Wailea Vacation Rentals & Apartments - 495 Rentals Available
495 Vacation rentals
Wonderful Luxury Maui Condos
Wailea Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 8 minutes
$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
MAKENA SURF RESORT, #B-205
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$763.00
from $763.00 / night
Wailea Sunset Bungalow
Wailea House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,095.00
from $1,095.00 / 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
$1,195.00
from $1,195.00 / 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
Wailea Elua Village # 202
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$440.00
from $440.00 / 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
MAKENA SURF RESORT, #G-206^
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 Village # 2107
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$425.00
from $425.00 / night
WAILEA GRAND CHAMPION, #163
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$200.00
from $200.00 / night
Wailea Ekahi #22D
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$299.00
from $299.00 / night
WAILEA ELUA, #0702
Wailea Apartment
- 2 bedrooms 2
- sleeps 6 6
- 5 nights min
- Ask about children
- Ask about pets
$409.00
from $409.00 / night
Wailea Elua #1601
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$420.00
from $420.00 / night
WAILEA ELUA, #2201
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$349.00
from $349.00 / night
Property Title
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$763.00
from $763.00 / 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
WAILEA EKOLU, #914
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$292.00
from $292.00 / 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
Hale Makena Maui
Wailea Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Ask about pets
Responds fast! Avg. 1 hour 27 minutes
$2,700.00
from $2,700.00 / night
WAILEA ELUA, #0902
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$440.00
from $440.00 / night
Makena Surf Resort # C-103
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$495.00
from $495.00 / night
WAILEA ELUA, #1002
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$700.00
from $700.00 / 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
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
MAKENA SURF RESORT, #F-107
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$899.00
from $899.00 / night
Grand Champions # 180
Wailea Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$250.00
from $250.00 / night
Best Kihei Location; Oceanfront with Stunning Views; Spacious 2BR on the Beach!
Wailea Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
- Private garden
$295.00
from $295.00 / 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
MAKENA SURF RESORT, #F-212
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$590.00
from $590.00 / night
ROYAL MAUIAN, #614
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$379.00
from $379.00 / night
WAILEA ELUA, #1403*
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$700.00
from $700.00 / 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
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 # 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
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 ELUA, #2010
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ski
- Child friendly
$379.00
from $379.00 / 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
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
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