50 Best Wailea Condos on Holiday Lettings - Vacation rentals

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135 Vacation rentals

(18) Excellent 

25

Vacation apartment in Wailea

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Car not necessary
Here's is your chance to experience this gorgeous condo at the Palms at Wailea. Newly renovated fully air conditioned, Charcoal grey bamboo floors, Whotel Pillow top Cal king mattress including the WHotel feather bed that makes you feel like your floating. There is als …see more

from $125 / night

$1391 - $1900 / week

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from $125 / night

(16) Excellent 

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting …see more

from $540 / night

$3780 - $6475 / week

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from $540 / night

(1) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting …see more

from $446 / night

$3122 - $5425 / week

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from $446 / night

(4) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
A note from the owner: Welcome to our piece of paradise. We love time at our Makena Surf unit. Uniquely located on the second floor of B building, we see the spectacular beach and ocean view up-close-and-personal from the privacy of the second floor. Sitting on the lana …see more

from $612 / night

$4284 - $7175 / week

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from $612 / night

25

Wailea Vacation condo rental

Maui / Wailea

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
LOCATION LOCATION LOCATION! This was the reason my investment dream stopped here,.... I had found Island Surf! You can not help to fall in love with the southern part of Kihei. Park your rental car and walk to EVERYTHING. The convenient amenities of this condo are very …see more

from $119 / night

$833 / week

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from $119 / night

(7) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
A Note from The Owners: Our dream-come-true was to have a unit directly overlooking the beach at Makena. We can literally talk to each other from the lanai to the beach! We did a remodel which, among other features, allows us to push all the glass doors back into the wa …see more

from $499 / night

$3493 - $7175 / week

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from $499 / night

(7) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting …see more

from $519 / night

$3633 - $7175 / week

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from $519 / night

(1) Excellent 

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting …see more

from $776 / night

$5425 - $10493 / week

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from $776 / night

(7) Very Good 

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
A Note from the Owner: Of all the units in Makena Surf, the original developer of the resort kept this one for himself! This rare corner unit provides panoramic ocean and beach views and overlooks the historic landmark Heiau garden. The one of a kind location and large …see more

from $612 / night

$4284 - $7175 / week

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from $612 / night

(4) Excellent 

24

Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Newly remodeled, Two bedroom / Two bathroom, second floor condominium right on the Beach! It is perfect for two couples or a family of four. You are literally steps from the beach! This condominium is at the front of the building closest to the ocean making for spectacu …see more

from $690 / night

$4515 - $5845 / week

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from $690 / night

20

Vacation apartment with shared pool in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! This beautiful two bedroom, two bath condominium overlooks the Wailea Blue Course. Enjoy the golf and ocean views while sitting on the lanai for sunset or morning coffee. The living area featur …see more

from $305 / night

$1890 - $2765 / week

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from $305 / night

(2) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
A note from the owner: "Our unit overlooks a beautiful cove, where in the late afternoon, we can see the turtles swimming on the surface of the ocean and popping their heads out of the water. We especially like to see how the color of the ocean changes during the day as …see more

from $459 / night

$3213 - $6475 / week

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from $459 / night

(16) Excellent 

16

Apartment rental in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
A note from the owner: Welcome to Wailea Elua Village #307, our newly remodeled ground floor condo and our piece of paradise. With outstanding views, beach access through beautifully sculpted gardens, and Hawaiian-home class, it has everything you need for your Maui vac …see more

from $383 / night

$2681 - $4816 / week

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from $383 / night

(1) Excellent 

24

Vacation villa with golf nearby in Wailea

Maui / Wailea

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
TAKE ADVANTAGE OF THE BEST DEAL IN HOOLEI. SPECIAL CANCELLATION RATE IS FOR MINIMUM 7 NIGHT BOOKING DURING 5/7-17/2016. Check availability and BOOK before its gone! Newly built state-of-the-art luxury townhome. Beautiful three bedroom, three and one-half baths, 3363 …see more

