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Wailea Vacation Rentals on the Island of Maui, Hawaii
Hawaii Vacation Rentals:
Wailea, Maui
The luxurious Wailea resort community is known for its upscale but informal lifestyle, crescent-shaped Maui beaches and challenging Maui golf courses. One of the finest planned communities in Hawaii, the world class 1,500 acre resort is only minutes from Kihei. Stroll the famous Wailea Beach Walk next to one of the best beaches in America. Pick from favorite designers at The Shops at Wailea. Experience our fine selection of Maui condos and more.
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FLASH SALE! Left to Save 18% 4/27 - 5/4!

Grand Champions 186 - 2 Bedrooms, 2nd Floor, Overlooking Pool

Grand Champions, Wailea, HI
2 BR, 2 BA, Sleeps 4,Pool View
This stunningly renovated condo has everything you need for an incredible Hawaiian vacation! With gorgeous pool views, TVs in every room, and resort amenities, you’ll love every moment you spend here.
Was $1,593.13
NOW $1,310.90

FLASH SALE! Left to Save 18% 4/27 - 5/4!

Grand Champions 78, 2 Bedrooms, Golf View, WiFi, Pool Access, Sleeps 4

Grand Champions, Wailea, HI
2 BR, 2 BA, Sleeps 4,Golf View
With a view of the golf course fairway and the Pacific Ocean to the west and of the Haleakala Volcano to the east, Grand Champions 78 is the ideal place to relax and enjoy the best of Maui. Your condo is far from roads and very quiet.
Was $1,441.72
NOW $1,186.32

FLASH SALE! Left to Save 18% 4/27 - 5/4!

Grand Champions 144 - 3 Bedrooms, Ocean and Golf Course Views, 2 Pools, Sleeps 6

Grand Champions, Wailea, HI
3 BR, 2 BA, Sleeps 6,Ocean View
Whether you are looking for a relaxing getaway or seeking adventure of all kinds, Maui is the perfect vacation spot! Grand Champions 144 is a three bedroom, two bathroom condo that sleeps six guests.
Only 3 weeks left in the next 60 days!
Was $2,273.46
NOW $1,870.72

Limited-Time Offer: Stay before 6/15/19 and Save Up to 19%!

Grand Champions 35, 2 Bedrooms, 3rd Floor, Ocean View, Pool, Sleeps 5

Grand Champions, Wailea, HI
2 BR, 2 BA, Sleeps 5,Ocean View
Palm trees swaying in the breeze, tropical air filling your senses, and a great ocean view are waiting for you in Maui Wailea. Grand Champions 35 is a two bedroom, two-bathroom condo that sleeps five guests.
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 19%!

Grand Champions 122, 1 Bedroom, Pool Access, Spa, WiFi, Sleeps 2

Grand Champions, Wailea, HI
1 BR, 2 BA, Sleeps 2,Ocean View
Few destinations are as romantic as Maui, and Grand Champions 122 is the perfect Maui condo for just the two of you. From your private balcony, which runs the length of the 1-bedroom unit, to the amazing amenities and close location to the beach, you ...
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 19%!

Palms at Wailea 1606 - 2 Bedrooms, Spacious Condo, Pool, Sleeps 6

Palms At Wailea, Wailea, HI
2 BR, 2 BA, Sleeps 6,Limited Ocean View
The lush scenery cannot be beat at Palms at Wailea 1606! This beautiful condo features two spacious bedrooms, two bathrooms and sleeps six.
Only 3 weeks left in the next 60 days!
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 16%!

Grand Champions 8 - 2 Bedrooms, Top Floor Private Lanai, Pool

Grand Champions, Wailea, HI
2 BR, 2 BA, Sleeps 4,Garden View
Palm trees swaying in the breeze, tropical air filling your senses, and a great ocean view are waiting for you in Maui! Grand Champions 8 is a two bedroom, two bathroom condo that sleeps four guests.
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 19%!

Wailea Ekolu 1610 - 2 Bedrooms, Renovated, Ocean View, 2 Pools, Sleeps 5

Wailea Ekolu, Wailea, HI
2 BR, 2.5 BA, Sleeps 5,Ocean View
Gaze at the sea from your private lanai at this stunning two-bedroom, two-story townhome! Treat yourself to fine living, high-end finishes, TVs in every room, and the best of Maui right outside your door.
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 19%!

Wailea Ekahi 17D - 1 Bedroom, 2nd Floor Panoramic Ocean Views, Pool

Wailea Ekahi, Wailea, HI
1 BR, 2 BA, Sleeps 4,Ocean View
Panoramic views of the Pacific Ocean, outer islands, and lush tropical foliage flood your lanai, living room, dining room, and kitchen when you vacation at Wailea Ekahi 17D in beautiful Wailea, Maui. You’re near beautiful Keauwakapu Beach, but with four pools ...
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 19%!

