Wailea Vacation Rentals & Apartments with Swimming Pool - 277 Rentals Available.
277 Vacation rentals
Filters applied: Swimming pool
Wonderful Luxury Maui Condos
Wailea Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
$299.00
from $299.00 / night
South Kihei Paradise & Great Location
Wailea Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$204.00
from $204.00 / 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
$1,140.00
from $1,140.00 / 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
$1,295.00
from $1,295.00 / 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
$309.00
from $309.00 / 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
$503.00
from $503.00 / 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
$639.00
from $639.00 / 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
$649.00
from $649.00 / 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
$413.00
from $413.00 / night
Remodeled Elegance & Luxury - Daily Housekeeping Elua Village # 2107
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$382.00
from $382.00 / 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
$180.00
from $180.00 / 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
$302.00
from $302.00 / night
Beautiful Oceanfront Ground Floor Unit MAKENA SURF RESORT, #G-101
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$639.00
from $639.00 / night
Beautiful Views and Location - Wailea Grand Champions #163
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$210.00
from $210.00 / night
Upgraded Condo- Beachfront- Easy Beach Access- MAKENA SURF RESORT, #B-204
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$747.00
from $747.00 / night
Upgraded Unit w/ Beautiful Ocean Views Makena Surf Resort # C-103
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$611.00
from $611.00 / night
Beautiful & Spacious Ocean View Condo WAILEA ELUA, #0902
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$503.00
from $503.00 / 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
$419.00
from $419.00 / night
Stunning Golf & Ocean Views - Wailea Grand Champions #180
Wailea Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$275.00
from $275.00 / 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
$746.00
from $746.00 / night
Prime Wailea 2 BDRM Condo Wailea Elua Village # 801
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$413.00
from $413.00 / 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
$413.00
from $413.00 / 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
$674.00
from $674.00 / 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
$413.00
from $413.00 / 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
$899.00
from $899.00 / night
Ground Floor 2 BDRM Condo Wailea Elua Village # 1503
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$413.00
from $413.00 / 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
$1,195.00
from $1,195.00 / 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
$413.00
from $413.00 / 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
$419.00
from $419.00 / 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
$746.00
from $746.00 / 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
$639.00
from $639.00 / 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
$229.00
from $229.00 / night
Prime Oceanfront 3Bd/3Ba Condo Wailea Elua #1305
Wailea Apartment
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$1,422.00
from $1,422.00 / 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
$2,900.00
from $2,900.00 / night
Sun Splash C301 Wailea Beach Villas
Wailea House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,576.00
from $1,576.00 / 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
Royal Ilima A201 Wailea Beach Villas
Wailea House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$2,850.00
from $2,850.00 / night
Stunning Ground Floor 2 Bedroom Wailea Elua #307
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$413.00
from $413.00 / night
Gorgeous Beach Front Condo MAKENA SURF RESORT, #E-202
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$680.00
from $680.00 / night
Beautiful Beach Front 2 BDRM Condo - Makena Surf Resort # B-304
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$649.00
from $649.00 / night
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