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

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168 Holiday homes

(45) Very Good 

11

Magic view of the Caldera from Thea Studios - Oia studio sleeps 3

Santorini / Oia

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • 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 £83 / night

£520 - £761 / week

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from £83 / night

(20) Excellent 

10

Rose's Cave - Oia cave house sleeps 4

Santorini / Oia

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
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 £109 / night

£696 - £1261 / week

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from £109 / night

18

PEGASUS VILLA - Oia villa sleeps 6

Santorini / Oia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
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 £200 / night

£1394 - £2301 / week

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from £200 / night

(4) Excellent 

14

Secret Escape Private Villa with indoor jacuzzi - Oia cave house sleeps 4

Santorini / Oia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Car not necessary
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 £279 / night

£1948 / week

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from £279 / night

15

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

Santorini / Oia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly
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 £87 / night

£609 - £2435 / week

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from £87 / night

(1) Very Good 

19

Absolut peace north villa - Oia villa sleeps 4

Santorini / Oia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.5 km
  • Child friendly
  • Air conditioning
Quiet and spacious, laid out on two levels, our home is the ideal accommodation for a couple or a family of four.The upper level has the master bath and bedroom as well as a balcony to watch your most memorable sunrises from. The ground level consists of a living room w  …see more

from £70 / night

£487 - £696 / week

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from £70 / night

(10) Excellent 

10

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

Santorini / Oia

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Air conditioning
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 £114 / night

£792 / week

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from £114 / night

9

Aspa Caves - Traditional exclusive studio. - Oia studio sleeps 2

Santorini / Oia

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 1 km
  • Car not necessary
  • Air conditioning
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 £140 / night

£1522 / week

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from £140 / night

12

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

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
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 £37 / night

£256 / week

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from £37 / night

(3) Very Good 

30

CASA SIGALA OIA SANTORINI - Oia cave house sleeps 5

Santorini / Oia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • 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 £157 / night

£957 - £1748 / week

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from £157 / night

(5) Excellent 

26

The house of the seven ships - Oia house sleeps 4

Santorini / Oia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 1 km
  • Ask owner if suitable for children
  • Ask about pets
This is a 60 sq m house, with panoramic views over the Aegean Sea and the vineyards of Finikia from the terrace-balcony of 30 sq. m House is composed by the main domed chamber (living-dining room), one domed bedroom, sizeable bathroom and a fully equipped kitchen. The  …see more

from £100 / night

£700 - £1005 / week

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from £100 / night

19

Santorini / Oia

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £200 / night

£1400 / week

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from £200 / night

13

Santorini / Oia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask about pets

 …see more

from £148 / night

£1035 / week

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from £148 / night

9

Aegean Magic Villa Private Jacuzzi & Sea View - Oia villa sleeps 2

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask owner if suitable for children
  • 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 £244 / night

£2374 - £3287 / week

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from £244 / night

10

Azalea Houses Suite - Finikia Traditional Houses - Oia cave house sleeps 2

Santorini / Oia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Air conditioning
Located in Finikia, within a 20-minute walk from the the scenic Oia, the 18th-century Azalea Houses offers elegantly decorated suites overlooking the Aegean Sea and the village. Equiped with a double bed is perfect for a couple in romantic holidays.The SpaceThe house wa  …see more

from £109 / night

£761 - £914 / week

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from £109 / night

(6) Excellent 

13

Full Moon Villa, jacuzzi, volcano & sea view - Oia cave house sleeps 2

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Child friendly
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 £240 / night

£2265 - £2849 / week

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from £240 / night

27

"Oia Cave Houses" Joy House with caldera view - Oia house sleeps 3

Santorini / Oia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
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 £166 / night

£1157 - £1948 / week

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from £166 / night

(1) Excellent 

17

Lava Cave with outdoor Hot Tub and Panoramic View - Oia cave house sleeps 3

Santorini / Oia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Live the myth by staying in a cave that used to be a sailor’s domicile back in 1875. Today after a full restoration, it has been turned into a jewel, keeping its traditional cave-curved Aegean island style with its pearl white walls. The suite is luminous, with a cozy  …see more

from £218 / night

£1522 - £2314 / week

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from £218 / night

(1) Excellent 

38

OIA SUNSET VILLAS - villa "TURQUOISE" - Pool & Spa - Oia villa sleeps 6

Santorini / Oia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Villa "TURQUOISE" at OIA SUNSET VILLAS is one of six Boutique Villas with Hotel Services, elegantly decorated. The villa is located in the north of Santorini Island in the traditional settlement of Oia (Ia) village. It is just 400 m. from the village, but so far enoug  …see more

from £235 / night

£2113 - £3452 / week

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from £235 / night

(1) Excellent 

20

Oia's nest - Oia house sleeps 4

Santorini / Oia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Suitable for children age 5+
Oia ,is the most famous village of Santorini. Practically a vertical village on the edge of caldera with amazing view. Except the main street linking with the capital village of Fira, are no streets but only narrow paths between the labyrinth of white houses most of th  …see more

from £140 / night

£853 - £1766 / week

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from £140 / night

10

Mystic Luxury Villa I, Caldera View & Jacuzzi - Oia villa sleeps 2

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • 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 £174 / night

