Wailea Vacation Rentals & Apartments with Swimming Pool - 68 Rentals Available.
68 Vacation rentals
Filters applied: Swimming pool
Aloha Kai Suite at Wailea Beach Villas PH 205
Wailea Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$895
from $895 / night
MAKENA SURF RESORT, #G-201*
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$540
from $540 / night
MAKENA SURF RESORT, #E-202
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$599
from $599 / night
MAKENA SURF RESORT, #C-103
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$446
from $446 / night
Sweeping Ocean Views; Private High End Condo!
Wailea Condo
- 1 bedroom 1
- 2 bathrooms
- Sleeps 4 4
- 4 nights min
- Swimming pool
- Air conditioning
$199
from $199 / night
MAKENA SURF RESORT, #B-205^
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$612
from $612 / night
Ho'olei #93-5
Wailea Apartment
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$810
from $810 / night
MAKENA SURF RESORT, #E-104^
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$599
from $599 / night
MAKENA SURF RESORT, #B-304^
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$579
from $579 / night
Wailea Ekolu #1106
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$315
from $315 / night
Wailea Ekahi #4E
Wailea Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$230
from $230 / night
MAKENA SURF RESORT, #G-101
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$540
from $540 / night
WAILEA EKOLU, #914
Wailea Apartment
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 5 5
- Min stay varies
- Swimming pool
- Ask about children
$267
from $267 / night
Grand Champions # 8
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$225
from $225 / night
Wailea Ekahi #41B
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$265
from $265 / night
MAKENA SURF RESORT, #G-204*^
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$540
from $540 / night
Grand Champions # 163
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$235
from $235 / night
Wailea Ekahi #17B
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$220
from $220 / night
Wailea Elua #2011
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$385
from $385 / night
Palms at Wailea #1606
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
$220
from $220 / night
MAKENA SURF RESORT, #B-101^
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$700
from $700 / night
Grand Champions # 35
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$235
from $235 / night
WAILEA EKOLU, #401*
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
$250
from $250 / night
Grand Champions # 150
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$270
from $270 / night
MAKENA SURF RESORT, #E-206^
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$612
from $612 / night
MAKENA SURF RESORT, #E-204^
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$612
from $612 / night
MAKENA SURF RESORT, #F-212
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$540
from $540 / night
MAKENA SURF RESORT, #G-104
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$540
from $540 / night
MAKENA SURF RESORT, #E-205
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$612
from $612 / night
Wailea Ekahi #17E
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$325
from $325 / night
Wailea Ekahi #14D
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$370
from $370 / night
MAKENA SURF RESORT, #B-102^
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$473
from $473 / night
Grand Champions # 186
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$235
from $235 / night
MAKENA SURF RESORT, #B-207
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$680
from $680 / night
Grand Champions # 139
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$260
from $260 / night
Grand Champions # 122
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$200
from $200 / night
Grand Champions # 86
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$210
from $210 / night
Wailea Ekahi #53C
Wailea Apartment
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$435
from $435 / night
Wailea Ekahi #17D
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$325
from $325 / night
WAILEA GRAND CHAMPION, #180^
Wailea Apartment
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
$250
from $250 / night
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