Wailea Vacation Rentals & Apartments with Swimming Pool - 324 Rentals Available.
324 Vacation rentals
Filters applied: Swimming pool
Wonderful Luxury Maui Condos
Wailea Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$185.00
from $185.00 / 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
Responds fast! Avg. 3 hours 5 minutes
$159.00
from $159.00 / night
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
$995.00
from $995.00 / night
Wailea Elua Village #4C
Wailea Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$235.00
from $235.00 / night
Royal Ilima A201 Wailea Beach Villas
Wailea House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,800.00
from $2,800.00 / night
Grand Champions # 180
Wailea Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$251.00
from $251.00 / night
Wailea Elua Village # 2107
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$409.00
from $409.00 / night
Wailea Elua #2204
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$529.00
from $529.00 / night
WAILEA EKAHI, #24B^
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$165.00
from $165.00 / night
MAKENA SURF RESORT, #F-212
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$539.00
from $539.00 / night
Wailea Elua Village # 801
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$409.00
from $409.00 / night
Front Row Ocean View property- WAILEA GRAND CHAMPION, #154
Wailea Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$265.00
from $265.00 / night
WAILEA EKOLU, #914
Wailea Apartment
- 2 bedrooms 2
- sleeps 5 5
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$292.00
from $292.00 / night
WAILEA GRAND CHAMPION, #163
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$201.00
from $201.00 / night
Wailea Elua Village # 1503
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$409.00
from $409.00 / night
WAILEA ELUA, #0902
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$441.00
from $441.00 / night
Coral Gardens at Makena Bay
Wailea House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,700.00
from $2,700.00 / night
Wailea Elua Village # 1204
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$599.00
from $599.00 / night
Grand Seascape K407 Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$850.00
from $850.00 / night
Makena Surf Resort # E-205
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$612.00
from $612.00 / night
Castaway Cove C201 at Wailea Beach Villas
Wailea House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$995.00
from $995.00 / night
Wailea Elua #1305
Wailea Apartment
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$1,569.00
from $1,569.00 / night
Wailea Elua #2003
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$399.00
from $399.00 / night
Aqua Lani J305 Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$945.00
from $945.00 / night
Makena Surf Resort # E-204
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$619.00
from $619.00 / night
Wailea Elua # 206
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$399.00
from $399.00 / night
MAKENA SURF RESORT, #B-205
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$599.00
from $599.00 / night
WAILEA ELUA, #1403*
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$699.00
from $699.00 / night
MAKENA SURF RESORT, #E-104
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$619.00
from $619.00 / night
Makena Surf # B-207
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$750.00
from $750.00 / 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
$209.00
from $209.00 / night
Makena Surf Resorts # G-204
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$590.00
from $590.00 / night
MAKENA SURF RESORT, #G-101
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$590.00
from $590.00 / night
Golden Mandarin D102 Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,495.00
from $1,495.00 / night
MAKENA SURF RESORT, #G-206^
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$539.00
from $539.00 / night
WAILEA ELUA, #1002
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$699.00
from $699.00 / night
WAILEA ELUA, #2010
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$409.00
from $409.00 / night
Exceptional Ocean View; Great Kihei Location; Walk To Beach & Restaurants!
Wailea Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 4 nights min
- Swimming pool
- Child friendly
- Air conditioning
$145.00
from $145.00 / night
Wailea Elua Village # 105
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$409.00
from $409.00 / night
Wailea Ekolu # 312
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$189.00
from $189.00 / night
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