50 Best Oia Villas on Holiday Lettings - Vacation rentals

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858 Vacation rentals

9

Oia Vacation cave house rental

Santorini / Oia

1 2 Min stay varies

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

from $271 / night

$1,846 - $4,220 / week

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from $271 / night

(13) 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 $117 / night

$736 - $2,652 / week

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from $117 / 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 $242 / night

$1,692 - $2,559 / week

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from $242 / night

(3) Very Good 

15

Vacation villa in Oia

Santorini / Oia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
Villa Ambrosia is located in a quiet area of the cliffside village of Oia which is at the tip of the island of Santorini. The house is in the style of the traditional Oia village cave homes but with all the modern conveniences. It faces towards the sea, volcano and the …see more

from $744 / night

$5,204 / week

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from $744 / 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 $100 / night

$628 - $1,895 / week

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from $100 / 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 $308 / night

$2,153 / week

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Responds fast!
avg. 3 hours 31 minutes

from $308 / night

(5) Excellent 

38

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 $248 / night

$1,487 - $2,230 / week

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from $248 / night

12

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 $78 / night

$547 / week

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from $78 / night

(14) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $112 / night

$703 - $2,706 / week

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from $112 / night

(7) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from $100 / night

$628 - $1,895 / week

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from $100 / night

(4) Very Good 

24

Oia Vacation villa rental

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 …see more

from $112 / night

$694 - $1,264 / week

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from $112 / night

(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 $812 / night

$5,117 - $8,439 / week

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Responds fast!
avg. 3 hours 34 minutes

from $812 / 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 $155 / night

$1,084 / week

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from $155 / 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 $111 / night

$698 - $2,687 / week

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from $111 / 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 $112 / night

$694 - $1,264 / week

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from $112 / 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 $117 / night

$736 - $3,582 / week

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from $117 / 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 $511 / night

$3,221 - $5,503 / week

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Responds fast!
avg. 3 hours 34 minutes

from $511 / 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 $515 / night

$3,244 - $5,542 / week

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Responds fast!
avg. 3 hours 34 minutes

from $515 / 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 $570 / night

$3,591 - $5,898 / week

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Responds fast!
avg. 3 hours 34 minutes

from $570 / night

(1) Excellent 

31

Oia Vacation villa rental

Santorini / Oia

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly
In a serene environment that offers privacy and refined architecture together with a unique, exclusive view of the most famous sunset in Greece, this newly built villa complex, built right on the edge of Oia, offers the best of both worlds: designed in traditional Cycla …see more

from $304 / night

$2,127 / week

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Responds fast!
avg. 2 hours 41 minutes

from $304 / 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 $347 / night

$2,429 / week

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from $347 / night

(5) 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 $425 / night

$2,971 - $7,276 / week

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from $425 / night

(25) 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 $296 / night

$2,067 / week

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from $296 / night

(9) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from $134 / night

$843 - $4,718 / week

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from $134 / night

(2) Very Good 

22

Vacation villa in Oia

Santorini / Oia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $124 / night

$781 - $1,524 / week

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from $124 / night

11

Oia Vacation apartment rental

Santorini / Oia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
Sand Luxury Villa in Santorini ,was constructed in 2015 with the principal objective to offer visitors the quality time they deserve for perfect holidays. It is located in the quiet area of Exo Gialos, Karterados, near the organized beach of Monolithos, on the eastern s …see more

from $81 / night

$564 / week

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from $81 / night

6

Vacation apartment with shared pool in Oia

Santorini / Oia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
The rooms are equipped with air conditioning, TV, kitchenette and refrigerator. Our hotel enjoys a privileged location by the sea. It is 4 km from the center of Oia, while just 600 meters from here you will find many taverns which serve local specialties. Very close …see more

from $109 / night

$764 / week

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from $109 / night

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 $308 / night

$2,153 / week

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from $308 / 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 $117 / night

$736 - $3,135 / week

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from $117 / night

30

Oia Vacation home accommodation

Santorini / Oia

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Daphne is a unique property located on the highest point of Oia village in Perivolas area, in a very convenient position, since it is only 500 meters from Oia center and just outside the property there is a parking area, the bus stop, markets and restaurants. Daphn …see more

from $775 / night

$5,429 - $10,010 / week

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from $775 / 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 $502 / night

$3,513 / week

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Responds fast!
avg. 1 hour 42 minutes

from $502 / night

(4) Excellent 

17

Oia Vacation cave house rental

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. Lava Cave used to be a sailor's d …see more

from $310 / night

$2,169 / week

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Responds fast!
avg. 2 hours 52 minutes

from $310 / night

(7) Very Good 

32

Oia Vacation apartment rental

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 $117 / night

$736 - $3,135 / week

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from $117 / night

19

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. Verina Cave Suite is located in a picturesque and traditional village of Santorini but fully equipped with all the amenities of a 5-star hotel. The housing complex is dati …see more

from $174 / night

$1,177 - $1,481 / week

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Responds fast!
avg. 3 hours 18 minutes

from $174 / night

27

Oia Vacation villa rental

Santorini / Oia

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Car not necessary
In the cosmopolitan heart of the island, in the village Oia, just a few steps away from the caldera views and the breathtaking sunset, there is a comfortable place to relax and spend time with your family and friends or have your wedding ceremony and party on the mansio …see more

from $434 / night

$3,036 / week

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Responds fast!
avg. 2 hours 56 minutes

from $434 / 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 $199 / night

$1,388 - $1,908 / week

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from $199 / 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 $174 / night

$977 / week

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Responds fast!
avg. 3 hours 18 minutes

from $174 / 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 $542 / night

$3,691 - $5,068 / week

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from $542 / night

16

Vacation home in Oia

Santorini / Oia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
Gazing the deep blue, Kalidoscope is a complex of three traditional, fully renovated cave houses ideal for all visitors’ who wish to experience a traditional, modern home accommodation in Santorini. The traditional style houses offer a unique view, a comfortable and war …see more

from $296 / night

$2,067 / week

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from $296 / 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 $124 / night

$868 / week

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from $124 / night