Wailea Vacation Rentals & Apartments with Swimming Pool - 198 Rentals Available.
198 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
- 5 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$895.00
from $895.00 / night
South Kihei Paradise & Great Location
Wailea Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$159.00
from $159.00 / night
WAILEA GRAND CHAMPION, #180^
Wailea Apartment
- 3 bedrooms 3
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$250.00
from $250.00 / night
MAKENA SURF RESORT, #E-206^
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$662.00
from $662.00 / night
MAKENA SURF RESORT, #G-101
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$529.00
from $529.00 / night
MAKENA SURF RESORT, #B-207
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$675.00
from $675.00 / night
WAILEA GRAND CHAMPION, #163
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$200.00
from $200.00 / night
MAKENA SURF RESORT, #F-212
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$486.00
from $486.00 / night
MAKENA SURF RESORT, #F-202
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$486.00
from $486.00 / night
WAILEA EKOLU, #914
Wailea Apartment
- 2 bedrooms 2
- Sleeps 5 5
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$292.00
from $292.00 / night
MAKENA SURF RESORT, #E-104^
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$559.00
from $559.00 / night
MAKENA SURF RESORT, #G-201*
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$529.00
from $529.00 / night
MAKENA SURF RESORT, #E-204^
Wailea Apartment
- 2 bedrooms 2
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$649.00
from $649.00 / night
WAILEA EKOLU, #401*
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$199.00
from $199.00 / night
MAKENA SURF RESORT, #E-202
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$589.00
from $589.00 / night
Sweeping Ocean Views; Private High End Condo!
Wailea Condo
- 1 bedroom 1
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Air conditioning
$199.00
from $199.00 / night
MAKENA SURF RESORT, #B-205^
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$662.00
from $662.00 / night
MAKENA SURF RESORT, #B-304^
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$662.00
from $662.00 / night
MAKENA SURF RESORT, #G-206^
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$539.00
from $539.00 / night
MAKENA SURF RESORT, #G-204*^
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$589.00
from $589.00 / night
MAKENA SURF RESORT, #G-104
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$590.00
from $590.00 / night
MAKENA SURF RESORT, #C-103
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$497.00
from $497.00 / night
MAKENA SURF RESORT, #B-101^
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$775.00
from $775.00 / night
WAILEA EKOLU, #312
Wailea Apartment
- 1 bedroom 1
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$189.00
from $189.00 / night
ROYAL MAUIAN, #302
Wailea Apartment
- 3 bedrooms 3
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$525.00
from $525.00 / night
MAKENA SURF RESORT, #E-205
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$649.00
from $649.00 / night
MAKENA SURF RESORT, #B-204
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$662.00
from $662.00 / night
WAILEA GRAND CHAMPION, #154
Wailea Apartment
- 3 bedrooms 3
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$265.00
from $265.00 / night
ROYAL MAUIAN, #614
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$379.00
from $379.00 / night
MAKENA SURF RESORT, #G-304
Wailea Apartment
- 3 bedrooms 3
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$775.00
from $775.00 / night
MAKENA SURF RESORT, #F-107*
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$809.00
from $809.00 / night
MAKENA SURF RESORT, #B-203^
Wailea Apartment
- 2 bedrooms 2
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$662.00
from $662.00 / night
MAKENA SURF RESORT, #C-102
Wailea Apartment
- 2 bedrooms 2
- Sleeps 5 5
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$497.00
from $497.00 / night
Loa's Lani
Wailea Villa
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- 3 nights min
- Swimming pool
- Air conditioning
$2,599.00
from $2,599.00 / night
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