Wailea Vacation Rentals & Apartments - 240 Rentals Available
240 Vacation rentals
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
$1,254.00
from $1,254.00 / night
Castaway Cove C201 at Wailea Beach Villas
Wailea House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,650.00
from $1,650.00 / night
Stunningly Remodeled Ocean View Unit -Wailea Ekahi #22D
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$389.00
from $389.00 / night
Remodeled Second Floor 2 BDRM Condo Wailea Elua Village # 202
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$729.00
from $729.00 / night
Gorgeous Remodeled Ocean Front Condo - Makena Surf Resort G-206
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$919.00
from $919.00 / night
Fantastic Location - Beautiful Oceanfront Condo -Makena Surf Resort # E-205
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$1,009.00
from $1,009.00 / night
Beautifully Renovated 2 BDRM WAILEA ELUA, #2201
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$729.00
from $729.00 / night
Remodeled Mountain View 2 BDRM Condo - Royal Mauian #601
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$220.00
from $220.00 / night
Stunning, Remodeled, 2 Bedroom WAILEA EKOLU, #914
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$379.00
from $379.00 / night
WAILEA ELUA, #0702
Wailea Apartment
- 2 bedrooms 2
- sleeps 6 6
- 5 nights min
- Ask about children
- Ask about pets
$410.00
from $410.00 / night
Upgraded Unit w/ Beautiful Ocean Views Makena Surf Resort # C-103
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$839.00
from $839.00 / night
Leaving Program
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$749.00
from $749.00 / night
Gorgeous Ground Floor 1 Bedroom WAILEA ELUA, #2003
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$599.00
from $599.00 / night
Stunning Ground Floor 2 BDRM Condo WAILEA ELUA, #1403*
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$1,139.00
from $1,139.00 / night
Second Floor 2 BDRM w/ Sweeping Views WAILEA ELUA, #2010
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$729.00
from $729.00 / night
Best Kihei Location; Oceanfront with Stunning Views; Spacious 2BR on the Beach!
Wailea Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$295.00
from $295.00 / night
Luxurious Oceanfront Corner Unit SURF RESORT, #F-212
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$919.00
from $919.00 / night
Beautiful Ocean Views - Wailea Elua Village #802
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$729.00
from $729.00 / night
Upgraded Unit w/ Beautiful Ocean Views -MAKENA SURF RESORT, #F-107
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$919.00
from $919.00 / night
Ground Floor 2 BDRM Condo Wailea Elua Village # 1503
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$729.00
from $729.00 / night
Aqua Lani J305 Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,895.00
from $1,895.00 / night
Lovely Ground Floor 2 BDRM Condo Wailea Elua Village # 105
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$729.00
from $729.00 / night
Stunning 1 Bedroom Wailea Condo Wailea Elua # 206
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$599.00
from $599.00 / night
Classy 2 BD Condo W/ Excellent Amenities Wailea Elua Village # 1204
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$1,009.00
from $1,009.00 / night
Fantastic Location - Beautiful Condo -Makena Surf Resorts # G-204
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$919.00
from $919.00 / 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
$239.00
from $239.00 / night
Prime Oceanfront 3Bd/3Ba Condo Wailea Elua #1305
Wailea Apartment
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$2,649.00
from $2,649.00 / 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
$4,900.00
from $4,900.00 / night
Sun Splash C301 Wailea Beach Villas
Wailea House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,950.00
from $2,950.00 / night
Exceptional Ocean View; Great Kihei Location; Walk To Beach & Restaurants!
Wailea Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 4 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$165.00
from $165.00 / 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
$2,450.00
from $2,450.00 / night
Gorgeous Beach Front Condo MAKENA SURF RESORT, #E-202
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$1,009.00
from $1,009.00 / night
Beautiful Beach Front 2 BDRM Condo - Makena Surf Resort # B-304
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$1,009.00
from $1,009.00 / night
Bali Hai Pool Villa F102 at Wailea Beach Villas
Wailea House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,550.00
from $1,550.00 / night
Remodeled 3BD w/AC - Great Location - Royal Mauian #302
Wailea Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$659.00
from $659.00 / night
Wailea Seashore Suite K507 at Wailea Beach Villas
Wailea House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,150.00
from $1,150.00 / night
Oceanfront Living 2 Bed 2 Bath Condo- MAKENA SURF RESORT, #E-104
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$899.00
from $899.00 / night
Wailea Sunset Estate
Wailea House
- 5 bedrooms 5
- 6 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$4,950.00
from $4,950.00 / night
Beautiful Golf & Ocean Views - WAILEA GRAND CHAMPION #148
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$259.00
from $259.00 / night
Grand Seascape K407 Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,595.00
from $1,595.00 / night
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