Welcome to the ultimate in Wailea luxury accommodations. Here at Hawaiian Beach Rentals, we've put together an array of the most luxurious Hawaii vacation rental properties that are located in the best areas, boast the most comfortable features, and display a raw splendor unique to the Hawaiian Islands. Also consider our 61 Wailea vacation rentals and 66 Wailea condos.
Wailea luxury rentals 1 - 10 of 38   
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Wailea condos. 3 Bedrooms, 3 Baths, 1 Half Bath, Sleeps 6, Townhouse, Community Pool, Hot Tub, Pool View, Ocean View, Beach: Beachfront, Internet Access Vacation at the Wailea Beach V...
3 Bedrooms, 3 Baths, 1 Half Bath, Sleeps 6
  • Townhouse
  • Community Pool
  • Hot Tub
  • Pool View
  • Ocean View
  • Beach: Beachfront
  • Internet Access
Vacation at the Wailea Beach Villas and you don't have to be unnecessarily concerned about the availability of lounge chairs or sun umbrellas. There is no need to spend extra money to rent a cabana... Read More
Rates
$3025 to $4500 / night
Wailea rentals. 3 Bedrooms, 3 Baths, 1 Half Bath, Sleeps 8, Villa, Heated Pool, Hot Tub, Ocean View, Beach: 5 min walk to Wailea Beach, Shopping: 1 min walk to Shops At Wailea, Sports: 5 min drive to Wailea Golf and Tennis, Adventure: 25 min drive to Maui Ocean Center, High Speed Internet Access, Wireless Internet Spend countless hours enjoying...
3 Bedrooms, 3 Baths, 1 Half Bath, Sleeps 8
  • Villa
  • Heated Pool
  • Hot Tub
  • Ocean View
  • Beach: 5 min walk to Wailea Beach
  • Shopping: 1 min walk to Shops At Wailea
  • Sports: 5 min drive to Wailea Golf and Tennis
  • Adventure: 25 min drive to Maui Ocean Center
  • High Speed Internet Access
  • Wireless Internet
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 between... Read More
Rates
$2750 / night
Wailea rentals. 4 Bedrooms, 4 Baths, 1 Half Bath, Sleeps 8, Private Home, Pool, Ocean View, Beach: Beachfront, Internet Access The Wailea Sunset Estate may b...
4 Bedrooms, 4 Baths, 1 Half Bath, Sleeps 8
  • Private Home
  • Pool
  • Ocean View
  • Beach: Beachfront
  • Internet Access
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
Rates
$1500 to $4000 / night
Special Rate
Guest Rating:
Wailea rentals. 3 Bedrooms, 3 Baths, Sleeps 7, Villa, Community Pool, Jacuzzi, Community Hot Tub, Garden View, Beach: 5 min walk to Wailea Beach, Shopping: 1 min walk to Shops At Wailea, Sports: 5 min drive to Wailea Golf and Tennis, Adventure: 25 min drive to Maui Ocean Center, High Speed Internet Access, Wireless Internet African mahogany detailing, ex...
3 Bedrooms, 3 Baths, Sleeps 7
  • Villa
  • Community Pool
  • Jacuzzi
  • Community Hot Tub
  • Garden View
  • Beach: 5 min walk to Wailea Beach
  • Shopping: 1 min walk to Shops At Wailea
  • Sports: 5 min drive to Wailea Golf and Tennis
  • Adventure: 25 min drive to Maui Ocean Center
  • High Speed Internet Access
  • Wireless Internet
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
Rates
$2400 / night
Wailea rentals. 3 Bedrooms, 3 Baths, Sleeps 6, Villa, Community Pool, Jacuzzi, Community Hot Tub, Ocean View, Beach: 5 min walk to Wailea Beach, Shopping: 1 min walk to Shops At Wailea, Sports: 5 min drive to Wailea Golf and Tennis, Adventure: 25 min drive to Maui Ocean Center, High Speed Internet Access, Wireless Internet Experience a level of luxury a...
3 Bedrooms, 3 Baths, Sleeps 6
  • Villa
  • Community Pool
  • Jacuzzi
  • Community Hot Tub
  • Ocean View
  • Beach: 5 min walk to Wailea Beach
  • Shopping: 1 min walk to Shops At Wailea
  • Sports: 5 min drive to Wailea Golf and Tennis
  • Adventure: 25 min drive to Maui Ocean Center
  • High Speed Internet Access
  • Wireless Internet
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
Rates
$2300 / night
Wailea rentals. 3 Bedrooms, 3 Baths, Sleeps 6, Villa, Community Pool, Jacuzzi, Community Hot Tub, Ocean View, Beach: 5 min walk to Wailea Beach, Shopping: 1 min walk to Shops At Wailea, Sports: 5 min drive to Wailea Golf and Tennis, Adventure: 25 min drive to Maui Ocean Center, High Speed Internet Access, Wireless Internet This 3 bedroom, 3 bath penthou...
