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Wailea Holiday Rentals

70 Wailea Holiday Rentals were found matching your criteria.


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

  38 reviews   Add to Favorites

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


Featured

$2303 - $4790 /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
$299 - $399 /night
$2093 - $4490 /week
Palms at Wailea #1105 Oceanview Completely Remodeled 2Bd ...

  31 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 !

  25 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


Special Offer
$695 - $1950 /night
Ho'olei Luxury Ocean View Villa across from Grand Wailea

Townhome: 3 Bedroom, 3.5 Bathroom, Sleeps 10
Location: Wailea, Hawaii, United States


$1450 - $1600 /night
One-of-a-kind Maui Getaway!

Home: 4 Bedroom, 3.5 Bathroom, Sleeps 10
Location: Wailea, Hawaii, United States


$750 - $2550 /night
Luxurious Oceanfront Villa

Villa: 4 Bedroom, 3 Bathroom, Sleeps 10
Location: Wailea, Hawaii, United States


$225 - $275 /night
$1575 - $2990 /week
Wailea Ekolu #407 Completely Remodeled with Panroamic Oce...

  9 reviews   Add to Favorites

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


$220 - $220 /night
$1435 - $1820 /week
Grand Champions #132 - Top Floor with Tennis Center and D...

  20 reviews   Add to Favorites

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


$149 - $269 /night
$1043 - $2890 /week
Palms at Wailea 609 Ground Level Garden View - 1Bd 2Ba Sl...

  10 reviews   Add to Favorites

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


$150 - $320 /night
$980 - $2415 /week
Fall Specials! Ocean View 2-BR Condo Overlooking Golf Course

  18 reviews   Add to Favorites

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


$189 - $289 /night
$1323 - $2990 /week
Wailea Ekolu #102 2 Bd 2 Bath, Ocean View, A/C, Sleeps 6 ...

  56 reviews   Add to Favorites

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


$169 - $254 /night
$1183 - $2990 /week
Palms at Wailea 702 Upstairs Garden View 1B/2B Sleeps 4. ...

  32 reviews   Add to Favorites

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


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

  39 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...

  22 reviews   Add to Favorites

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


$225 - $295 /night
$1575 - $3950 /week
Wailea Ekolu #406 2 Bd 2Ba Panoramic Ocean View, Full A/C...

  2 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 2303 Ground Floor 2bd 2ba Sleeps 6 Great ...

  30 reviews   Add to Favorites

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


$189 - $224 /night
$1323 - $2990 /week
Grand Champions #45 is a 2bd 2ba Ocean view condo that Sl...

  8 reviews   Add to Favorites

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


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

  28 reviews   Add to Favorites

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


$310 - $310 /night
$1995 - $2555 /week
Wailea Ekolu #908 - Top Floor Two BR with Big Ocean Views

  10 reviews   Add to Favorites

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


$185 - $185 /night
$1190 - $1680 /week
Grand Champions #121

  12 reviews   Add to Favorites

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


$325 - $325 /night
$2135 - $2695 /week
Wailea Ekolu #310 All New and Spectacular Ocean Views !!!

  14 reviews   Add to Favorites

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


$215 - $295 /night
$1505 - $3950 /week
Wailea Ekolu #1108 2 Bd. 2Ba. Premier Ocean View! Summer ...

  1 reviews   Add to Favorites

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


$215 - $315 /night
$1505 - $3950 /week
Wailea Ekolu #201 Remodeled 2Bd/2Ba Oceanview Condo Sleeps 6

  11 reviews   Add to Favorites

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


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