50 Best Oia Villas on Holiday Lettings - Vacation rentals

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854 Vacation rentals

(4) Excellent 

53

Oia Vacation villa rental

Santorini / Oia

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Swinging Sunset 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 enough away from “civilization” to be peaceful and the same time quiet. Ammoudi bay is just in walking di …see more

from $759 / night

$4,786 - $7,893 / week

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Responds fast!
avg. 3 hours 45 minutes

from $759 / night

(26) Excellent 

10

Oia Vacation cave house rental

Santorini / Oia

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about 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 endless blu …see more

from $279 / night

$1,947 / week

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from $279 / night

(52) Very Good 

11

Oia Vacation studio rental

Santorini / Oia

Studio 3 3 nights min

  • Studio
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • 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 $226 / night

$1,582 - $2,393 / week

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from $226 / night

18

Vacation apartment rental

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 $70 / night

$487 / week

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from $70 / night

9

Oia Vacation cave house rental

Santorini / Oia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 mi
  • Air conditioning
A romantic retreat dedicated to revitalizing the mind. Located on the lower levels of Liakada Oia Suites, these luxurious suites feature an open-plan styled bedroom with a queen-size bed, a spacious living room area, a fully equipped kitchenette and a commodious bathroo …see more

from $255 / night

$1,739 - $3,975 / week

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from $255 / night

(15) Excellent 

32

Oia Vacation apartment rental

Santorini / Oia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • 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 $163 / night

$1,022 - $2,787 / week

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from $163 / night

8

Vacation villa in Oia

Santorini / Oia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
Located at the Caldera cliff in an isolated spot at Oia town, it is a dreamy cave-style Suite handcrafted from local material, boasts a secluded terrace that peers out onto the deep blue Aegean sea and the volcano. It consists of one spacious bedroom with king size bed …see more

from $290 / night

$2,028 / week

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from $290 / night

(3) Excellent 

60

Vacation villa with shared pool in Oia

Santorini / Oia

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Villa "PEARL" at OIA SUNSET VILLAS is one of six boutique villas, 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 enough away from “civilization” …see more

from $481 / night

$3,034 - $5,184 / week

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avg. 3 hours 45 minutes

from $481 / night

(7) Excellent 

18

Vacation villa in Oia

Santorini / Oia

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 4 mi
  • Car not necessary
  • 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 $470 / night

$3,285 / week

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avg. 1 hour 57 minutes

from $470 / night

(4) Very Good 

24

Oia Vacation villa rental

Santorini / Oia

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 0.5 mi
  • 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 $105 / night

$730 - $1,182 / week

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Responds fast!
avg. 3 hours 20 minutes

from $105 / night

(1) Excellent 

42

Vacation villa in Oia

Santorini / Oia

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Villa Altana is among the newest additions on the Fava Eco collection of houses. The private property comprises of a main living and sitting area accompanied with 3 separate bedrooms with double queen beds. It has one large and one small kitchen as well as two separate …see more

from $186 / night

$1,168 - $6,814 / week

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from $186 / night

(2) Very Good 

22

Vacation villa in Oia

Santorini / Oia

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.6 mi
  • 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 $116 / night

$812 - $1,426 / week

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avg. 3 hours 20 minutes

from $116 / night

9

Vacation studio in Oia

Santorini / Oia

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 1 mi
  • Car not necessary
  • Air conditioning
Traditional exclusive cave studio This 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's unique …see more

from $290 / night

$2,028 / week

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Responds fast!
avg. 3 hours 31 minutes

from $290 / night

(1) Excellent 

20

Vacation villa in Oia

Santorini / Oia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
Located in one of the most characteristic spots in the center of Oia, offering infinity views to the deep blue waters of Caldera with a beautifully decorated terrace, where you can have your breakfast and relax on the sunbeds. It consists of one master bedroom with en s …see more

from $290 / night

$2,028 / week

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from $290 / night

(5) Very Good 

32

Cave house rental in Oia

Santorini / Oia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Child friendly
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 $163 / night

$927 - $4,543 / week

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from $163 / night

(14) Excellent 

34

Apartment rental in Oia

Santorini / Oia

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • 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 $174 / night

$1,095 - $2,751 / week

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from $174 / night

(6) Excellent 

22

Oia Vacation villa rental

Santorini / Oia

4 7 1 night min

  • 4 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets
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 $400 / night

$2,799 - $6,854 / week

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Responds fast!
avg. 3 hours 58 minutes

from $400 / night

(4) Very Good 

30

Vacation apartment in Oia

Santorini / Oia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • 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 $174 / night

$1,095 - $3,254 / week

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from $174 / night

(14) Excellent 

37

Oia Vacation apartment rental

Santorini / Oia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • 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 $163 / night

$1,022 - $2,787 / week

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from $163 / night

(7) Very Good 

30

Vacation apartment in Oia

Santorini / Oia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • 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 $151 / night

$949 - $1,963 / week

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from $151 / night

(4) Excellent 

17

Oia Vacation cave house rental

Santorini / Oia

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • 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. Lava Cave used to be a sailor's d …see more

from $290 / night

$2,028 / week

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from $290 / night

(1) Excellent 

45

Villa rental in Oia with shared pool

Santorini / Oia

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa "TURQUOISE" at OIA SUNSET VILLAS is one of six Boutique Villas 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 enough away from “civilizat …see more

from $533 / night

$3,358 - $5,516 / week

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Responds fast!
avg. 3 hours 45 minutes

from $533 / night

(5) Excellent 

38

Vacation apartment in Oia

Santorini / Oia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • 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 $186 / night

$1,168 - $3,254 / week

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from $186 / night

21

Vacation home in Oia

Santorini / Oia

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 2 mi
  • Air conditioning
Naftilos Boutique Houses welcomes you to the island of Santorini, the most beautiful in the world. Isalos Cave Suite is located in a picturesque and traditional village of Santorini, the housing complex is dating from 1928 and has been renovated recently in 2016. It is …see more

from $163 / night

$1,101 - $1,385 / week

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Responds fast!
avg. 3 hours 18 minutes

from $163 / night

(6) Very Good 

57

Vacation home in Oia

Santorini / Oia

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • 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 $232 / night

$1,391 - $2,086 / week

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from $232 / night

(9) Very Good 

32

Vacation apartment in Oia

Santorini / Oia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • 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 $151 / night

$949 - $1,963 / week

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from $151 / night

(9) Very Good 

37

Oia Vacation villa rental

Santorini / Oia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • 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 $186 / night

$1,168 - $4,413 / week

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from $186 / night

4

Vacation villa in Oia

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
As soon as 2000 meters from the world famous village of Oia. Includes: Bedroom with large king size bed, dining area, bathroom with shower, and wonderful sea views This villa can accommodate 2 people …see more

from $70 / night

$488 / week

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from $70 / night

(1) Excellent 

16

Vacation cave house in Oia

Santorini / Oia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden
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 kingsizebed is perfect for couples in romantic holidays. The Space …see more

from $325 / night

$2,272 / week

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from $325 / night

(1) Excellent 

28

Villa rental in Oia

Santorini / Oia

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
Perched on the top row of the Caldera, only a few steps away from the main street of Oia, this home offers over 200 degree views of the spectacular Aegean. Villa Oia 1880 was built in 1880 as the home of the local doctor in Oia. Totally refurbished recently, the home o …see more

from $676 / night

$4,732 / week

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from $676 / night

(3) Excellent 

51

Villa rental in Oia with shared pool

Santorini / Oia

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa "TOPAZ" of OIA SUNSET VILLAS is one of six boutique villas, 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 enough away from “civilization …see more

from $481 / night

$3,034 - $5,184 / week

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Responds fast!
avg. 3 hours 45 minutes

from $481 / night

(1) Excellent 

24

Vacation villa rental

Santorini / Oia

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Nearest beach 1 mi
  • Child friendly
  • Car not necessary
Villa Potamos is a luxurious completely renovated traditional private house of 65 m2 net area that comprises of a large main living and sitting area with 4 single beds, accompanied with a separate bedroom with a double queen bed on the upper floor. It also has a fully e …see more

from $174 / night

$1,095 - $4,260 / week

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from $174 / night

10

Vacation cave house in Oia

Santorini / Oia

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 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 Space …see more

from $145 / night

$1,014 / week

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from $145 / night

(2) Very Good 

19

Vacation villa in Oia

Santorini / Oia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.5 mi
  • 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 $105 / night

$731 - $1,184 / week

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Responds fast!
avg. 3 hours 20 minutes

from $105 / night

(2) Excellent 

20

Vacation home in Oia

Santorini / Oia

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • 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 $186 / night

$1,298 / week

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from $186 / night

16

Vacation home in Oia

Santorini / Oia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Air conditioning
Naftilos Boutique Houses welcomes you to the island of Santorini, the most beautiful in Greece!! Sofrano apartment is dating from 1928 and has been renovated recently in 2015. The apartment is equipped with all modern facilities and it has great sea-view offering its g …see more

from $163 / night

$914 / week

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Responds fast!
avg. 3 hours 18 minutes

from $163 / night

8

Vacation cave house in Oia

Santorini / Oia

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 4 mi
  • Child friendly
  • Air conditioning
The double space Deluxe Suite with outdoor hot tub is distinguished by the ample space and its graceful ambience. It offers a stylishly designed master bedroom with a comfortable queen-size bed and an elegantly adorned bathroom with a rejuvenating shower. This chic Sui …see more

from $510 / night

$3,477 - $4,774 / week

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from $510 / night

4

Studio rental in Oia with shared pool

Santorini / Oia

Studio 3 1 night min

  • Studio
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
In a quiet place in Oia, with the magnificent view of the Aegean sea and the amazing sunset of Santorini island you will find Villa Pezoula. The hotel is build in such a location that has a magnificent panoramic view to the world famous sunset of Oia, Santorini. You ca …see more

from $117 / night

$813 / week

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from $117 / night

7

Oia Vacation studio rental

Santorini / Oia

Studio 3 1 night min

  • Studio
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
The rooms are equipped with air conditioning, TV, kitchenette and refrigerator. Situated on a beachfront location in Oia, Vrachia Studios offers traditionally decorated rooms with spacious balconies and sea views. It features a sun terrace and free Wi-Fi throughout. It …see more

from $83 / night

$576 / week

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from $83 / night

12

Vacation villa in Oia

Santorini / Oia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Perched in the cliffs of Oia village, Ocean Blue Cave boasts panoramic views of the Caldera, volcano and the Aegean Sea from its furnished terrace. It offers villas with cave-style, minimalist design and free WiFi. Fitted with built-in beds and sofas, the villa consist …see more

from $406 / night

$2,839 / week

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from $406 / night