Vacation Rentals & Villas in Oia

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926 villas

(47) Excellent 

43

SantoriniParadise: PARADISE, outdoor Hot Tub, Caldera panorama!

Santorini / Oia

Oia villa

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly
“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
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Price per night from

$206

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$206

(3) Excellent 

25

Villa Amalia sleeps 9 by Thireon

Santorini / Oia

Oia cave house

4 9 2 nights min

  • 4 bedrooms
  • sleeps 9
  • 2 nights min

Price per night from

$679

Price per night from

$679

(3) Very Good 

29

Skala Traditional Cave +outdoor Jacuzzi by Thireon

Santorini / Oia

Oia cave house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Suitable for children age 5+

Price per night from

$912

Price per night from

$912

(30) Excellent 

42

SantoriniParadise: PINK Cave, 3 terraces outdoor jacuzzi Caldera View

Santorini / Oia

Oia villa

3 4 1 night min

  • 3 bedrooms
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary
“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!
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Price per night from

$263

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$263

(26) Excellent 

66

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

Santorini / Oia

Oia villa

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Child Friendly
“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 provid
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Price per night from

$204

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$204

(13) Excellent 

14

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

Santorini / Oia

Oia villa

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning
“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 cam
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Price per night from

$399

Price per night from

$399

40

Ramni House with Pool and Beach by Thireon

Santorini / Oia

Oia villa

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Price per night from

$1,083

Price per night from

$1,083

30

The House of the Seven Ships

Santorini / Oia

Oia house

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$149

Responds fast!
avg. 1 hour 47 minutes

Price per night from

$149

10

HELIOS EXCLUSIVE POOL VILLA

Santorini / Oia

Oia villa

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$855

Price per night from

$855

(20) Excellent 

71

SantoriniParadise: HELIOS or SISTERHOOD of traveling pants + hot tub

Santorini / Oia

Oia house

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly
“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 absolute
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Price per night from

$227

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$227

(7) Excellent 

24

BLUEDOME CAVEHOUSE OIA SANTORINI

Santorini / Oia

Oia villa

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$725

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$725

(1) Excellent 

19

CanavaView at Sunset with Jacuzzi by Thireon

Santorini / Oia

Oia cave house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Air conditioning

Price per night from

$741

Price per night from

$741

(13) Very Good 

46

Luxury Villa at Oia with amazing view and pool

Santorini / Oia

Oia villa

3 9 3 nights min

  • 3 bedrooms
  • sleeps 9
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“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 o
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Price per night from

$662

Price per night from

$662

21

Big Blue villa in Oia

Santorini / Oia

Oia house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly

Price per night from

$285

Price per night from

$285

(2) Excellent 

23

Ammos Oia Mansion

Santorini / Oia

Oia villa

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$627

Price per night from

$627

(17) Very Good 

36

SantoriniParadise: SUNSET TERRACE, cave house , panoramic Sunset view !

Santorini / Oia

Oia house

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly
“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
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Price per night from

$228

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$228

(3) Excellent 

33

Oia White - stunning Caldera views in Oia village

Santorini / Oia

Oia villa

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Air conditioning

Price per night from

$210

Responds fast!
avg. 3 hours 50 minutes

Price per night from

$210

(7) Very Good 

24

"The Annouso" villa in Oia

Santorini / Oia

Oia house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$227

Price per night from

$227

(26) Excellent 

76

Ilivatos Oia .. The house of your private escape

Santorini / Oia

Oia house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning
“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 !
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Price per night from

$906

Price per night from

$906

(7) Excellent 

19

Hector Cave house

Santorini / Oia

Oia cave house

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$456

Price per night from

$456

(8) Excellent 

Certificate of Excellence

29

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

Santorini / Oia

Oia villa

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Air conditioning

Certificate of Excellence

Price per night from

$317

Price per night from

$317

37

The House of the Singing Birds

Santorini / Oia

Oia house

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Car not necessary

Price per night from

$108

Responds fast!
avg. 1 hour 47 minutes

Price per night from

$108

(2) Excellent 

35

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

Santorini / Oia

Oia villa

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$662

Price per night from

$662

(18) Excellent 

48

Wineryhouse where dreams live......

Santorini / Oia

Oia house

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$198

Responds fast!
avg. 1 hour 47 minutes

Price per night from

$198

16

Helianthus Suites/Superior Caldera Cave

Santorini / Oia

Oia cave house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$305

Price per night from

$305

18

Ouranos Suite

Santorini / Oia

Oia villa

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Child Friendly

Price per night from

$422

Price per night from

$422

(12) Excellent 

22

Kristy Cave House

Santorini / Oia

Oia house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$399

Responds fast!
avg. 2 hours 8 minutes

Price per night from

$399

(2) Excellent 

13

SiskosPlace Elias Cottage, Oia Santorini

Santorini / Oia

Oia cottage

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Ask about pets

Price per night from

$159

Responds fast!
avg. 2 hours 9 minutes

Price per night from

$159

(8) Excellent 

26

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

Santorini / Oia

Oia villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$487

Price per night from

$487

(11) Excellent 

17

Ninetta's house

Santorini / Oia

Oia cottage

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Nearest beach 1 mi
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$204

Price per night from

$204

(30) Excellent 

Certificate of Excellence

36

Oia Blue - sleek interiors in majestic setting

Santorini / Oia

Oia villa

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning
“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 bustl
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Certificate of Excellence

Price per night from

$210

Responds fast!
avg. 3 hours 50 minutes

Price per night from

$210

16

Amaya: The Windmill Villa

Santorini / Oia

Oia villa

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$354

Price per night from

$354

(1) Excellent 

21

Opuntia Traditional Cave at Blue Dome by Thireon

Santorini / Oia

Oia cave house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$736

Price per night from

$736

(4) Very Good 

12

Hector Caldera Nest

Santorini / Oia

Oia room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$228

Price per night from

$228

(7) Excellent 

30

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

Santorini / Oia

Oia villa

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$283

Price per night from

$283

(16) Excellent 

78

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

Santorini / Oia

Oia house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$283

Responds fast!
avg. 2 hours 51 minutes

Price per night from

$283

11

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

Santorini / Oia

Oia villa

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$331

Price per night from

$331

(1) Excellent 

27

Oia Villa Clio

Santorini / Oia

Oia villa

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$673

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$673

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?