Are you looking for the best online source for Wailea vacation rentals? If so, you've come to the right place! Here at Hawaiian Beach Rentals, we pride ourselves in offering a wide array of Wailea vacation rentals to match your unique needs. Also consider our 72 Wailea condos and 78 Wailea hotels.
Wailea vacation rentals 1 - 10 of 38   
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Wailea rentals. 3 Bedrooms, 3 Baths, 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, 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
$1788 to $2750 / night
Special Rate
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
$1235 to $2400 / night
Special Rate
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
$1430 to $2200 / night
Special Rate
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
$1235 to $1900 / night
Special Rate
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
$1235 to $1900 / night
Special Rate
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
$1235 to $1900 / night
Special Rate
Wailea rentals. 3 Bedrooms, 3 Baths, Sleeps 6, Villa, Community Pool, 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
  • 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 luxuriously furnished wraparound lanai that features over 900 square feet of flexible entertaining space. The spacious master bedroom also offers a partial... Read More
Rates
$1235 to $1900 / night
Special Rate
Wailea rentals. 2 Bedrooms, 2 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 The master bed is a four poste...
2 Bedrooms, 2 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
The master bed is a four poster king and there are twin beds in the second bedroom that can be pushed together to make in to a king-size bed. There is also a pull out queen size sofa bed in the... Read More
Rates
$1073 to $1650 / night
Special Rate
Wailea rentals. 2 Bedrooms, 2 Baths, Sleeps 6, Villa, Community Pool, Jacuzzi, Community Hot Tub, Ocean View, Beach: 5 min walk to 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 Located on the top floor, this...
2 Bedrooms, 2 Baths, Sleeps 6
  • Villa
  • Community Pool
  • Jacuzzi
  • Community Hot Tub
  • Ocean View
  • Beach: 5 min walk to 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
Located on the top floor, this 2 bedroom, 2 bath penthouse features amazing views from the spacious lanai. Two twin beds and an additional pull out sofa bed make it a perfect fit for families. This... Read More
Rates
$1073 to $1650 / night
Special Rate
Wailea rentals. 2 Bedrooms, 2 Baths, Sleeps 6, Villa, Community Pool, Community Hot Tub, Garden View, Beach: 5 min walk to Wailea Beach in front 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, Wireless Internet This two bedroom, two bath Pen...
2 Bedrooms, 2 Baths, Sleeps 6
  • Villa
  • Community Pool
  • Community Hot Tub
  • Garden View
  • Beach: 5 min walk to Wailea Beach in front 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
  • Wireless Internet
This two bedroom, two bath Penthouse unit is beautifully furnished and offers a well appointed lanai. The proximity to the pool is very convenient and the extra spacious living area and pull-out... Read More
Wailea vacation 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!
Be it a private oceanfront cottage or a luxury home fit for the stars, let us help you discover the Wailea vacation rental of your dreams. We recognize that planning your Hawaiian holiday is crucial to getting the most out of your vacation time, and we can take the hassles out of the preparation. Accordingly, our customers are guaranteed the service that only a highly qualified local Hawaiian vacation professional can offer. Our local and knowledgeable staff can help unlock the secrets of Wailea to make the most of your valuable vacation. Hawaiian Beach Rentals is here for you whether you need to locate the perfect romantic table at a beachfront restaurant or give windsurfing a try for the first time.

We hope you find just what you're looking for as you view the various Wailea vacation rentals on our site, and we look forward to talking with you when you do. If you discover a Wailea vacation rental property that catches your eye, just complete one of our easy contact forms and we'll provide you with more information. If you prefer, you can also call us anytime between 8:00am and 11:00pm Eastern time to discuss your Hawaiian vacation needs. We're here to help you plan the Wailea vacation of your dreams! Thank you for stopping by - our wish is that you discover the perfect Wailea vacation rental for your ideal Hawaiian vacation!
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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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