50 Best Oia Villas on Holiday Lettings - Vacation rentals

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174 Vacation rentals

(49) 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 $208 / night

$1381 - $2031 / week

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from $208 / night

(4) Excellent 

23

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 $208 / night

$1151 - $1439 / week

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from $208 / night

(5) Very Good 

32

Cave house rental in Oia

Santorini / Oia

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • 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 $173 / night

$1151 - $2416 / week

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from $173 / night

(12) 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 $185 / night

$1289 / week

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from $185 / night

12

Oia Vacation villa rental

Santorini / Oia

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $288 / night

$1956 - $3245 / week

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Responds fast!
avg. 3 hours 1 minutes

from $288 / 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 $185 / night

$1289 / week

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from $185 / night

21

Oia Vacation villa rental

Santorini / Oia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $288 / night

$1956 - $3245 / week

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Responds fast!
avg. 3 hours 1 minutes

from $288 / night

(6) 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 $466 / night

$3262 / week

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Responds fast!
avg. 1 hour 37 minutes

from $466 / night

(23) 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 $150 / night

$996 - $1933 / week

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from $150 / night

10

Vacation home in Oia

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. The ju …see more

from $403 / night

$2819 / week

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from $403 / 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 $668 / night

$4671 - $8778 / week

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from $668 / night

12

Vacation apartment rental

Santorini / Oia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $68 / night

$476 / week

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from $68 / night

(1) Very Good 

18

Oia Vacation villa rental

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 $317 / night

$2215 / week

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from $317 / night

8

Vacation villa in Oia

Santorini / Oia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 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 $323 / night

$2255 / week

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from $323 / night

(3) 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. The suite is luminous, with a cozy b …see more

from $311 / night

$2175 / week

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Responds fast!
avg. 2 hours 58 minutes

from $311 / night

(3) Excellent 

48

Vacation villa with shared pool in Oia

Santorini / Oia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $397 / night

$2505 - $5146 / week

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Responds fast!
avg. 3 hours 13 minutes

from $397 / night

(14) 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 $185 / night

$1289 / week

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from $185 / night

9

Vacation villa in Oia

Santorini / Oia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 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. Galini Superior Suite is a splendid villa offe …see more

from $317 / night

$2215 / week

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from $317 / night

10

Vacation villa in Oia

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 $334 / night

$2336 / week

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from $334 / night

(1) 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 $93 / night

$645 - $921 / week

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from $93 / night

(8) 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 $173 / night

$1208 / week

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from $173 / night

(3) Excellent 

41

Villa rental in Oia with shared pool

Santorini / Oia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $397 / night

$2505 - $5146 / week

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Responds fast!
avg. 3 hours 13 minutes

from $397 / 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 $93 / night

$645 - $921 / week

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from $93 / 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 $397 / night

$2779 - $6805 / week

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from $397 / night

10

Home rental in Oia

Santorini / Oia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets
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 $169 / night

$1310 - $1948 / week

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Responds fast!
avg. 3 hours 40 minutes

from $169 / night

(8) 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 $208 / night

$1450 / week

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from $208 / night

(1) Excellent 

46

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 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 $443 / night

$2795 - $5477 / week

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Responds fast!
avg. 3 hours 13 minutes

from $443 / night

(2) 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 $196 / night

$1370 / week

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from $196 / 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 $173 / night

$1208 / week

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from $173 / 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 $156 / night

$1036 - $1663 / week

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from $156 / night

15

Oia Vacation villa rental

Santorini / Oia

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 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 $248 / night

$1730 / week

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from $248 / night

(4) Excellent 

53

Oia Vacation villa rental

Santorini / Oia

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $627 / night

$3955 - $7434 / week

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Responds fast!
avg. 3 hours 13 minutes

from $627 / 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 $185 / night

$1289 / week

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from $185 / night

(1) 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 $105 / night

$731 - $1797 / week

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from $105 / night

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 $185 / night

$1289 / week

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from $185 / night

7

Vacation studio with shared pool in Oia

Santorini / Oia

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • 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 $81 / night

$564 / week

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from $81 / night

12

Oia Vacation villa rental

Santorini / Oia

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
Sea 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 si …see more

from $366 / night

$2557 / week

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from $366 / night

(5) Very Good 

20

Vacation villa in Oia

Santorini / Oia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about 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 charm …see more

from $1151 / night

$8054 / week

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from $1151 / night

(4) Very Good 

5

Oia Vacation home rental

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. The ju …see more

from $265 / night

$1853 / week

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from $265 / 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 $196 / night

$1370 / week

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from $196 / night