50 Best Oia Villas on Holiday Lettings - Vacation rentals

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862 Vacation rentals

(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 $240 / night

$1,677 - $2,536 / week

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from $240 / 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 $565 / night

$3,559 - $5,846 / week

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Responds fast!
avg. 3 hours 38 minutes

from $565 / 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 $295 / night

$2,064 / week

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from $295 / 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 $498 / night

$3,482 / week

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Responds fast!
avg. 1 hour 57 minutes

from $498 / night

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

$1,843 - $4,213 / week

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from $271 / 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 $74 / night

$516 / week

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from $74 / 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 $307 / night

$2,150 / week

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Responds fast!
avg. 3 hours 31 minutes

from $307 / 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 $805 / night

$5,072 - $8,365 / week

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Responds fast!
avg. 3 hours 38 minutes

from $805 / 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

$735 - $3,577 / week

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from $117 / 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 $424 / night

$2,966 - $7,264 / week

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from $424 / 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 $172 / night

$1,167 - $1,468 / week

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Responds fast!
avg. 3 hours 18 minutes

from $172 / 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 $714 / night

$4,998 / week

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from $714 / 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 $99 / night

$688 / week

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from $99 / night

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 $133 / night

$835 - $7,221 / week

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from $133 / 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 $111 / night

$697 - $2,954 / week

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from $111 / 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 $172 / night

$1,167 - $1,468 / week

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Responds fast!
avg. 3 hours 18 minutes

from $172 / 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

$735 - $2,916 / week

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from $117 / 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 $307 / night

$2,150 / week

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from $307 / 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 $172 / night

$983 - $4,814 / week

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from $172 / night

(5) Excellent 

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 $246 / night

$1,474 - $2,211 / week

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from $246 / 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 $111 / night

$774 - $1,253 / week

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from $111 / 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 $133 / night

$835 - $4,677 / week

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from $133 / 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 $197 / night

$1,376 - $1,892 / week

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from $197 / 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

$627 - $2,081 / week

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from $100 / 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

$697 - $2,954 / week

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from $111 / 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

$735 - $3,449 / week

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from $117 / 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 $510 / night

$3,215 - $5,494 / week

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Responds fast!
avg. 3 hours 38 minutes

from $510 / night

(2) Very Good 

19

Vacation villa in Oia

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 w …see more

from $111 / night

$774 - $1,253 / week

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from $111 / 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 $510 / night

$3,215 - $5,494 / week

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Responds fast!
avg. 3 hours 38 minutes

from $510 / 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

$627 - $2,081 / week

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from $100 / 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 $307 / night

$2,150 / week

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from $307 / night

(9) Excellent 

27

Villa rental in Oia

Santorini / Oia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Ask about children
Villa Domus Solis has two bedrooms each with own bathroom, modern and fully equipped and the living room can accommodate a fifth person. Vaulted ceilings and linen fabrics, sofas, cushions and elegant recessed furniture handmade make higher level of accommodation. At Vi …see more

from $479 / night

$3,353 / week

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Responds fast!
avg. 3 hours 18 minutes

from $479 / 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 $123 / night

$860 / week

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from $123 / night

10

Vacation villa in Oia

Santorini / Oia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
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 $357 / night

$2,493 / week

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from $357 / night

8

Oia Vacation villa rental

Santorini / Oia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Passion Blue Villas is one of the few captain’s houses which have survived through time in Oia of the 19th century. The captain's houses are architectural achievements and decorations of a different era. High-ceilinged, built exclusively with island materials (red and b …see more

from $541 / night

$3,783 / week

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from $541 / 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 $123 / night

$860 - $1,511 / week

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from $123 / night

9

Vacation villa in Oia

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
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. Galini Superior Suite is a splendid villa offe …see more

from $338 / night

$2,364 / week

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from $338 / night

14

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 $295 / night

$2,064 / week

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from $295 / night

(1) Excellent 

50

Oia Vacation home rental

Santorini / Oia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 1 mi
  • Air conditioning
Santorini Perfect Villas is a private company owning and managing a collection of self-catering properties based on Santorini. We are looking forward to welcoming you in our beautiful island! Marianna & Gregory Each of our hand-picked Villa and House is selected fol …see more

from $357 / night

$2,493 - $4,127 / week

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from $357 / 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 $737 / night

$5,158 / week

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from $737 / night