from $725 / night

$5075 / week

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from $725 / night

(37) Excellent 

20

Wailea Vacation apartment accommodation

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Our Prime Oceanfront 2 bedroom, 2 bathroom Makena Surf F304 condo in the Wailea area provides Unsurpassed Ocean Views from Molikini to West Maui Mountains. A major designer coordinated remodel and upgrade has been completed resulting in a home away from home with only h …see more

from $495 / night

$4375 - $6965 / week

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from $495 / night

(8) Excellent 

17

Condo rental in Wailea with shared pool, golf nearby

Maui / Wailea

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
50A is the perfect blend of luxury and value. Less than a 5 minute walk from Ekahi's beach front pool (or 1 minute to two other pools) and outfitted to offer the comforts of home, this condo is perfect for your Hawaii vacation. Ekahi 50A is a spacious 1BR/ 2 bath condo …see more

from $220 / night

$1540 / week

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from $220 / night

16

Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
A note from the owner. Welcome to our Maui ohana. Our unit is special because of the extra space and privacy, including the cool, shady side lanai we call our grotto - the perfect place to curl up with a good book, and a lovely respite from the afternoon heat! From our …see more

from $540 / night

$3780 - $6475 / week

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from $540 / night

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping. Beautiful Ulua Beach fr …see more

from $440 / night

$3080 - $5951 / week

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from $440 / night

(3) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting …see more

from $750 / night

$5250 - $7175 / week

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from $750 / night

25

Vacation apartment with shared pool in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! Enjoy views of Kahoolawe, Molokini and Lana’i all from this condo’s wonderful location. Vaulted ceilings, fresh paint, and brand new furnishings throughout entire condo. Comfortable living room …see more

from $335 / night

$2205 - $2765 / week

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from $335 / night

10

Wailea Vacation condo rental

Maui / Wailea

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a great 2 bedroom and 2 full bath unit for 'the island explorer' and guests who come to enjoy the outdoors of Hawaii with all its beaches, waterfalls, tropical forests or pineapple fields and Luaus . This condo has everything you might need on your vacation< (ye …see more

from $130 / night

$910 / week

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from $130 / night

(12) Excellent 

16

Apartment rental in Wailea

Maui / Wailea

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
A note from the owner: Wailea Elua Village #1305 boasts 3 bedrooms (king bed in the master, queen bed in the 2nd bedroom and 2 twin beds in the 3rd bedroom) and a prime oceanfront ground floor location just steps from the white sands of Elua Beach. The master bedroom lo …see more

from $1166 / night

$8162 - $12593 / week

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from $1166 / night

(17) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Notes from the Owner: Wailea Elua Village #801 is located in the center of the Elua Village just across from the small pool and Jacuzzi area and just steps to the paddle court. Enjoy ocean views as well as secluded garden views from this quiet ground floor, two bedroom, …see more

from $383 / night

$2681 - $4816 / week

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from $383 / night

(2) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting …see more

from $473 / night

$3311 - $6125 / week

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from $473 / night

(9) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
About this condo: Wailea Elua Village #105 is a ground floor, two bedroom-two bath, ocean view condo with a large lanai complete with a sun shade screen. It has a king bed in the master bedroom, twins in the guest bedroom and a sofa sleeper for additional guests. This u …see more

from $383 / night

$2681 - $4816 / week

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from $383 / night

(4) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
About this condo: Wailea Elua Village #1702 is a newly remodeled, second floor, two bedroom- two bath condo designed with a living room, dining room and kitchen that openly flow together. New cabinets, granite counter tops, new living room carpet, two lanais and new app …see more

from $599 / night

$4193 - $8400 / week

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from $599 / night

(1) Excellent 

25

Vacation apartment with shared pool in Wailea

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Our condo in Ekolu Village also has beautiful sweeping views of the ocean and the islands. We are located on the Blue Golf Course and just a short walk to the shops and restaurants in Wailea. Just beyond the shops and restaurants is a beautiful walkway along the beach a …see more

