50 Best Wailea Condos on Holiday Lettings - Vacation rentals

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173 Vacation rentals

(3) 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

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

(17) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Ask about children
  • Air conditioning
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

(9) Excellent 

16

Wailea Vacation apartment rental

Maui / Wailea

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Ask about children
NEW! For the First time in rental pool - Gorgeous and spacious ground floor 1 B/2BA condo, completely renovated in a contemporary style in 2017 is a 2 min walk to the world renowned Keawakapu beach, pools and pavilion. It has walk-out access to private well manicured gr …see more

from $269 / night

$1884 - $2695 / week

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from $269 / night

(4) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
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 $489 / night

$3424 - $7175 / week

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from $489 / night

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • 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

$3080 - $5950 / week

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from $440 / night

(8) Excellent 

19

Vacation apartment with shared pool in Wailea

Maui / Wailea

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! Relax in this spectacular three bedroom deluxe accommodation. Beautifully decorated, many exquisite art pieces and special touches create a warm inviting atmosphere. The living room features st …see more

from $810 / night

$6160 - $11165 / week

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from $810 / night

(13) Excellent 

17

Wailea Vacation apartment rental

Maui / Wailea

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! Grand Champions #35 is an inviting third floor, two bedroom, two bath, Ocean View condo. The living room has sofa and love seat, A/C, Large Flat Screen TV, and Blu-Ray player. The newly updated …see more

from $235 / night

$1645 - $2170 / week

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from $235 / night

(3) Excellent 

21

Vacation apartment with shared pool in Wailea

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’! Beautiful ocean views, swimming and snorkeling from the property, and a fully refurbished condominium awaits you at our Wailea Elua Village #2011. This one bedroom two bath is tiled throughout, …see more

from $385 / night

$2695 - $3326 / week

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from $385 / night

(8) Very Good 

16

Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
About this condo: Wailea Elua Village #1510 is a spacious two-bedroom, two-bath ocean view condo in located just a short walk away from the property's central pool, Jacuzzi and paddle tennis courts. Newly replaced carpet, living room furniture, granite counter tops and …see more

from $383 / night

$2681 - $4816 / week

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from $383 / night

(2) Very Good 

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’! Beautifully decorated and fully renovated two bedroom condominium with garden, some ocean and mountain views. Beautiful new tile floors throughout, designer painted, granite counters, new furni …see more

from $260 / night

$1820 - $2415 / week

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from $260 / night

(2) Excellent 

12

Wailea Vacation condo rental

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Tastefully remodeled, this two bedroom, two bath condominium has many upgrades including a new contemporary kitchen with granite counter tops and stainless steel appliances. The master bathroom and guest bathroom were beautifully remodeled in 2015. Vaulted ceilings in t …see more

from $245 / night

$1715 / week

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Responds fast!
avg. 3 hours 47 minutes

from $245 / night

(18) Excellent 

25

Vacation apartment in Wailea

Maui / Wailea

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • 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 $250 / night

$1700 - $2000 / week

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Responds fast!
avg. 2 hours 51 minutes

from $250 / night

(7) Excellent 

21

Vacation apartment with shared pool in Wailea

Maui / Wailea

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! Enjoy more than 2700 feet of comfortable yet lavish, uniquely and professionally decorated living space. The great room is aptly named with vaulted ceiling, HDTV, DVD, wireless internet and for …see more

from $810 / night

$6160 - $11165 / week

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from $810 / night

(3) Excellent 

17

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
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! Grand Champions 186 is located on the second floor and overlooks one of the 2 pools on property. Featuring a modern Hawaiian theme throughout. The living room has a large High Definition TV wit …see more

from $235 / night

$1645 - $2170 / week

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from $235 / night

(1) Very Good 

22

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 8 is a top floor tropical delight with lush foliage surrounding the lanai for privacy. There is a spacious airy feeling with vaulted ceilings and ceiling fans in the living area …see more

from $225 / night

$1575 - $2135 / week

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from $225 / night

18

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
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! Wailea Ekahi #27B offers Ocean views from the upstairs master bedroom Living area and Lanai. The master bedroom has a King bed, ocean view and en-suite bath. The guest bedroom has a new Queen b …see more

from $415 / night

$2905 - $3745 / week

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from $415 / 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
  • 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 $473 / night

