More Filters

Price per Night Range

$0
$1000+


Accommodations


Interest


Wailea Vacation Rentals

66 Wailea Vacation Rentals were found matching your criteria.


Featured

$2163 - $4590 /week
Palms at Wailea #1508 Panroamic Ocean Views 2/2 Sleeps 6 ...

  34 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States


Featured
$250 - $250 /night
$1575 - $2135 /week
Grand Champions #163 2Br/2Ba Convenient 1st Floor Location.

  35 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States


Featured
$266 - $370 /night
$1862 - $2590 /week
Wailea Ekahi 46F- Spacious 2 bedroom 2 Bath Condo in Wailea!

  5 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States


Featured
$299 - $399 /night
$2093 - $4490 /week
Palms at Wailea #1105 Oceanview Completely Remodeled 2Bd ...

  26 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States


Featured
$285 - $285 /night
$1750 - $2380 /week
Grand Champion #139 - Beautiful Full Renovation 2015 !

  24 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States


$199 - $289 /night
$1393 - $3490 /week
Wailea Ekolu 805 Deluxe 2 Bd. 2 Bath, Ocean View Townhouse!

  23 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States


$189 - $224 /night
$1323 - $2990 /week
Grand Champions #48 is a 2bd 2ba Ocean View condo that Sl...

  58 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States


$179 - $224 /night
$1253 - $2990 /week
Wailea Grand Champions #50 is a 2 Bd 2 Ba Upgraded Unit. ...

  13 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States


$249 - $349 /night
$1743 - $3990 /week
Palms at Wailea #1101 Great Ocean Views! Large Sun Deck! ...

  45 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States


$195 - $330 /night
$1225 - $2625 /week
Summer Specials! Spacious Renovated 2-BR Condo with Centr...

  30 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States


$310 - $310 /night
$1995 - $2555 /week
Wailea Ekolu #1206 - Modern, Luxurious 2 BR 2 BA Condominium

  5 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States


$199 - $299 /night
$1393 - $3240 /week
Palms at Wailea #1204 Ocean View, Sleeps 4.

  27 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States


$245 - $285 /night
$1540 - $1995 /week
Palms at Wailea #1606 Spacious 2Br/2Ba - Great Rates - Fr...

  50 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States



$5670 - $11165 /week
Ho'olei #39-3 'Ocean's Invitation' Premier Location and V...

  18 reviews   Add to Favorites

Condo: 3 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Wailea, Hawaii, United States


$325 - $325 /night
$2135 - $3570 /week
Wailea Ekolu #1610

  5 reviews   Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 5
Location: Wailea, Hawaii, United States


$174 - $224 /night
$1218 - $2990 /week
Grand Champions #51 is a 2Bd 2Ba is a large condo that sl...

  36 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States


$210 - $210 /night
$1365 - $1820 /week
Grand Champions #132 - Top Floor with Tennis Center and D...

  18 reviews   Add to Favorites

Condo: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Wailea, Hawaii, United States


$449 - $499 /night
$3143 - $5750 /week
Wailea Elua #2108 Gorgeous Unit - Ocean View

  21 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 7
Location: Wailea, Hawaii, United States


$304 - $404 /night
$2128 - $4540 /week
Stop! Look No Further! Palms at Wailea #1503 Ocean View B...

  14 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States



$4970 - $10465 /week
Ho'olei #55-2 Luxurious and Spacious Wailea Rental Home

  9 reviews   Add to Favorites

Condo: 3 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Wailea, Hawaii, United States


$440 - $520 /night
$3080 - $3640 /week
Grand Champions #033

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States


$115 - $220 /night
$700 - $1645 /week
Beautifully Renovated 1-BR Condo, Nearby World-Class Golf...

  10 reviews   Add to Favorites

Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States


$440 - $535 /night
$3080 - $3745 /week
Grand Champions #090

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States


$179 - $299 /night
$1253 - $3240 /week
Palms at Wailea 603 2bd 2ba Sleeps 6 Great Rates!!

  15 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States


$169 - $269 /night
$1183 - $2990 /week
Palms at Wailea Unit #2305 Quiet and Very Private! Summer...

  20 reviews   Add to Favorites

Condo: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Wailea, Hawaii, United States


This map is intended to be used as a reference only.

Maui Top Cities

Vacation Rental Deals and Specials

Find additional Vacation Rentals: