50 Best Oia Villas on Holiday Lettings - Vacation rentals

Close

Oia

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

171 Vacation rentals

Travelers going to Oia are booking June dates now. Secure your vacation rental today and have the perfect trip.

(46) 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 $112 / night

$636 - $1166 / week

Book View

from $112 / 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 $292 / night

$2041 / week

Book View

from $292 / night

7

Vacation villa rental

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Ask about children
White Pearl Villas in Oia, Santorini, carved in the volcanic rocks of Theran land with the mystical beauty of the caldera cliff, stretching before them, open their doors to take you on a magic trip. Built on the edge of the cliff through the centuries, restored with res  …see more

from $255 / night

$1781 - $3116 / week

Book View

from $255 / night

9

Villa rental in Oia

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about children
  • Car not necessary
  • Air conditioning
White Pearl Villas in Oia, Santorini, carved in the volcanic rocks of Theran land with the mystical beauty of the caldera cliff, stretching before them, open their doors to take you on a magic trip. Built on the edge of the cliff through the centuries, restored with res  …see more

from $297 / night

$2078 - $4007 / week

Book View

from $297 / 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 $85 / night

$594 - $848 / week

Book View

from $85 / 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 endles  …see more

from $138 / night

$917 - $1781 / week

Book View

from $138 / 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 studioThis is a unique accommodation proposal. Nested within the historical heart of Oia's village, the cave studio is built within the volcanic rock according to the traditional island's architecture which is adapted to Santorin  …see more

from $265 / night

$1855 / week

Book View

from $265 / night

(3) 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 su  …see more

from $244 / night

$1707 / week

Book View

from $244 / night

10

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
White Pearl Villas in Oia, Santorini, carved in the volcanic rocks of Theran land with the mystical beauty of the caldera cliff, stretching before them, open their doors to take you on a magic trip. Built on the edge of the cliff through the centuries, restored with res  …see more

from $255 / night

$1781 - $3116 / week

Book View

from $255 / night

(14) Excellent 

36

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 $170 / night

$1188 / week

Book View

from $170 / night

(12) Excellent 

10

Oia Vacation cave house rental

Santorini / Oia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Air conditioning
It is an appartment that can accomodate 2-3 persons.The appartment has private entrance and a private terrace, a fully equiped kitchen, a bathroom with shower, one double bed and one unfolded single bed, dining - sitting room with couch and an outdoor jacuzzi.It is a ca  …see more

from $105 / night

$735 - $2745 / week

Book View

from $105 / night

(20) 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 endles  …see more

from $138 / night

$917 - $1781 / week

Book View

from $138 / night

15

Oia Vacation cave house rental

Santorini / Oia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
It is a appartment that can accomodate 2-3 persons.The appartment has private entrance and a private terrace, a fully equiped kitchen, a bathroom with shower, one double bed and one unfolded single bed, dining room-sitting room with 2 couches and an indoor jacuzzi. It i  …see more

from $101 / night

$705 - $2745 / week

Book View

from $101 / night

(3) Very Good 

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 $191 / night

$1060 - $1325 / week

Book View

from $191 / night

(4) Very Good 

30

Cave house rental in Oia

Santorini / Oia

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights 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  …see more

from $265 / night

$1802 / week

Book View

from $265 / night

(11) Very Good 

29

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 $170 / night

$1188 / week

Book View

from $170 / night

(6) Excellent 

13

Vacation cave house rental

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
White Pearl Villas in Oia, Santorini, carved in the volcanic rocks of Theran land with the mystical beauty of the caldera cliff, stretching before them, open their doors to take you on a magic trip. Built on the edge of the cliff through the centuries, restored with res  …see more

from $293 / night

$2048 - $3383 / week

Book View

from $293 / 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 a  …see more

from $255 / night

$1781 / week

Book View

from $255 / 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 $85 / night

$594 - $848 / week

Book View

from $85 / night

19

Vacation home in Oia

Santorini / Oia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Nestled on the cliffs of the worldwide famous village of Oia, "Kalidoscope cave villas" welcome you to the beautiful island of Santorini. Gazing the deep blue, Kalidoscope is a complex of three traditional cave houses ideal for all visitors’ who wish to  …see more

from $276 / night

$1929 / week

Book View

from $276 / night

(14) Excellent 

31

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 $170 / night

$1188 / week

Book View

from $170 / night

(3) Excellent 

40

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 &ld  …see more

from $366 / night

$2308 - $3940 / week

Book View

from $366 / 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 i  …see more

from $578 / night

$3643 - $5299 / week

Book View

from $578 / night

(1) Excellent 

38

Villa rental in Oia with shared pool

Santorini / Oia

3 6 Min stay varies

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

from $409 / night

$2575 - $4207 / week

Book View

from $409 / night

(2) Excellent 

22

Oia Vacation villa rental

Santorini / Oia

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 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 infini  …see more

from $366 / night

$2560 - $7011 / week

Book View

from $366 / night

(2) 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  …see more

from $287 / night

$2004 / week

Book View

from $287 / night

(2) Excellent 

43

Vacation villa with shared pool in Oia

Santorini / Oia

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa "EMERALD" 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  …see more

from $409 / night

$2575 - $4207 / week

Book View

from $409 / 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 $292 / night

$2041 / week

Book View

from $292 / 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 $308 / night

$2152 / week

Book View

from $308 / night

(5) Excellent 

33

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 $191 / night

$1336 / week

Book View

from $191 / night

(8) Very Good 

29

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 $159 / night

$1113 / week

Book View

from $159 / night

17

Vacation villa in Oia

Santorini / Oia

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Ask about children
White Pearl Villas in Oia, Santorini, carved in the volcanic rocks of Theran land with the mystical beauty of the caldera cliff, stretching before them, open their doors to take you on a magic trip. Built on the edge of the cliff through the centuries, restored with res  …see more

from $446 / night

$3116 - $6677 / week

Book View

from $446 / night

(4) Excellent 

14

Vacation cave house accommodation

Santorini / Oia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Car not necessary
White Pearl Villas in Oia, Santorini, carved in the volcanic rocks of Theran land with the mystical beauty of the caldera cliff, stretching before them, open their doors to take you on a magic trip. Built on the edge of the cliff through the centuries, restored with res  …see more

from $340 / night

$2375 - $5342 / week

Book View

from $340 / 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 $159 / night

$1202 - $1573 / week

Book View

from $159 / 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 $96 / night

$668 - $1272 / week

Book View

from $96 / night

(6) Excellent 

27

Santorini / Oia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Ask about children

 …see more

from $382 / night

$2894 / week

Book View

from $382 / night

7

Vacation villa in Oia

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning
White Pearl Villas in Oia, Santorini, carved in the volcanic rocks of Theran land with the mystical beauty of the caldera cliff, stretching before them, open their doors to take you on a magic trip. Built on the edge of the cliff through the centuries, restored with res  …see more

from $255 / night

$1781 - $3116 / week

Book View

from $255 / night

(6) Very Good 

28

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 $181 / night

$1262 / week

Book View

from $181 / 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 &ldq  …see more

from $366 / night

$2308 - $3940 / week

Book View

from $366 / night

8

Vacation apartment rental

Santorini / Oia

1 3 1 night min

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

from $112 / night

$779 / week

Book View

from $112 / night