$3311 - $6125 / week

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from $473 / 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 $270 / night

$1890 - $2766 / week

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from $270 / 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
  • Air conditioning
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

(4) Excellent 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

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

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
A Note from the Owner: We enjoy spending time out on the lanai, which has a large grassy area behind it that is great for our grandchildren to play ball on. Ulua beach is just a short walk and it's great for paddle boarding, boogie boarding and snorkeling. The Shops at …see more

from $383 / night

$2681 - $4816 / week

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from $383 / night

(17) Very Good 

16

Vacation apartment rental

Maui / Wailea

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Ask about children
  • Air conditioning
About this condo: Wailea Elua Village #1601 is an inviting ground floor one bedroom, two bath oceanfront condo plus sofa sleeper with a large wrap-around lanai: the perfect location for watching stunning Maui sunsets and enjoying the lush tropical landscaping. Imagine s …see more

from $420 / night

$2940 - $5586 / week

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from $420 / night

(1) Excellent 

15

Apartment rental in Wailea with golf nearby

Maui / Wailea

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Gorgeous ocean views and just steps from the beach. Our large 2 bedroom, 2 bath condo features over 40' of windows/doors with panoramic ocean and island views. Both bedrooms are ensuite and have king size beds and refined Hawaiian furnishings. Watch sunsets and whale …see more

from $700 / night

$4900 / week

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Responds fast!
avg. 51 minutes

from $700 / 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 $129 / night

$903 / week

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from $129 / night

(13) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
A note from the owner: Welcome to Grand Champions #180, our Maui getaway that comes complete with all the comforts and conveniences of home. We invite you to enjoy this 3 bedroom, 2 bath with your family and friends. You'll love the ocean view beyond Wailea's world clas …see more

from $250 / night

$1750 - $3465 / week

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from $250 / 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 $315 / night

$2205 - $2766 / week

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from $315 / 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
  • Air conditioning
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

$8163 - $12594 / week

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from $1166 / night

16

Vacation apartment in Wailea

Maui / Wailea

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • 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

$3080 - $5950 / week

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from $440 / night

(11) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • 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

(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 $612 / night

$4284 - $7175 / week

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from $612 / 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 $235 / night

$1645 - $2170 / week

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from $235 / 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

(18) Very Good 

14

Wailea Vacation apartment rental

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
Discounted Rates Available for the Summer of 2017 - Promo Code: ‘HOTSUMMER’! A spacious two bedroom / two bath condominium in beautiful Wailea. A partial ocean view, BBQ grill and comfortable lanai furniture to enjoy while relaxing in tropical breezes. The kitchen is we …see more

from $220 / night

$1540 - $2030 / week

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from $220 / 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 $325 / night

$2275 - $2766 / week

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from $325 / night

(1) Excellent 

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • 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 $620 / night

$4340 - $10493 / week

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from $620 / night

(3) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • 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 $600 / night

$4200 - $7175 / week

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from $600 / night

23

Vacation villa in Wailea

Maui / Wailea

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Tropical paradise is made even more magical with this luxury vacation rental. With a third story location that has views of the Pacific and ample entertaining space both indoors and out, we're certain your Maui vacation will be unforgettable. The open floor plan feature …see more

from $1799 / night

$12594 - $26593 / week

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from $1799 / 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

(11) Excellent 

70

Vacation apartment in Wailea

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
2-5 Bedroom, on the sand in front of the Fairmont Kea Lani in Wailea / Makena Maui, Hawaii. Features: Beach Front - On the Sand! Snorkeling. Central Air conditioning We have correct HOTEL ZONING for Maui vacation rentals Sleeps 6 Two elevators By Owner Beachfron …see more

from $350 / night

$2450 / week

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from $350 / night