£1218 - £2557 / week

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from £174 / night

5

Seafront house in Santorini - Oia house sleeps 5

Santorini / Oia

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Ask owner if suitable for children
  • Ask about pets
Amazing seafront house, located in Armeni picturesque small port, under the famous village of Oia with mesmerizing views to the volcano and the beautiful sunset. The house consists of 3 small bedrooms and one bigger one, it has traditional built in beds, small kitchen a  …see more

from £105 / night

£1740 / week

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from £105 / night

7

Aqua Dream Villa, indoor plunge pool - Oia villa sleeps 2

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • 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 £209 / night

£2192 - £2557 / week

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from £209 / night

(1) Very Good 

22

Absolut peace hideaway - Oia villa sleeps 6

Santorini / Oia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.6 km
  • Child friendly
  • Air conditioning
Peaceful and spacious this villa can offer perfect relaxation to a couple or a family of four or even six people. It has a beautiful garden and you can enjoy the serenity of the area. The upper level has the master bath and bedroom as well as a balcony to watch your mos  …see more

from £79 / night

£548 - £1044 / week

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from £79 / night

(6) Excellent 

37

House of the singing birds - Oia house sleeps 2

Santorini / Oia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Car not necessary
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 £81 / night

£567 - £688 / week

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from £81 / night

14

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

Santorini / Oia

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets
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 £200 / night

£1392 - £3227 / week

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from £200 / night

(3) Very Good 

23

The sunset windmill - Oia house sleeps 6

Santorini / Oia

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
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 £157 / night

£870 - £1087 / week

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from £157 / night

(11) Very Good 

29

Fava Eco Residences - Aeolos Suite - Oia apartment sleeps 3

Santorini / Oia

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
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 £122 / night

£767 - £1279 / week

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from £122 / night

10

Armeni Grand Family Suite GALATIA - Oia villa sleeps 5

Santorini / Oia

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
Armeni Luxury Villas is located in the most beautiful corner of Santorini, on the rock of the old town of Oia. It offers a unique breathtaking view of the volcanic caldera of Santorini and the deep blue of the Aegean Sea. Galatia Grand Family Suite, which is the great  …see more

from £253 / night

£1766 - £3987 / week

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from £253 / night

(3) Very Good 

5

Junior Architect's Cave House - Oia house sleeps 3

Santorini / Oia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
Carved into the Cliffside of Oia, you can experience the unique breathtaking view, along with the authentic elegance and luxury traditional style of the Architect’s Cave House. The Architect’s Cave House is consisting of two tranquil, stylish, traditional suites. Th  …see more

from £200 / night

£1400 - £1948 / week

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from £200 / night

(7) Excellent 

38

Sunny Winehouse - Oia house sleeps 2

Santorini / Oia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Pet friendly
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 £92 / night

£640 - £883 / week

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from £92 / night

(4) Excellent 

10

Santorini / Oia

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £112 / night

£831 - £1366 / week

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from £112 / night

(5) Excellent 

17

Evmenia Luxury Cave Villa - Oia villa sleeps 5

Santorini / Oia

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Air conditioning
Evmenia Luxury Cave Villa is a Self-catered home located in the heart of the traditional settlement of Oia. The villa offers a beautiful panoramic view of the magnificent Caldera and the unique crystal clear blue waters of the Aegean Sea. This private residence is an i  …see more

from £353 / night

£2466 / week

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from £353 / night

(14) Excellent 

31

Fava Eco Residences - Gaia Suite - Oia apartment sleeps 4

Santorini / Oia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
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 £131 / night

£822 - £1571 / week

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from £131 / night

(14) Excellent 

36

Fava Eco Residences - Helios Suite - Oia apartment sleeps 4

Santorini / Oia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
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 £122 / night

£767 - £1461 / week

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from £122 / night

8

Villa Erifili 28 sq. m. with a sea view! - Oia apartment sleeps 3

Santorini / Oia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Villa Erifili is the ideal place to stay for those wishing to relax in a beautiful and friendly ambience. Only 2000 meters from the world-renowned village of Oia and just a few steps from its beautiful black sandy beach. It is built according to the traditional archite  …see more

from £55 / night

£384 / week

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from £55 / night

(3) Very Good 

20

Pina Caldera Residence with Pool - Oia villa sleeps 2

Santorini / Oia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask owner if suitable for children
  • Pet friendly
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 £392 / night

£2740 / week

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from £392 / night

27

Blue Sky Cave House Oia Caldera - Oia cave house sleeps 4

Santorini / Oia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
Blue Sky cave house is located in the middle of the traditional village of OIA, only 5 minutes away from the main path, where cafes, restaurants and shops are placed. Also it takes 10 minutes walking distance to reach the main square where you can find the taxi and bus  …see more

from £87 / night

£1035 / week

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from £87 / night

10

Senior Architect's Cave House - Oia house sleeps 3

Santorini / Oia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
Carved into the Cliffside of Oia, you can experience the unique breathtaking view, along with the authentic elegance and luxury traditional style of the Architect’s Cave House. The Architect’s Cave House is consisting of two tranquil, stylish, traditional suites. Th  …see more

from £305 / night

£2131 - £2818 / week

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from £305 / night

(4) Very Good 

24

Absolut peace - Oia villa sleeps 4

Santorini / Oia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.5 km
  • Child friendly
  • Air conditioning
Quiet and spacious, laid out on two levels, our home is the ideal accommodation for a couple or a family of four. The upper level has the master bath and bedroom as well as a balcony to watch your most memorable sunrises from. The ground level consists of a living room  …see more

from £70 / night

£487 - £696 / week

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from £70 / night

Top Destination reviews

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
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
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
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
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

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