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

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165 Holiday homes

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(4) Excellent 

1 / 10

Santorini / Oia

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £111 / night

£825 - £1672 / week

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from £111 / night

(19) Excellent 

1 / 10

Rose's Cave - Oia cave house sleeps 4

Santorini / Oia

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Ask owner if suitable for children; No pets allowed;
Rose's Cave House is a spacious and cozy cave house in the village of Oia, one of the most beautiful villages of Santorini, hanging on the cliff of the caldera. The view from the courtyard is breathtaking and panoramic, which allows the eyes to wonder to the endles  …see more

from £106 / night

£673 - £1219 / week

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from £106 / night

1 / 18

PEGASUS VILLA - Oia villa sleeps 6

Santorini / Oia

2 bedroomsSleeps 61 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Great for children of all ages ; No pets allowed;
Perched on the cliffs of Perivolas, Pegasus Villa offers cave-style accommodation with arched ceilings and a furnished terrace overlooking the caldera and the volcano. Ammoudi Beach is 1.5 km away. Pegasus villa is minimally decorated with respect to the Cycladic style  …see more

from £193 / night

£1348 - £2224 / week

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from £193 / night

1 / 15

Galdera view-Godess Lethe No1 - Oia cave house sleeps 3

Santorini / Oia

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Ask owner if suitable for children; Air conditioning; Pets welcome;
It is a appartment that can accomodate 2-3 persons.The appartment has private entrance and a private terrace, a fully equiped kitchen, a bathroom with shower, one double bed and one unfolded single bed, dining room-sitting room with 2 couches and an indoor jacuzzi. It i  …see more

from £85 / night

£589 - £2648 / week

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from £85 / night

1 / 19

Santorini / Oia

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Great for children of all ages ; No pets allowed;
 …see more

from £244 / night

£0 / week

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from £244 / night

(13) Very Good 

1 / 11

Magic view of the Caldera from Thea Studios

Santorini / Oia

StudioSleeps 3Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Suitable for children age 5+;
Thea Studios is located just below the main promenade street in Oia with a stunning view of the Caldera. Surrounded by exclusive hotels we offer an affordable alternative with the same amazing view. The studios and apartments sleep 2-4 people and are simply furnished wi  …see more

from £80 / night

£503 - £1000 / week

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from £80 / night

1 / 13

Santorini / Oia

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Not suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £143 / night

£0 / week

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from £143 / night

(4) Excellent 

1 / 14

Secret Escape Private Villa with indoor jacuzzi

Santorini / Oia

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 3 km; Not suitable for children;
White Pearl Villas in Oia, Santorini, carved in the volcanic rocks of Theran land with the mystical beauty of the caldera cliff, stretching before them, open their doors to take you on a magic trip. Built on the edge of the cliff through the centuries, restored with res  …see more

from £269 / night

£0 / week

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from £269 / night

1 / 13

Santorini / Oia

1 bedroomSleeps 52 nights min stay

  • 1 bedroom
  • Sleeps 5
  • 2 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Car advised;
 …see more

from £253 / night

£0 / week

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from £253 / night

(1) Excellent 

1 / 18

Santorini / Oia

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Ask owner if suitable for children; Air conditioning; Some pets are welcome - please contact the owner;
 …see more

from £311 / night

£0 / week

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from £311 / night

(3) Excellent 

1 / 20

Santorini / Oia

2 bedroomsSleeps 62 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
 …see more

from £118 / night

£715 - £2009 / week

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from £118 / night

1 / 30

CASA SIGALA OIA SANTORINI - Oia cave house sleeps 5

Santorini / Oia

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Great for children of all ages ; Air conditioning;
Casa Sigala is located in the picturesque Oia and close to the Venetian, medieval castle of Oia, the "Castle of St. Nicholas." It is a traditional cave house, built in early 1800, fully restored and offering panoramic views of the Aegean Sea and the sunset. It has 2 bed  …see more

from £152 / night

£925 - £1816 / week

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from £152 / night

(5) Excellent 

1 / 29

Santorini / Oia

3 bedroomsSleeps 51 night min stay

  • 3 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 3 km; Not suitable for children;
 …see more

from £295 / night

£2059 - £2942 / week

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from £295 / night

(1) Excellent 

1 / 20

Pina Caldera Residence with Pool - Oia villa sleeps 2

Santorini / Oia

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Ask owner if suitable for children; Pets welcome;
With its breath-taking views over the Oia cliffs, the Pina Caldera Residence is a stunning hideaway for any visitor to the beautiful island of Santorini. The pine tree in the property’s garden is a rare sight on the island and signals exclusivity with characterful cha  …see more

from £337 / night

£0 / week

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from £337 / night

1 / 11

Santorini / Oia

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £101 / night

£589 / week

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from £101 / night

1 / 12

VillaAlkmini 14 sq. m. with a sea view! - Oia apartment sleeps 2

Santorini / Oia

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Great for children of all ages ; Air conditioning; Pets welcome;
Only 2000 meters from the world-renowned village of Oia and just a few steps from its beautiful black sandy beach. It is the ideal place to stay for those wishing to relax in a beautiful and friendly ambience. Villa Alkmini has been built according to the traditional a  …see more

