50 Best Wailea Condos on Holiday Lettings - Vacation rentals

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926 Vacation rentals

25

Vacation condo with shared pool in Wailea

Maui / Wailea

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly
Newly remodeled with tile floors, bath and kitchen, this popular fully furnished vacation rental features a nice ocean view from a good sized lanai, custom kitchen equipped with all the kitchen wares and appliances you need. Very clean, attention to detail in every room …see more

from $99 / night

$693 / week

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from $99 / 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
  • Ask about pets
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 $292 / night

$2,044 - $3,465 / week

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from $292 / night

31

Vacation condo rental

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
FREE HIGH SPEED WIRELESS INTERNET AND UNLIMITED PHONE CALLS TO US MAINLAND AND CANADA!! Experience island life in our luxurious, spacious, one-bedroom Condo at Wailea Grand Champion Villas. Steve and Tamara are intent on providing you with the ultimate vacation rental …see more

from $150 / night

$1,050 / week

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Responds fast!
avg. 3 hours 10 minutes

from $150 / night

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets
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

$3,080 - $6,643 / week

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from $440 / night

(1) Excellent 

23

Vacation condo with shared pool, golf nearby in Wailea

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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

$1,393 / week

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from $199 / night

(1) Very Good 

24

Apartment rental in Wailea with shared pool

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Imagine yourself sitting on the lanai with a drink in hand, watching the gorgeous colors of the Hawaiian sunset! This is a perfect budget getaway. Come explore the island! See gorgeous beaches, taste the island cuisine, shop the local businesses and unwind to the magic …see more

from $115 / night

$805 - $1,393 / week

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from $115 / night

26

Condo rental in Wailea with shared pool

Maui / Wailea

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
This Hawaiian Themed Pacific Shores condo has all the bells and whistles and more. Central Air, granite counter tops, beautiful travertine flooring throughout, top of the line appliances, and Bosch washer dryer complement the completely upgraded remodel. There are two T …see more

from $149 / night

$1,043 / week

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from $149 / night

23

Vacation condo accommodation

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautifully furnished newly remodeled two bedroom, two bath luxury condo located in Maui Kamaole complex; Kihei's newest first class resort property. Nestled in the center of the sunny South Maui coast, Maui Kamaole is located across the street from famed Kamaole III Be …see more

from $225 / night

$1,575 - $2,800 / week

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from $225 / night

(1) Excellent 

25

Vacation condo rental

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Beautifully furnished and well appointed, with gorgeous views and 3 large Lanais. This is a very comfortable "home away from home" with many special amenities, full kitchen and BBQ. Newly remodeled and next to the Quiet Upper Pool, it is private, quiet and very spaciou …see more

from $385 / night

$2,695 - $3,045 / week

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from $385 / night

16

Apartment accommodation in Wailea

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Notes from the Owner: Come relax in the luxury and tropical splendor of Maui's premier resort, Wailea. Featuring miles of pristine beaches, magnificent sunsets and renowned cuisine, Wailea will surely be your ultimate vacation experience! The active vacationer can tee i …see more

from $189 / night

$1,323 - $2,380 / week

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from $189 / night

16

Vacation apartment in Wailea

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Ask about pets
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 $293 / night

$2,051 - $3,843 / week

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from $293 / night

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets
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

$3,080 - $6,643 / week

Inquire View

from $440 / 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
  • Ask about pets
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 $496 / night

$3,472 - $5,775 / week

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from $496 / night

(19) 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 $189 / night

$1,700 / week

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Responds fast!
avg. 3 hours 2 minutes

from $189 / night

(1) Excellent 

23

Wailea Vacation condo rental

Maui / Wailea

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This amazing newly renovated two bedroom condo has breathtaking ocean views, brand-new everything including appliances and top of the line luxury mattresses and bedding! Located on the fifth floor giving you stellar ocean views. The property is oceanfront situated on o …see more

from $550 / night

$3,850 / week

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from $550 / night

(13) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $220 / night

$1,540 / week

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from $220 / night

32

Villa rental in Wailea with shared pool

Maui / Wailea

3 8 6 nights min

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Come relax and enjoy the good life at our spectacular ocean-view luxury villa, located directly across from the Grand Wailea Hotel & Spa on the beautiful island of Maui. Situated on the third row at Ho'olei, this beautiful two-story villa boasts dramatic Pacific Ocean …see more

from $775 / night

$5,425 / week

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from $775 / night

(1) 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

$1,300 - $1,580 / week

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Responds fast!
avg. 2 hours 9 minutes

from $190 / night

(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 $1,100 / night

$7,700 / week

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from $1,100 / night

30

Vacation condo with golf nearby in Wailea

Maui / Wailea

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Child friendly
Summary What an exceptional find for the bargain hunter who doesn’t want to sacrifice a near perfect location! Situated between the North and South ends of Kihei’s two highest rated beaches, it is also just a minute from Wailea where the very best beaches in the world a …see more

from $129 / night

$903 / week

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from $129 / night

10

Wailea Vacation condo rental

Maui / Wailea

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child friendly
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 $175 / night

