50 Best Wailea Condos on Holiday Lettings - Vacation rentals

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900 Vacation rentals

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

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

$2,681 - $4,816 / 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
  • Ask about pets
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 $419 / night

$2,933 - $5,103 / week

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from $419 / 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 $198 / night

$1,386 - $2,380 / week

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from $198 / 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 $540 / night

$3,780 - $6,475 / week

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from $540 / 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

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from $266 / night

(8) Very Good 

16

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 - $6,475 / week

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from $486 / 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 - $3,290 / week

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from $293 / night

20

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 - $5,950 / 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
  • 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

(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
  • Ask about pets
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

$4,284 - $7,175 / week

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from $612 / 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 $110 / night

$805 - $1,393 / week

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Responds fast!
avg. 3 hours 30 minutes

from $110 / 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
  • Ask about pets
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

$2,681 - $4,816 / week

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from $383 / night

16

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
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

$3,780 - $6,475 / week

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from $540 / night

(10) 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
  • Ask about pets
A Note from the Owner: We chose Maui as the prefect location for our second home based on year around outstanding weather. Every day has highs in the 80s and generally bright sunshine. Our favorite hobby is golf. There are 5 courses within a few miles radius of Ekolu. O …see more

from $250 / night

$1,750 - $2,688 / week

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from $250 / night

16

Vacation apartment in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets
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 $490 / night

$3,430 - $6,300 / week

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from $490 / 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
  • Ask about pets
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

$2,681 - $4,816 / week

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from $383 / 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
  • Ask about pets
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 $1,166 / night

$8,162 - $12,593 / week

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from $1,166 / 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
  • Ask about pets
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 $540 / night

$3,780 - $6,475 / week

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from $540 / night

15

Vacation villa in Wailea

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

(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
  • 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 $699 / night

$4,893 - $9,093 / week

Inquire View

from $699 / 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 $612 / night

$4,284 - $7,175 / week

Inquire View

from $612 / 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
  • Ask about pets
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

$2,625 - $4,431 / week

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from $375 / 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 - $5,950 / week

Inquire View

from $440 / 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 $267 / night

$1,869 - $3,465 / week

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from $267 / 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

(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
  • Ask about pets
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

$4,284 - $7,175 / week

Inquire View

from $612 / 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
  • Ask about pets
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

$2,975 - $4,816 / week

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from $425 / night

(7) Excellent 

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 $383 / night

$2,681 - $4,816 / week

Inquire View

from $383 / night

(14) Very Good 

16

Vacation apartment rental

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • 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 $612 / night

$4,284 - $7,175 / week

Inquire View

from $612 / 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 $446 / night

$3,122 - $5,425 / week

Inquire View

from $446 / 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
  • 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 $612 / night

$4,284 - $7,175 / week

Inquire View

from $612 / 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
  • Ask about pets
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

$2,681 - $4,816 / week

Inquire View

from $383 / 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

(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
  • 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 $775 / night

$5,425 - $10,493 / week

Inquire View

from $775 / 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

(16) Excellent 

16

Apartment rental in Wailea

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 - $4,816 / week

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from $383 / night

(3) Excellent 

36

Vacation condo with shared pool in Wailea

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $380 / night

$2,660 / week

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from $380 / night

20

Vacation condo with shared pool in Wailea

Maui / Wailea

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
ATTENTION BEACHLOVERS: our 2 bedroom – 2 bath condo is just across the street from two of Maui’s best south shore beaches (Charley Young and Kamaole 1). Charley Young beach has awesome volcanic rock formations, and there are restrooms and lifeguards stationed just down …see more

from $175 / night

$1,225 / week

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from $175 / 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) 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 8 minutes

from $190 / night