Wailea Ekahi 17B - 1 Bedroom, Ground Floor, Partial Ocean View, Pool

Wailea Ekahi, Wailea, HI
1 BR, 2 BA, Sleeps 4,Limited Ocean View
You’ll feel like you’re on a private island when you step out on your flower-strewn, covered lanai at Wailea Ekahi 17B. With a beautiful tropical and partial ocean view, this large covered lanai that extends the length of the condo will be a favorite ...
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK NOW!

Grand Champions 49 - 2 Bedrooms, Spacious Lanai, Remodeled, Pool

Grand Champions, Wailea, HI
2 BR, 2 BA, Sleeps 4,Garden View
Surround yourself with elegant furnishings, two pools, and incredible garden views, only a short way from some of the best beaches in Maui. This villa will be your home away from home in paradise!
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK NOW!

Wailea Ekahi 27B - 2 Bedrooms, Ocean View, Pool, Sleeps 6

Wailea Ekahi, Wailea, HI
2 BR, 2.5 BA, Sleeps 6,Ocean View
Ocean views from a second-story lanai off the master bedroom? New furnishings, a sleeper sofa, and gorgeous landscaping in all directions?
Only 2 weeks left in the next 60 days!
ONLY $300 TO BOOK NOW!

Wailea Ekolu 1205, 2 Bedrooms, WiFi, Ocean View, Pool Access, Sleeps 4

Wailea Ekolu, Wailea, HI
2 BR, 2 BA, Sleeps 4,Ocean View
Begin your day with an alfresco breakfast on your covered lanai while gazing out at palm trees and the azure Pacific Ocean. End your evening sprawled out on your king-size bed as the rhythmic pounding of the waves lulls you to sleep.
Only 3 weeks left in the next 60 days!
ONLY $300 TO BOOK NOW!

Palms At Wailea 606, 2 Bedrooms, Pool Access, WiFi, Sleeps 6

Palms At Wailea, Kihei, HI
2 BR, 2 BA, Sleeps 6,Limited Ocean View
Enjoy catching some rays on the balcony at Palms at Wailea 606! This beautiful condo features two spacious bedrooms, two bathrooms, and sleeps six.
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK NOW!

Wailea Ekahi 41B - 1 Bedroom, Ground Floor Beach Access, 4 Pools

Wailea Ekahi, Wailea, HI
1 BR, 2 BA, Sleeps 4,Ocean View
From Wailea Ekahi 41B’s garden level, covered lanai, enjoy a private getaway with fabulous ocean views, pool and cabana access, and the tropical flora that lie only steps away from the private ocean access. From this beautifully appointed condo, you can walk ...
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK NOW!

Grand Champions 181, 1 Bedroom, Sleeps 4, 2 Pools

Grand Champions, Wailea, HI
1 BR, 2 BA, Sleeps 4,Best Value/Garden
Grand Champions 181 is a spacious, ground floor condo with access to two community pools and a hot tub. Enjoy golfing or wading in the turquoise waters off some of Maui’s most spectacular beaches!
ONLY $300 TO BOOK NOW!

Ho'olei 39-3 - 3 Bedroom, Spacious Upscale Condo, Views, Pool, Sleeps 8

Ho'olei, Wailea, HI
3 BR, 3.5 BA, Sleeps 8,Ocean View
To call Ho’olei 39-3 “spectacular” doesn’t do this three-bedroom, two-story villa justice. From the luxurious furnishings to the awe-inspiring sunsets over the ocean visible from the spacious lanais, everything about this 2,700-square-foot haven is of a ...
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK NOW!

Wailea Ekahi 32B - 1 Bedroom, Ocean View, Access to 4 Pools

Wailea Ekahi, Wailea, HI
1 BR, 2 BA, Sleeps 2,Ocean View
Looking for the ultimate Maui experience? You owe it to yourself to stay at Wailea Ekahi 32B.
ONLY $300 TO BOOK NOW!

Wailea Ekahi 17E, 1 Bedroom, Ocean View Oversized Lanai, Pool

Wailea Ekahi, Wailea, HI
1 BR, 2 BA, Sleeps 2,Ocean View
The beauty of sand and sparkling waters and the warm Hawaiian sun is calling your name! Wailea Ekahi 17E is a one bedroom, two bathroom condo that sleeps two guests.
ONLY $300 TO BOOK NOW!

Wailea Ekahi 34B - 1 Bedroom, Updated Ocean View, Access to 4 Pools

Wailea Ekahi, Wailea, HI
1 BR, 2 BA, Sleeps 4,Ocean View
Four can stay comfortably in this exquisite vacation condo when the queen-sized sofa sleeper is put to use. From the moment you enter Wailea Ekahi 34B you’ll be drawn to its beautiful ocean and garden view.
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK NOW!

Grand Champions 108, 1 Bedroom, Cozy Lanai, Pool Access, Hot Tub, Sleeps 2

Grand Champions, Wailea, HI
1 BR, 2 BA, Sleeps 2,Garden View
Grand Champions 108 is made for romance. The balcony of the one-bedroom condo looks out over the complex’s lush grounds toward the Haleakala Mountains.
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK NOW!