$1,225 / week

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from $175 / night

(7) Very Good 

16

Wailea Vacation apartment rental

Maui / Wailea

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
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 $662 / night

$4,634 - $7,525 / week

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from $662 / 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
  • Ask about pets
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

$3,675 - $4,865 / week

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from $525 / night

(16) Excellent 

16

Apartment rental in Wailea

Maui / Wailea

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Ask about children
  • Ask about pets
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

$2,681 - $5,593 / week

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from $383 / night

(10) Excellent 

Certificate of Excellence

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
This two-bedroom condo unit was awarded a Certificate of Excellence from TripAdvisor in 2017 for service quality and customer satisfaction. Best for families, such as parents with up to 6 children, for a combination of grandparents, parents and kids, or for two couples …see more

Certificate of Excellence

from $175 / night

$1,225 - $1,439 / week

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Responds fast!
avg. 1 hour 23 minutes

from $175 / night

(3) Excellent 

14

Vacation condo in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Maui Kamaole G-212 is a spacious and elegantly appointed condo with an incredible "Aloha" oceanfront view and a great location near all of the spectacular south Maui beaches. From the lanai, you look out on the beautiful Kamaole Beach III--a fabulous swimming, boogie b …see more

from $219 / night

$1,533 / week

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from $219 / 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
  • Ask about pets
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 $529 / night

$3,703 - $6,825 / week

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from $529 / night

(10) Excellent 

16

Wailea Vacation apartment rental

Maui / Wailea

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Ask about children
  • Ask about pets
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 $299 / night

$2,093 - $2,695 / week

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from $299 / 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
  • Ask about pets
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 $589 / night

$4,123 - $7,525 / week

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from $589 / night

15

Apartment rental in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
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 $486 / night

$3,402 - $6,825 / week

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from $486 / night

15

Vacation villa in Wailea

Maui / Wailea

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 2BR/2BA Condo in Wailea located in the amazing Grand Champions Villas complex. Only a 5 minute walk to the beach, Grand Champions provides a luxurious, relaxed vibe in the beautiful town of Wailea. Close to numerous restaurants, shops and beaches. Relax in t …see more

from $175 / night

$1,225 / week

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from $175 / 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
  • Ask about pets
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

$1,750 - $3,465 / week

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from $250 / night

(3) Excellent 

36

Vacation condo with shared pool in Wailea

Maui / Wailea

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Wailea Ekahi 20F is a 2 bedroom unit featuring panoramic ocean views, a great, quiet location with a short, 2 minute walk to Keawakapu Beach. As new owners, we welcome you to enjoy our condo and all that it has to offer! Wailea Ekahi Village is a premier ocean front c …see more

from $425 / night

$2,975 / week

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from $425 / night

24

Vacation condo in Wailea

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sometimes I feel like our guests say it best. Here is one of my recent guest book entries: 'We just enjoyed two weeks of complete relaxation at this wonderful condo unit in the best complex we have stayed at in Maui. The view from the living room and lanai is outstand …see more

from $120 / night

$700 - $2,240 / week

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from $120 / night

34

Condo accommodation in Wailea

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Unit: Beachfront Bliss | Maui Guidebook Summary Direct beachfront unit in very small (12 unit total) condo building. Unit 6 is an end unit, tucked away on the quiet Northern side of the building for the most privacy. This is the way it used to be before Kihei was devel …see more

from $295 / night

$2,065 / week

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from $295 / night

(5) Very Good 

82

Apartment rental in Wailea with shared pool, golf nearby

Maui / Wailea

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • 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 $175 / night

$1,225 / week

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Responds fast!
avg. 2 hours 51 minutes

from $175 / 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
  • Ask about pets
Wailea Grand Champions Golf Villas is a modern property located between the Wailea Blue Golf Course and the Wailea Tennis Club. This quiet low density development consists of twenty mostly two-story buildings set amongst lush tropical landscaping and is a convenient sho …see more

from $200 / night

$1,400 - $3,073 / week

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from $200 / night

(1) Excellent 

16

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

$1,575 / week

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Responds fast!
avg. 3 hours 35 minutes

from $225 / night

(3) Very Good 

16

Vacation apartment in Wailea

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Ask about pets
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 $266 / night

$1,862 - $3,045 / week

Inquire View

from $266 / night

(4) Excellent 

17

Vacation apartment rental

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
Total renovation with high end finishes. All amenities: AC, HDTVs, free phone calls to US & Canada, free WIFI, Stainless Steel appliances, granite counters. Located in the upper part of Ekahi Village, an Ocean-Front community located on Keawakapu Beach, Wailea, South Ma …see more

from $220 / night

$1,540 / week

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from $220 / night