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Vacation Rentals in Wailea, Maui

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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227 Trusted Wailea Rentals
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Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
20.0% off your stay
from
$208
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 4
Save
You added Polo Beach 1or 2 Bdrm Oceanfront Penthouse Condo to your Saves list
from
$599
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
20.0% off your stay
from
$208
Per Night
Also consider
Modern, Renovated & Relaxing 2 Bedroom 2 Bathroom
$160 - $250 / night
2 Bedrooms, sleeps 4
2 Bathrooms
Beachfront Wailea Beauty at NEW LOWEST  PRICES!!!
$170 - $250 / night
1 Bedroom, sleeps 4
2 Bathrooms
Ocean View, Remodeled, Stuff for the Kids, CLEAN
$250 - $325 / night
2 Bedrooms, sleeps 6
2 Bathrooms
Beautiful 1 bedroom - 6/2 - 15 and 6/22 - 7/6
$113 - $170 / night
1 Bedroom, sleeps 2
1 Bathroom
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added $179 PEACEFUL GRAND CHAMPION For 6- Upscale WAILEA to your Saves list
from
$189
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
$55 off per night
from
$255
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 4
Save
You added Aloha! Luxurious Palms at Wailea #703 2 bed 2 bath to your Saves list
from
$250
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Ekahi-2A Lower Village, Ocean Views and Sunsets to your Saves list
from
$410
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
Save
You added Beautiful Maui Wailea condo in beachfront building to your Saves list
from
$290
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
Save
You added Palms at Wailea 1 Bd 2 Ba Ocean View Ground Floor Sleeps 4 , Great Rates!!! to your Saves list
from
$179
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added WOW ! WHAT A GREAT VIEW ! 6th Night Free Til 9/30 to your Saves list
from
$395
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
from
$194
Per Night
Hawaii, Maui, Wailea Vacation Rentals
3 Bedrooms, 4 Bathrooms, Sleeps 8
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You added Ho'olei with Grand Wailea Resort Access & Views to your Saves list
from
$1,295
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 4
Save
You added Wailea Ekahi 11f: Ocean View/Renovated 2 BR Condo to your Saves list
from
$450
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
from
$370
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 4
Save
You added Wailea - Beachfront Luxury Polo Beach Club #408 to your Saves list
from
$595
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Amazing Wailea Surf Villa at Wailea Beach Villas to your Saves list
from
$645
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 5
Save
You added Elua Village # 701 - Luxury 2b/2b with Ocean View! to your Saves list
from
$395
Per Night
Hawaii, Maui, Wailea Vacation Rentals
3 Bedrooms, 4 Bathrooms, Sleeps 8
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You added Hoku at Ho'olei - Grand Wailea Resort Privileges to your Saves list
from
$1,095
Per Night
Hawaii, Maui, Wailea Vacation Rentals
3 Bedrooms, 2 Bathrooms, Sleeps 5
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You added Wailea Beach Villa ~ Top Floor Luxury ~ Best View to your Saves list
from
$875
Per Night
Hawaii, Maui, Wailea Vacation Rentals
Studio, 1 Bathroom, Sleeps 2
from
$230
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
from
$225
Per Night
Hawaii, Maui, Wailea Vacation Rentals
3 Bedrooms, 3 Bathrooms, Sleeps 8
Save
You added Wailea Orchid Villa - Panoramic Views! 3 Bd/3 Ba to your Saves list
from
$995
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
from
$220
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
Save
You added Wailea Ekolu - 180 Degree Ocean View from Every Rm to your Saves list
from
$265
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 4
from
$255
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
Save
You added Premier Wailea Ekahi 11E Ocean Front S. Maui Condo to your Saves list
from
$310
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Awesome!, Ocean Views, Great for Families/Couples to your Saves list
from
$235
Per Night
Hawaii, Maui, Wailea Vacation Rentals
3 Bedrooms, 2 Bathrooms, Sleeps 6
from
$365
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Summer Special-Book 6 Nights, Get the 7th Free to your Saves list
from
$230
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
Save
You added Palms at Wailea #1209 1 Bedroom 2 Bath Sleeps 4. Great Rates! to your Saves list
from
$199
Per Night
Hawaii, Maui, Wailea Vacation Rentals
3 Bedrooms, 3 Bathrooms, Sleeps 8
Save
You added Aloha Kai Suite at Wailea Beach Villas PH 205 to your Saves list
from
$895
Per Night
Hawaii, Maui, Wailea Vacation Rentals
3 Bedrooms, 4 Bathrooms, Sleeps 8
Save
You added Perfect Escape! Ho'Olei Dream -Super Close to Pool to your Saves list
from
$800
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Ekahi 20A Ground Floor Ocean view Lower Village to your Saves list
Free gift worth $220
from
$410
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 5
Save
You added $200/nt 7/24-31 - Wailea Ekahi 33A Lux Beach Resort to your Saves list
from
$250
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
Save
You added Luxurious Grand Champions #162 -- Ocean View! to your Saves list
from
$150
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 6
Save
You added Palms 1510. April & May SPECIALS, FreeSummerNights to your Saves list
from
$375
Per Night
Hawaii, Maui, Wailea Vacation Rentals
2 Bedrooms, 2 Bathrooms, Sleeps 4
from
$255
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 1 Bathroom, Sleeps 4
Save
You added Beautiful Wailea Gem! Remodeled! Affordable! to your Saves list
from
$140
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 3
Save
You added Wailea Ekahi 7G Luxury Ocean Front S Maui Condo to your Saves list
15.0% off your stay
from
$335
Per Night
Hawaii, Maui, Wailea Vacation Rentals
1 Bedroom, 2 Bathrooms, Sleeps 4
Save
You added EKAHI,37B,New Remodel, Ocean+Mountain View,Sleeps4 to your Saves list
from
$183
Per Night
Wailea Vacation Rentals

Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.

A Wailea Vacation

No matter how you like to relax, there is sure to be a great place to do it in Wailea. From an indulgent day at the Spa Grande to tee time at Wailea Old Blue Course, it is full of ways to treat yourself and have a great time. If you're feeling adventurous, Hawaiian Sailing Canoe Adventures allows small groups to enjoy sailing in an outrigger canoe, or if you just want to relax on the beach, Keawakapu is a perfect choice for everything from sunning to snorkeling. Whatever the day's adventures bring, choosing a vacation rental to stay in means you can go back to the privacy and comfort of your very own rental home away from home for a truly authentic experience.

Family-Friendly Wailea

From exploring the beaches to catching a dinner show at Honua'ula Luau, there are a variety of great experiences for children when vacationing to Wailea. With vacation rentals, you can rent a property to accommodate nearly any size family, and it is a fantastic excuse to bring everyone along. Without having to pay for extra hotel rooms, it can also be a great money saver when traveling with a large group. Enjoying a Wailea vacation with the entire family at your very own rental home will be sure to create wonderful memories for years to come.

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