Wailea Vacation Rentals & Apartments - 330 Rentals Available
330 Vacation rentals
Wonderful Luxury Maui Condos
Wailea Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 2 minutes
$225.00
from $225.00 / night
Seaside Tropics Estate~Ocean views, private pool and hot tub
Wailea House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 8 8
- min stay varies
- Nearest beach 3 mi
- Swimming pool
- Child friendly
$2,163.00
from $2,163.00 / 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
Responds fast! Avg. 3 hours 9 minutes
$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
Fantastic Beach Front 2 Bedroom Condo MAKENA SURF RESORT, #B-205
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$762.00
from $762.00 / 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
Fantastic Location - Beautiful Oceanfront Condo -Makena Surf Resort # E-205
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$762.00
from $762.00 / night
Stunningly Remodeled Ocean View Unit -Wailea Ekahi #22D
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$335.00
from $335.00 / night
Remodeled Second Floor 2 BDRM Condo Wailea Elua Village # 202
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$479.00
from $479.00 / 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
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
$399.00
from $399.00 / night
Beautiful Remodeled Ground Floor Unit- Wailea Ekahi 4C
Wailea Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$265.00
from $265.00 / night
Beautiful Groundfloor Wailea Condo - Wailea Ekahi #24B
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$165.00
from $165.00 / 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
$690.00
from $690.00 / night
Beautiful Views and Location - Wailea Grand Champions #163
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$189.00
from $189.00 / night
Upgraded Condo- Beachfront- Easy Beach Access- MAKENA SURF RESORT, #B-204
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$762.00
from $762.00 / night
Beautiful Oceanfront Ground Floor Unit MAKENA SURF RESORT, #G-101
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$690.00
from $690.00 / night
Beautiful & Spacious Ocean View Condo WAILEA ELUA, #0902
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$399.00
from $399.00 / night
Stunning, Remodeled, 2 Bedroom WAILEA EKOLU, #914
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$302.00
from $302.00 / night
Gorgeous Ground Floor 1 Bedroom WAILEA ELUA, #2003
Wailea Apartment
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$409.00
from $409.00 / night
Beautifully Renovated 2 BDRM WAILEA ELUA, #2201
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$419.00
from $419.00 / night
Beautiful Views Await You Here - WAILEA ELUA, #1002
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$799.00
from $799.00 / 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
$629.00
from $629.00 / night
Beautiful Remodeled Beach Front 2 Bed. Unit-Royal Mauian #614
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$380.00
from $380.00 / night
Stunning Ground Floor 2 BDRM Condo WAILEA ELUA, #1403*
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$899.00
from $899.00 / night
Upgraded Unit w/ Beautiful Ocean Views -MAKENA SURF RESORT, #F-107
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$899.00
from $899.00 / night
Luxurious Oceanfront Corner Unit SURF RESORT, #F-212
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$690.00
from $690.00 / night
Stunning Golf & Ocean Views - Wailea Grand Champions #180
Wailea Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$229.00
from $229.00 / 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
$1,195.00
from $1,195.00 / night
Second Floor 2 BDRM w/ Sweeping Views WAILEA ELUA, #2010
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$419.00
from $419.00 / night
Stunning Golf & Ocean Views - Wailea Grand Champions #154
Wailea Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$299.00
from $299.00 / 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
Beautiful Ocean Views - Wailea Elua Village #802
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$389.00
from $389.00 / night
Prime Wailea 2 BDRM Condo Wailea Elua Village # 801
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$419.00
from $419.00 / 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
$419.00
from $419.00 / night
Lovely Ground Floor 2 BDRM Condo Wailea Elua Village # 105
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$419.00
from $419.00 / night
Fantastic Location - Beautiful Condo -Makena Surf Resorts # G-204
Wailea Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 5 nights min
- Swimming pool
- Child friendly
- Car not necessary
$690.00
from $690.00 / night
Private 4 Bed. Beach Front House on Charley Young's Beach - Indo Lotus Beach
Wailea Apartment
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 5 nights min
- Child friendly
- Car not necessary
- Air conditioning
$1,349.00
from $1,349.00 / 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
$1,796.00
from $1,796.00 / 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
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