from $175 / night

$1225 - $1820 / week

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from $175 / night

(7) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
A Note From the Owner: You will love the extra space in this remodeled supersized two-bedroom, two-bath Elua condo. With nearly 300 square feet more than the typical Elua two-bedroom unit, you can spread out, relax and truly enjoy your stay in paradise. Our large lanai, …see more

from $425 / night

$2976 - $4816 / week

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from $425 / night

(1) Excellent 

23

Vacation villa with shared pool in Wailea

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Aloha Maui vacation planners, Welcome to beautiful Wailea, a Master Planned Community which ensures good community planning and utilizes design guidelines to help preserve Maui's sophisticated island environment. Grand Champions Villas is located in the heart of Waile …see more

from $225 / night

$1575 / week

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from $225 / night

(1) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting …see more

from $599 / night

$4193 - $9093 / week

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from $599 / night

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting …see more

from $519 / night

$3633 - $7175 / week

Inquire View

from $519 / night

(8) Excellent 

14

Vacation apartment in Wailea

Maui / Wailea

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
SUMMER SPECIAL: Stay 2 weeks in June/July for only $175/night. Simply request the special rate when you inquire. If you love to swim in the ocean, if you have kids who like to play in the sand and go wading, if you want to stroll on a beach holding hands as the sun set …see more

from $159 / night

$1299 - $1439 / week

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from $159 / night

(4) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Note from the Owner: Nothing Beats Living in Paradise; Catch that Mahalo Feeling. Picture yourself here! And a sigh escapes your lips as you walk through the door. Postcard Perfect 'South Pacific' sunsets await you. Swaying palm trees silhouetted against the ocean a bri …see more

from $383 / night

$2681 - $4816 / week

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from $383 / night

(14) Very Good 

16

Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting …see more

from $499 / night

$3493 - $7175 / week

Inquire View

from $499 / night

(5) Very Good 

16

Apartment accommodation in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf G-104 is a beautiful, ground floor condo that has a spacious lanai complete with its own BBQ. It opens to perfectly manicured grounds where you can enjoy the lawn and incredible views of the pacific ocean. Makena Surf Resort is a luxurious secluded beachfron …see more

from $540 / night

$3780 - $6475 / week

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from $540 / night

(20) Very Good 

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky shoreline fronting …see more

from $446 / night

$3122 - $5425 / week

Inquire View

from $446 / night

21

Condo rental in Wailea with shared pool, golf nearby

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
QUIET PRIVACY IN PARADISE This is a luxurious one-bedroom two-bath ground floor villa tucked away in a private and quiet corner in one of the nicest locations in the property. Often the only sound you will hear is the waves crashing on the nearby beaches. The Palms at …see more

from $189 / night

$1323 / week

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from $189 / night

27

Vacation apartment with shared pool in Wailea

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Wailea Ekahi Village #53C is a fully renovated, 2 bedroom / 2.5 bath townhouse with Ocean views from the upstairs bedrooms and private Garden views from the downstairs lanai. This LARGE townhouse has 1575 sq. feet of living space. The master bedroom suite offers a King …see more

from $465 / night

$3045 - $4305 / week

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from $465 / night

19

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! Wailea Ekolu 1606 is a top floor two bedroom two bath condo with a wonderful ocean view. Beautiful wood flooring throughout, vaulted ceilings, spectacular kitchen and classy island decor. The l …see more

from $270 / night

$1785 - $2520 / week

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from $270 / night

26

Vacation condo with shared pool in Wailea

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Mana Kai Maui Resort has been a fan favorite condo property in South Maui for decades. The property is so highly praised because of its superb location at the start of Keawakapu Beach. The white sand beach stretches for over a mile, right into Wailea, ending in fr …see more

from $335 / night

$2345 / week

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from $335 / night

1