from £36 / night

£0 / week

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from £36 / night

1 / 15

Santorini / Oia

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Ask owner if suitable for children; Air conditioning; No pets allowed;
 …see more

from £101 / night

£631 - £1295 / week

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from £101 / night

1 / 68

Santorini / Oia

3 bedroomsSleeps 10Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 1 km; Swimming pool; Suitable for children age 5+;
 …see more

from £337 / night

£2353 - £3336 / week

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from £337 / night

(6) Excellent 

1 / 37

House of the singing birds - Oia house sleeps 2

Santorini / Oia

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Not suitable for children;
The House of the Birds (Guest house on the oriental garden)part of the "Winery Villa" complex: This small house is and Independent Studio of 30 sq. m. in three levels. It is including bedroom with “antique” style double bed, sizable bathroom, kitchenette with separ  …see more

from £79 / night

£548 - £665 / week

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from £79 / night

1 / 7

Santorini / Oia

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Air conditioning; No pets allowed;
 …see more

from £466 / night

£3259 - £4236 / week

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from £466 / night

1 / 9

Aspa Caves - Traditional exclusive studio.

Santorini / Oia

StudioSleeps 22 nights min stay

  • Studio
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 1 km; Not suitable for children; Car not necessary;
Traditional exclusive cave studioThis is a unique accommodation proposal. Nested within the historical heart of Oia's village, the cave studio is built within the volcanic rock according to the traditional island's architecture which is adapted to Santorini�  …see more

from £135 / night

£1471 / week

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from £135 / night

(7) Excellent 

1 / 38

Sunny Winehouse - Oia house sleeps 2

Santorini / Oia

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Not suitable for children;
The Sunny Winehouse, (Studio apartment on the terrace): This is a small house built in the traditional Santorinial way, on the top of an old winery (“Winery house”). Although connected to the winery's court via step stone stairs, this house has an independent entr  …see more

from £97 / night

£677 - £853 / week

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from £97 / night

1 / 5

Santorini / Oia

StudioSleeps 2Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £127 / night

£883 - £1177 / week

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from £127 / night

1 / 7

Mystic Luxury Villa II with Sea View & Jacuzzi

Santorini / Oia

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 3 km; Ask owner if suitable for children;
White Pearl Villas in Oia, Santorini, carved in the volcanic rocks of Theran land with the mystical beauty of the caldera cliff, stretching before them, open their doors to take you on a magic trip. Built on the edge of the cliff through the centuries, restored with res  …see more

from £169 / night

£2118 - £2471 / week

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from £169 / night

(6) Excellent 

1 / 17

Santorini / Oia

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 1 km; Suitable for children age 5+; Air conditioning;
 …see more

from £135 / night

£942 - £1824 / week

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from £135 / night

(7) Excellent 

1 / 64

Wineryhouse and 2 guest houses - Oia villa sleeps 10

Santorini / Oia

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Swimming pool;
The main house and each one of the 2 independent guesthouses can be rented all together (for families or groups of friends), but also as individual units. This Old winery building complex, is restored to a luxury villa, consisting on 3 houses. It is located on the nort  …see more

from £337 / night

£2353 - £3336 / week

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from £337 / night

1 / 34

Santorini / Oia

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 1 km; Great for children of all ages ; Car advised;
 …see more

from £201 / night

£0 / week

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from £201 / night

(3) Very Good 

1 / 23

The sunset windmill - Oia house sleeps 6

Santorini / Oia

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Great for children of all ages ;
A traditional Aegean island windmill has been transformed into a fully equipped 74 sq. mt. house with modern facilities. The mill has an attic where children love to sleep and a private yard ideal for breakfast or night cocktails with guests. Guests have access to the c  …see more

from £152 / night

£841 - £1051 / week

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from £152 / night

1 / 14

"Oia Cave Houses" Love House - Oia house sleeps 5

Santorini / Oia

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Ask owner if suitable for children; Air conditioning; Some pets are welcome - please contact the owner;
Nestled on the cliffs of the worldwide famous village of Oia, Oia Cave Houses welcome you to the beautiful island of Santorini. Gazing the deep blue, Oia Cave Houses is a cluster of four traditional cave houses ideal for all visitors’ who wish to experience a traditio  …see more

from £194 / night

£1345 - £3118 / week

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from £194 / night

(10) Excellent 

1 / 29

Fava Eco Residences - Aeolos Suite - Oia apartment sleeps 3

Santorini / Oia

2 bedroomsSleeps 31 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Great for children of all ages ;
Welcome home to Fava! An unforgettable experience. Our goal is to make you feel that Fava is your own home and Santorini, your island. The Fava Eco-Residences are housed in a group of splendid and unique captain houses of the mid 19th century, located at the highest poi  …see more