3 Bedrooms, 3 Baths, Sleeps 6
  • Villa
  • Community Pool
  • Jacuzzi
  • Community Hot Tub
  • Ocean View
  • Beach: 5 min walk to Wailea Beach
  • Shopping: 1 min walk to Shops At Wailea
  • Sports: 5 min drive to Wailea Golf and Tennis
  • Adventure: 25 min drive to Maui Ocean Center
  • High Speed Internet Access
  • Wireless Internet
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
Rates
$2200 / night
Wailea rentals. 3 Bedrooms, 3 Baths, 1 Half Bath, Sleeps 6, Villa, Community Pool, Jacuzzi, Community Hot Tub, Garden View, Beach: 5 min walk to Wailea Beach, Shopping: 1 min walk to Shops At Wailea, Sports: 5 min drive to Wailea Golf and Tennis, Adventure: 25 min drive to Maui Ocean Center, High Speed Internet Access, Wireless Internet Experience a level of luxury a...
3 Bedrooms, 3 Baths, 1 Half Bath, Sleeps 6
  • Villa
  • Community Pool
  • Jacuzzi
  • Community Hot Tub
  • Garden View
  • Beach: 5 min walk to Wailea Beach
  • Shopping: 1 min walk to Shops At Wailea
  • Sports: 5 min drive to Wailea Golf and Tennis
  • Adventure: 25 min drive to Maui Ocean Center
  • High Speed Internet Access
  • Wireless Internet
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
Rates
$2100 / night
Wailea rentals. 3 Bedrooms, 3 Baths, Sleeps 6, Condo, Pool, Jacuzzi, Community Hot Tub, Garden View, Beach: 5 min walk to Wailea Beach just infront of property, Shopping: 1 min walk to Shops At Wailea, Sports: 5 min drive to Wailea Golf and Tennis, Adventure: 25 min drive to Maui Ocean Center, High Speed Internet Access, Wireless Internet This three bedroom, three bath...
3 Bedrooms, 3 Baths, Sleeps 6
  • Condo
  • Pool
  • Jacuzzi
  • Community Hot Tub
  • Garden View
  • Beach: 5 min walk to Wailea Beach just infront of property
  • Shopping: 1 min walk to Shops At Wailea
  • Sports: 5 min drive to Wailea Golf and Tennis
  • Adventure: 25 min drive to Maui Ocean Center
  • High Speed Internet Access
  • Wireless Internet
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
Rates
$1900 / night
Wailea rentals. 3 Bedrooms, 3 Baths, Sleeps 6, Villa, Community Pool, Jacuzzi, Community Hot Tub, Garden View, Beach: 5 min walk to Wailea Beach just infront of property, Shopping: 1 min walk to Shops At Wailea, Sports: 5 min drive to Wailea Golf and Tennis, Adventure: 25 min drive to Maui Ocean Center, High Speed Internet Access, Wireless Internet WBV Penthouse 105 is an artist...
3 Bedrooms, 3 Baths, Sleeps 6
  • Villa
  • Community Pool
  • Jacuzzi
  • Community Hot Tub
  • Garden View
  • Beach: 5 min walk to Wailea Beach just infront of property
  • Shopping: 1 min walk to Shops At Wailea
  • Sports: 5 min drive to Wailea Golf and Tennis
  • Adventure: 25 min drive to Maui Ocean Center
  • High Speed Internet Access
  • Wireless Internet
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
Rates
$1900 / night
Wailea rentals. 3 Bedrooms, 3 Baths, Sleeps 6, Villa, Community Pool, Jacuzzi, Community Hot Tub, Pool View, Garden View, Beach: 5 min walk to Wailea Beach, Shopping: 1 min walk to Shops At Wailea, Sports: 5 min drive to Wailea Golf and Tennis, Adventure: 25 min drive to Maui Ocean Center, High Speed Internet Access, Wireless Internet An international collection of...
3 Bedrooms, 3 Baths, Sleeps 6
  • Villa
  • Community Pool
  • Jacuzzi
  • Community Hot Tub
  • Pool View
  • Garden View
  • Beach: 5 min walk to Wailea Beach
  • Shopping: 1 min walk to Shops At Wailea
  • Sports: 5 min drive to Wailea Golf and Tennis
  • Adventure: 25 min drive to Maui Ocean Center
  • High Speed Internet Access
  • Wireless Internet
An international collection of art and artifacts are found throughout this luxuriously appointed 2600 square foot three bedroom, three bath penthouse. A tiki bar in the great room adds an extra... Read More
Rates
$1900 / night
Guest Rating:
Wailea luxury rentals 1 - 10 of 38   
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If you obtain a lower rate within 24 hours of paying for your booking, we will refund the difference!
The luxurious Wailea rental options that we've chosen are certain to fulfill your Hawaiian luxury fantasies. We can provide you with just about anything you're looking for, including:
  • Your own private garden complete with waterfalls and arcing bridges in and around your Hawaii luxury accommodations
  • Your own private waterfall equipped pool dividing your luxury Wailea vacation home from the Pacific ocean
  • Abundant home upgrades from marble and granite to the finest, most meticulous details in colors and textures
  • The calming sounds of the ocean right out the windows of your Hawaii luxury vacation accommodations


If you're looking to find the ultimate in luxury Wailea accommodations, allow us to show you how Hawaiian Beach Rentals can facilitate a vacation to remember. You can look through our detailed Wailea luxury accommodations listings and get an understanding of the different amenities and property features we can offer you. If you see something you like, you can telephone us at our toll-free number or click the "Contact Us" button to get to our contact request forms. We'll be happy to speak with you right away to begin turning your luxury Wailea vacation into a reality. Thanks for coming to HawaiianBeachRentals.com and please keep us in mind when it's time to find an unforgettable Hawaiian luxury vacation rental.
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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.
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