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Wailea Vacation Rentals

67 Wailea Vacation Rentals were found matching your criteria.


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1 Bedroom Ocean View/ Golf Front

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


$250 - $250 /night
$1575 - $2135 /week
Grand Champions #49 - Ground Floor, Corner Location with ...

  5 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
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


$225 - $275 /night
$1575 - $2890 /week
Palms at Wailea #2108 Gorgeous Unit 1Bd 2 Ba Great Rates!

  12 reviews   Add to Favorites

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


$270 - $270 /night
$1785 - $2485 /week
Wailea Ekolu #1604 - Beautiful Upgrades and Full Remodel

  18 reviews   Add to Favorites

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


$279 - $399 /night
$1953 - $4490 /week
Palms at Wailea #205 2B/2B - Luxurious! - Jan-Feb. Specia...

  12 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


$150 - $320 /night
$980 - $2450 /week
Beautiful 2-Bedroom Condo with a Partial Ocean View

  53 reviews   Add to Favorites

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


$159 - $184 /night
$1113 - $2490 /week
Grand Champions #151 is a1 Bd 2 Ba fronting the Wailea Go...

  1 reviews   Add to Favorites

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


$299 - $299 /night
$2093 - $6050 /week
Grand Champions #143 is a 3 BR 2 bath renovated Summer Sp...

  5 reviews   Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Wailea, Hawaii, United States


$185 - $185 /night
$1190 - $1855 /week
Grand Champions #162 - Top Floor with Great Ocean View !

  16 reviews   Add to Favorites

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


$190 - $250 /night
$1330 - $1750 /week
Wailea Ekahi 48C ~ 1 BR 2 Bath Wailea Condo! Book it now!

  8 reviews   Add to Favorites

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


$345 - $425 /night
$2415 - $5250 /week
Wailea Elua #2110 - Gorgeous Ocean View 2B/2B

  29 reviews   Add to Favorites

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


$150 - $320 /night
$980 - $2415 /week
Spring Specials! Ocean View 2-BR Condo Overlooking Golf C...

  17 reviews   Add to Favorites

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


$250 - $250 /night
$1575 - $2135 /week
Grand Champions #186 2Br/2Ba Near The Pool, Great Locatio...

  8 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


Contact Owner
Directly For Rates
2 Bedroom Garden View

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



$4970 - $10465 /week
Ho'olei #t6 - Biggest Floor Plan. Close to Wailea Beach -...

  13 reviews   Add to Favorites

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


$180 - $335 /night
$1190 - $2800 /week
Spring Specials! Stunning 3-BR Condo on a World-Class Gol...

  26 reviews   Add to Favorites

Condo: 3 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


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

  2 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
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


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

  7 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 #1501 Ocean View Inner Court Ground Floor...

  35 reviews   Add to Favorites

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


$169 - $224 /night
$1203 - $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


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