from £118 / night

£742 - £1342 / week

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from £118 / night

(4) Excellent 

1 / 8

Santorini / Oia

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £211 / night

£3236 / week

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from £211 / night

(12) Excellent 

1 / 51

Wineryhouse, where dreams live - Oia house sleeps 6

Santorini / Oia

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Swimming pool;
An old Winery renovated and transformed into a very stylish villa with amazing oriental garden and a tiny swimming pool Situated in the peaceful and traditional village of "Finikia" in Oia The Winery House (main domain), part of the "Winery Villa" complex: This was th  …see more

from £174 / night

£1218 - £1818 / week

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from £174 / night

1 / 39

Santorini / Oia

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 0 km; Ask owner if suitable for children; Car advised;
 …see more

from £406 / night

£2836 - £3865 / week

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from £406 / night

1 / 10

Santorini / Oia

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Ask owner if suitable for children; Car not necessary;
 …see more

from £202 / night

£1412 - £2471 / week

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from £202 / night

1 / 10

Mystic Luxury Villa I, Caldera View & Jacuzzi

Santorini / Oia

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
White Pearl Villas in Oia, Santorini, carved in the volcanic rocks of Theran land with the mystical beauty of the caldera cliff, stretching before them, open their doors to take you on a magic trip. Built on the edge of the cliff through the centuries, restored with res  …see more

from £169 / night

£1177 - £2471 / week

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from £169 / night

(1) Excellent 

1 / 36

Santorini / Oia

3 bedroomsSleeps 91 night min stay

  • 3 bedrooms
  • Sleeps 9
  • 1 night min stay
Key info: Ask owner if suitable for children; Air conditioning; Some pets are welcome - please contact the owner;
 …see more

from £337 / night

£2353 - £8077 / week

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from £337 / night

(10) Excellent 

1 / 10

caldera view- goddess lethe no2 - Oia cave house sleeps 3

Santorini / Oia

1 bedroomSleeps 32 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Not suitable for children; Air conditioning; No pets allowed;
It is an appartment that can accomodate 2-3 persons.The appartment has private entrance and a private terrace, a fully equiped kitchen, a bathroom with shower, one double bed and one unfolded single bed, dining - sitting room with couch and an outdoor jacuzzi.It is a ca  …see more

from £110 / night

£2059 - £2648 / week

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from £110 / night

1 / 28

Santorini / Oia

4 bedroomsSleeps 72 nights min stay

  • 4 bedrooms
  • Sleeps 7
  • 2 nights min stay
Key info: Suitable for children age 5+; Air conditioning; Some pets are welcome - please contact the owner;
 …see more

from £290 / night

£2030 - £6824 / week

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from £290 / night

(1) Excellent 

1 / 22

Poseidon Mansion in Santorini - Oia villa sleeps 8

Santorini / Oia

4 bedroomsSleeps 82 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Great for children of all ages ; Air conditioning; Some pets are welcome - please contact the owner;
Poseidon Mansion occupies a privileged location in Santorini. It is a cultural heritage building known from the old years as Captain's house and dates back to 1890.Poseidon Mansion is nestled on the famous cliffs of Oia in Santorini, gazing the beauty of the infinity Ae  …see more

from £290 / night

£2030 - £7412 / week

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from £290 / night

1 / 18

Santorini / Oia

1 bedroomSleeps 51 night min stay

  • 1 bedroom
  • Sleeps 5
  • 1 night min stay
Key info: Great for children of all ages ; No pets allowed;
 …see more

from £311 / night

£0 / week

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from £311 / night

Top Destination reviews

Magic view of the Caldera from Thea Studios
Amazing View with the best access to the pedestrian street.

This rental is awesome. The views are amazing, with the location being just as good. You can walk out your own private entrance from the pedestrian street and within 20 meters find the boat tour counter, a market, 3 restaurants and car/motorbike rent … see more
OIA SUNSET VILLAS - villa DIAMOND - Pool & 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 … see more
Wineryhouse and 2 guest houses
Exactly what we needed

The place is a gem. The owners are great as not only they rented us a place with perfect condition, but also helped us organize our stay in Santorini. They suggested great places to visit and great restaurants, all with a human and very friendly touc … see more
Fava Eco Residences - Helios Suite
Most Beautiful Villa with an amazing view

We stayed in Fava for 4 full days and couldn't be happier. A 10 minute walk from Oia - this beautiful cave house came equipped with everything. The location was awesome as it was next to great restaurants, local shops and even bus stops. I would defi … see more
Lava Cave with outdoor Hot Tub and Panoramic View
Magnificent view-Impeccable service!

This holiday house was exceptional and we spent the most unfogettable vacations! Breathtaking view, great amenities and super service! The jacuzzi was like a cave, always so clean and we took so many pictures of and in it! Our friends saw it via skyp … see more
Fava Eco Residences - Anemos Suite
Santorini

This place is a hike to get to. The place was very nice and we were able to sleep 3 people. 2 people upstairs and one downstairs. You could have fit a 4th person on the couch downstairs. The place was very clean. The drawback was that we were … see more

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