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A dreamy resort location, safe and accessible to everything an island vacation should offer, our Wailea vacation rentals on Maui’s south shore are a perfect pick, equally for couples or families. The upscale resort area provides continuous captivating scenery. Also consider our 63 Wailea condos and 80 Wailea luxury rentals.
Wailea vacation rentals 1 - 10 of 61
3 Bedrooms, 3 Baths, Sleeps 6
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CLICK HERE FOR A VIRTUAL TOURThe “crown jewel” of Wailea- A gated beachfront location, an oceanfront adult pool with a Jacuzzi, a children’s pool with a Jacuzzi in a garden setting- all with... Read More
3 Bedrooms, 3 Baths, 1 Half Bath, Sleeps 8
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Spend countless hours enjoying this 3 bedroom, 3 and one half bath Ocean view Villa while sitting birdâs eye view to the most amazing ocean and facing direct to the Alalakeiki Channel... Read More
4 Bedrooms, 4 Baths, 1 Half Bath, Sleeps 8
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The Wailea Sunset Estate may be rented in combination with the adjoining Wailea Sunset Bungalow for a total of as many as 6 bedrooms and 6.5 baths for up to 16 guests. The Wailea Sunset Estate is a... Read More
3 Bedrooms, 3 Baths, Sleeps 7
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African mahogany detailing, extensive use of marble & granite, nine foot ceilings, luxurious silk draperies, stereo surround sound, and four flat screen TVs add to the sophisticated elegance of... Read More
3 Bedrooms, 3 Baths, Sleeps 6
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Experience a level of luxury and service unlike anything you've ever encountered. Wailea Beach Villas' private vacation rentals offer our guests the comfort and privacy of magnificent private homes,... Read More
3 Bedrooms, 3 Baths, Sleeps 6
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This 3 bedroom, 3 bath penthouse has a beautiful 900 square foot wraparound lanai with completely retractable sliding glass doors so that the commanding view can be enjoyed from inside as well as... Read More
3 Bedrooms, 3 Baths, 1 Half Bath, Sleeps 6
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Experience a level of luxury and service unlike anything you've ever encountered. Wailea Beach Villas' private vacation rentals offer our guests the comfort and privacy of magnificent private homes,... Read More
2 Bedrooms, 2 Baths, Sleeps 4
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Experience a level of luxury and service unlike anything you've ever encountered. Wailea Beach Villas' private vacation rentals offer our guests the comfort and privacy of magnificent private homes,... Read More
3 Bedrooms, 3 Baths, Sleeps 6
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This three bedroom, three bath penthouse has a beautiful 900 square foot wraparound lanai with retractable sliding glass doors which makes the connection between the indoors and outdoors seamless.... Read More
3 Bedrooms, 3 Baths, Sleeps 6
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WBV Penthouse 105 is an artistic delight. This 3 bedroom beautiful spacious ground floor unit offers a king bed in the master bedroom, king bed in the second bedroom and a queen bed in the third... Read More
Wailea vacation rentals 1 - 10 of 61
If you obtain a lower rate within 24 hours of paying for your booking, we will refund the difference!
Things To Do
Wailea Beach is ideal for swimming and a pleasant day at the beach. Polo Beach is good for both swimming and snorkeling as well as hanging out for the day, in part thanks to its facilities, including restrooms/showers, picnic tables, barbecue grills, and a paved parking lot. Keawakapu Beach is a bit more remote, without the amenities. Interesting, and strange, are the junk cars that form a man-made reef for divers. The cars were placed to attract sea life for fisherman, but it didn’t quite work that way and is instead attractive, and useful, to divers.Golfers staying at a Wailea vacation rental have their pick of Wailea’s courses, the Blue, Emerald and Gold.
Each offers a different facet of the terrain, whether tropical or rugged. Preserved historic lava rock is incorporated into the Gold course and all are challenging and worthy of a couple rounds.
Eat and Shop
Upscale restaurants and casual eateries with an island flair are all options nearby our Wailea rentals. Fresh seafood is plentiful on the south shore and nearby Kihei is home to conventional grocery stores.Expert shoppers will enjoy an escape to The Shops at Wailea for classic retail therapy, with opportunities to grab a meal and some cocktails. Ongoing events include island music and dance performances.
Getting Around
Maui County has public bus transportation, but renting a car is best for exploring the south shore and for the convenience of moving about freely.Latest Wailea Articles
Current blog posts about Wailea or visit our complete archive.- Maui Zip Line Tours - 8.31.10
Exhilaration, pineapples, sunset or moonlight zip lines, long ziplines that begin in one town and end in another—what more could a thrill seeker want? Enjoy the ride Generally, if you’re 10 years of age and weigh at least 60 lbs, you can experience a zipline tour. The tour begins when you board an open air four wheel drive for a ride through sugar cane fields and the Waikapu Valley toward the zip line destination. - Haleakala Volcano Tours Delight Maui Visitors - 8.25.10
The top attraction on Maui is Mt. Haleakala and a journey to see this astounding volcano is an unforgettable Hawaiian vacation experience. - Maui Fine Dining - 8.19.10
Lahaina Lahaina offers many fine dining options Fine dining in Lahaina is found at the Lahaina Grill (667-5117) where Pacific Rim cuisine is served. The Lahaina Grill is located just off of Front Street on Lahainaluna Road and serves a variety of tropical fare to delight the palate. - Shops at Wailea - 8.5.10
Find favorite shops and plenty to do at the Shops at Wailea, with the ocean minutes away. Browse and enjoy more than 60 stores, art galleries and eateries, plus take in live entertainment and specials. - Maui Luxury Destinations - 7.31.10
One of the best resources at HawaiianBeachRentals. com are the booking agents.
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Hundreds of vendors list their properties on our site. Hawaiian Beach Rentals is a listing and marketing company. Therefore, all pricing and terms of rental are determined by the individual vendor and are subject to change. All travelers must pay a 30% to 50% deposit to make a reservation and pay the full balance for the vacation rental within 30 to 100 days of arrival depending on the specific rental. Cancellation after a vacation rental confirmation is issued results in forfeiture of any collected money, except the guest's security deposit and cleaning fee (if applicable). Hawaiian Beach Rentals prides itself on outstanding customer service and listing the highest quality accommodations possible. For information on Vacation Rental Travel Insurance Click Here.