings. Her information was very specific to our needs. Our housekeeper was very friendly, she did our laundry as well. We had a perfect stay! I guess our villa was at the best location in Oia. The villa was a perfectly magical for our honeymoon. Thank you so much Maria for all your services.

from £198 / night

£1,384 / week

1 / 74

Holiday home with swimming pool in Oia

Oia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £178 / night

£1,246 / week

1 / 50

Oia holiday cave house rental

Oia cave house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £297 / night

£1,088 / week

1 / 14

Holiday home in Oia

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 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. :)

from £228 / night

£1,592 / week

1 / 91

Holiday home in Oia

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £248 / night

£1,730 / week

1 / 4

Holiday home in Oia

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £119 / night

£831 / week

1 / 34

Holiday villa with swimming pool in Oia

Oia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £534 / night

£3,737 / week

1 / 68

Holiday villa with swimming pool in Oia

Oia villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £445 / night

£3,115 / week

1 / 46

Holiday villa in Oia

Oia villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £537 / night

£3,759 - £5,805 / week

1 / 34

Home rental in Oia

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £119 / night

£831 / week

1 / 37

Holiday villa in Oia

Oia villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £1,280 / night

£4,924 / week

1 / 28

Cave house rental in Oia

Oia cave house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £594 / night

£4,153 / week

1 / 16

Holiday apartment rental

Oia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £414 / night

£2,895 / week

1 / 8

Holiday apartment in Oia

Oia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £414 / night

£2,895 / week

1 / 6

Holiday apartment rental

Oia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £97 / night

£680 / week

1 / 17

Oia holiday home rental

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £129 / night

£902 / week

1 / 36

Holiday home rental

Oia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £591 / night

£4,136 - £5,934 / week

1 / 32

Holiday home in Oia

Oia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £583 / night

£4,076 - £5,934 / week

1 / 32

Home rental in Oia

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £158 / night

£1,103 / week

1 / 20

Holiday home rental

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £403 / night

£2,817 - £3,956 / week

1 / 28

Holiday home rental

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £403 / night

£2,817 - £3,956 / week

1 / 26

Holiday villa rental

Oia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £514 / night

£3,599 / week

1 / 63

Holiday home in Oia

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £522 / night

£3,653 / week

1 / 11

Holiday home in Oia

Oia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £594 / night

£4,153 / week

1 / 67

Oia holiday cave house rental

Oia cave house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £275 / night

£1,924 / week

1 / 20

Holiday home accommodation

Oia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £925 / night

£6,474 - £10,489 / week

1 / 39

Oia holiday cave house let

Oia cave house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £296 / night

£2,068 / week

1 / 51

Holiday villa in Oia

Oia villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £365 / night

£2,551 / week

1 / 29

Holiday home in Oia

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £276 / night

£1,930 / week

1 / 17

Holiday studio in Oia

Oia studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £148 / night

£1,034 / week

1 / 10

Holiday home in Oia

Oia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £197 / night

£1,379 / week

1 / 31

Holiday cave house letting

Oia cave house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £168 / night

£1,177 / week

1 / 26

Holiday home with swimming pool in Oia

Oia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £887 / night

£6,204 / week

1 / 18

Oia holiday home rental

Oia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £139 / night

£969 / week

1 / 30

Holiday villa in Oia

Oia villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £129 / night

£851 - £1,266 / week

1 / 24

Holiday villa in Oia

Oia villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £791 / night

£5,537 / week

1 / 12

Oia holiday villa rental

Oia villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £791 / night

£5,537 / week

1 / 12

Oia holiday home rental

Oia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £434 / night

£3,033 / week

1 / 9

Holiday guest house in Oia

Oia guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £404 / night

£2,826 / week

1 / 22

Oia holiday villa rental

Oia villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £1,755 / night

£12,283 / week

1 / 44

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Oia holidays

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 holiday rentals in Oia to choose from on Holiday Lettings, 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 harbour 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 jewellery – 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 flavours 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 Holiday Lettings apartment or villa – why not search for your perfect holiday rental, today?

Top Destination reviews

Wineryhouse where dreams live......
Out of this world. Stunning location, stylish peaceful property

"A very peaceful and relaxing place in a traditional Greek village, attached to busy Oia. The house is absolutely amazing in architecture and style. You can enjoy the local wines in the corners of the sizable garden or watch the sunset from the terrace. We really enjoyed our stay in this wonderful place. Oia is in walking distance from the house. The owners were very helpful. They revealed all the "hidden" places on the island and helped us organize our tours around the island in the best possible way. We look forward to returning there some day and make our dreams come true once again.see more
OIA SUNSET VILLAS - villa DIAMOND - Pools & Spa
Great Location & personal service

Complex of 5 villas with shared pool, 1 villa with private pool & extended grounds.. great location 5 mins from Oia..fabulous sunsets! Lovely villas, only downside shower rooms are really small! Site Manager Konstantinos will do anything you ask, no job too small, will also book cabs, get shopping/food deliveries, book trips/restaurants etc.see more
OIA SUNSET VILLAS - villa "EMERALD" - Pools & Spa
Everything we could hope for!

Sunset Villas offered everything we needed for our family holiday. The location is beautiful and lives up to the description and photographs. There was plenty to do locally with Oia and Ammoudi Bay just a short walk away. … see more

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