50 Best Oia Villas on Holiday Lettings - Vacation rentals

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165 Vacation rentals

(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 $113 / night

$641 - $1175 / week

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from $113 / 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 $294 / night

$2056 / week

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from $294 / 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 $86 / night

$598 - $2766 / week

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from $86 / night

(20) Excellent 

10

Oia Vacation cave house rental

Santorini / Oia

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 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 $134 / night

$855 - $1303 / week

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from $134 / 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 $86 / night

$598 - $855 / week

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from $86 / 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 $193 / night

$1068 - $1335 / week

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from $193 / night

(11) 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 $86 / night

$598 - $2766 / week

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from $86 / 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 $267 / night

$1869 / week

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from $267 / 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 has 2 bed  …see more

from $267 / night

$1816 / week

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from $267 / 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 $68 / night

$471 / week

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from $68 / night

(5) Excellent 

17

Vacation villa in Oia

Santorini / Oia

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • 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 $433 / night

$3028 / week

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from $433 / 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 $342 / night

$2392 - $5382 / week

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from $342 / 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 $113 / night

$785 / week

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from $113 / 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 $257 / night

$1794 / week

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from $257 / night

(12) 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 $214 / night

$1346 - $1570 / week

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from $214 / night

(3) Excellent 

40

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 “civilizati  …see more

from $369 / night

$2325 - $3969 / week

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from $369 / 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 $214 / night

$1346 - $1794 / week

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from $214 / 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 $86 / night

$598 - $855 / week

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from $86 / night

(2) Very Good 

29

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 $235 / night

$1480 - $1929 / week

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from $235 / night

(1) Excellent 

27

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 $430 / night

$3008 / week

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from $430 / 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 $97 / night

$673 - $1282 / week

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from $97 / 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 $235 / night

$1480 - $1929 / week

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from $235 / night

(1) Excellent 

38

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 $412 / night

$2594 - $4239 / week

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from $412 / 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 $193 / night

$1211 - $1436 / week

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from $193 / 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 $299 / night

$2093 - $4037 / week

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from $299 / 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 $193 / night

$1211 - $1436 / week

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from $193 / 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 $257 / night

$1794 - $3140 / week

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from $257 / 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 $257 / night

$1794 - $3140 / week

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from $257 / 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 cozy  …see more

from $289 / night

$2019 / week

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from $289 / 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 walkin  …see more

from $582 / night

$3671 - $5338 / week

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from $582 / 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 $310 / night

$2168 / week

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from $310 / 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 $235 / night

$1480 - $1929 / week

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from $235 / night

5

Santorini / Oia

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $161 / night

$1122 / week

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from $161 / 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. Th  …see more

from $374 / night

$2617 / week

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from $374 / night

7

Vacation villa rental

Santorini / Oia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • 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. Glafki Ambassador Villa is a gorgeous villa of  …see more

from $332 / night

$2467 - $2766 / week

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from $332 / 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 $295 / night

$2063 - $3409 / week

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from $295 / night

(2) Excellent 

43

Vacation villa with shared pool in Oia

Santorini / Oia

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • 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 “civiliz  …see more

from $412 / night

$2594 - $4239 / week

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from $412 / night

(15) Excellent 

40

Vacation villa with swimming pool in Oia

Santorini / Oia

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Live your dream wedding at the Diamond Rock Venue, with panoramic views of the mysterious caldera, the stunning volcano and the magnificent blue of the Aegean Sea, feeling the vibrant energy and distinctive character of Santorini. Diamond Rock Venue can accommodate up  …see more

from $2456 / night

$17192 / week

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from $2456 / night

10

Vacation villa in Oia

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Ask about children
  • Car not necessary
The White Pearl Villas are scattered in Oia, are completely autonomous and private, and will undoubtedly fascinate you with their impeccable style, comfort, decoration and breathtaking view of Caldera and the volcano. Each property has a different layout and distinctiv  …see more

from $257 / night

$1794 / week

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from $257 / night

9

Villa rental in Oia

Santorini / Oia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Ask about children
  • Car not necessary
The White Pearl Villas are scattered in Oia, are completely autonomous and private, and will undoubtedly fascinate you with their impeccable style, comfort, decoration and breathtaking view of Caldera and the volcano. These private villas will be your home away from ho  …see more

from $214 / night

$1495 / week

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from $214 / night