50 Best Wailea Condos on Holiday Lettings - Vacation rentals

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139 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 $199 / night

$1390 - $1900 / week

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Responds fast!
avg. 2 hours 43 minutes

from $199 / night

(1) Excellent 

24

Vacation villa with golf nearby in Wailea

Maui / Wailea

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

(6) Excellent 

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
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 $383 / night

$2681 - $4816 / week

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from $383 / 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 $139 / night

$973 / week

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from $139 / 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
  • Air conditioning
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) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
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

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
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

$3081 - $5950 / week

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from $440 / night

(16) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
A note from the owner: You will love the elegance of this remodeled one-bedroom, two-bath Elua condo. You can spread out, relax and truly enjoy your stay in paradise. Our large lanai, living room and master bedroom are ocean facing, with a spectacular panorama of ocean …see more

from $375 / night

$2625 - $4431 / week

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from $375 / night

(1) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
You will immediately sense that the fabulous Maui vacation you have been looking forward to has begun when you step into this completely remodeled 2 bedroom, 2 bath condo located on one of the best locations in the Wailea Elua Village. From our condo you can enjoy a stu …see more

from $440 / night

$3081 - $5950 / week

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from $440 / 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
  • Air conditioning
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

(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
  • Air conditioning
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

(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
  • Air conditioning
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 $500 / night

$3493 - $7175 / week

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from $500 / 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
  • Air conditioning
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 $579 / night

$4054 - $7175 / week

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from $579 / night

(5) Excellent 

15

Vacation apartment with shared pool in Wailea

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! All New Upgraded Kitchen and Baths. Grand Champions 54 offers a large 54" flat screen TV, DVD player, CD player, iPod dock, free high speed WiFi access. The living room has air conditioning, ce …see more

from $215 / night

$1400 - $1856 / week

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from $215 / 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
  • Air conditioning
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 $680 / night

$4760 - $7175 / week

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from $680 / 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
  • Air conditioning
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 - $6476 / week

Inquire View

from $540 / 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

(16) Excellent 

16

Apartment rental in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
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

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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 - $7175 / week

Inquire View

from $599 / 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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Responds fast!
avg. 3 hours 27 minutes

from $225 / 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
  • Air conditioning
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 $699 / night

$4893 - $10493 / week

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from $699 / 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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Responds fast!
avg. 2 hours 4 minutes

from $220 / night

(2) Excellent 

20

Wailea Vacation apartment rental

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! This beautifully updated condominium offers ocean views and greenbelt views. It has a King bed in the bedroom, Queen pull out sofa sleeper in the living room, air conditioning in the living roo …see more

from $310 / night

$1995 - $2590 / week

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from $310 / night

16

Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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 - $6476 / week

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from $540 / 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 - $2766 / week

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from $335 / night

(2) Very Good 

19

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’! Grand Champions 163 is a delightful ground floor two bedroom tiled throughout with the exception of the bedrooms. Beautiful, Kitchen and Vanity Cabinets with Granite Counter tops. The Living ro …see more

from $260 / night

$1645 - $2170 / week

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from $260 / night

(4) Excellent 

19

Wailea Vacation apartment rental

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Come enjoy condominium living at its finest at Wailea Ekahi #17D. Located in the heart of Wailea, Maui - is a One bedroom, Two bathroom deluxe condominium on the 2nd floor with panoramic ocean views. Enjoy fabulous ocean and outer island views from the living room, dini …see more

from $346 / night

$2275 - $2766 / week

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from $346 / night

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
Wailea Elua Village #2010 is located on one of the buildings corners, giving you ocean views and property from the master lanai and the main lanai which may also be accessed via the guest bedroom. Recently added to the condo area large new flat screen TV, iPod docking s …see more

from $383 / night

$2681 - $4816 / week

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from $383 / night

(1) Excellent 

23

Vacation condo with shared pool, golf nearby in Wailea

Maui / Wailea

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Air conditioning
Unit: Wailea Ekolu 507 | Maui Guidebook Summary Sweeping ocean and breathtaking neighbor island views from the living, dining, kitchen, bedroom and both lanais. Private ground floor corner location. Minutes from the very best beaches in Maui. Minutes from both luxury a …see more

from $199 / night

$1393 / week

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from $199 / night

(3) Very Good 

16

Wailea Vacation apartment rental

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! Grand Champions 118 is an inviting and cozy two bedroom two bath condominium. The kitchen and both baths have been remodeled Spring 2013!! The condo has air conditioning, ceiling fans, a 54" fl …see more

from $285 / night

$1750 - $2380 / week

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from $285 / 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 $691 / night

$4515 - $5846 / week

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from $691 / night

16

Vacation apartment in Wailea

Maui / Wailea

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children
Wailea Ekolu Village is a tranquil terraced property located on the Wailea Blue Golf Course offering distant panoramic views of the Pacific. This quiet low density village consists of eighteen two-story buildings spread out over 18 acres of tropical landscaping and is c …see more

from $267 / night

$1870 - $3465 / week

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from $267 / night

(2) Excellent 

15

Vacation apartment in Wailea

Maui / Wailea

2 8 4 nights min

  • 2 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 1 mi
  • Child friendly
Our spacious Wailea Ekolu Condominium is fully appointed and includes phone, radio, CD/DVD player, cable TV, and WiFi Internet connection. Three flat screen TVs have been installed. Personal touches for your enjoyment and convenience. This unit is a 2,000-square-foot to …see more

from $190 / night

$1300 - $1580 / week

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Responds fast!
avg. 1 hour 44 minutes

from $190 / night

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
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

$3081 - $5950 / week

Inquire View

from $440 / night

(22) Very Good 

16

Wailea Vacation apartment rental

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning
About this condo: Wailea Elua Village #1402 is a 2nd story, one bedroom, one bath oceanfront condo complete with a fully remodeled kitchen, new carpet and a sofa sleeper. Enjoy the complimentary wireless internet service on your lanai as you enjoy the beautiful view of …see more

from $525 / night

$3675 - $4865 / week

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from $525 / night

26

Vacation condo 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 fron …see more

from $335 / night

$2345 / week

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from $335 / night

(3) Very Good 

82

Apartment rental in Wailea with shared pool, golf nearby

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
We are pleased to offer our new 1 bedroom,1 bath upper level condo for rental. It has been redecorated throughout, is newly furnished and equipped to high standards, is very comfortable and located in well maintained lush Ekahi Village. The condo is close to the best of …see more

from $195 / night

$1365 / week

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from $195 / night

(2) Very Good 

20

Apartment rental in Wailea with shared pool

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! This condominium home has been beautifully upgraded throughout and boasts a wonderful kitchen, dining room and living room. New carpet was added throughout and new living room furniture greets …see more

from $346 / night

$2275 - $2766 / week

Inquire View

from $346 / night

(11) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
Notes from the Owners: Wailea Elua Village #1204 is a beautiful two bedroom, two bath oceanfront condo that has been fully remodeled with top of the line appliances and the latest in furnishings. The large travertine flooring in the kitchen, dining, living and baths pro …see more

from $599 / night

$4193 - $8400 / week

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from $599 / night

1