Wailea Vacation Rentals & Apartments with Swimming Pool - 238 Rentals Available.
238 Vacation rentals
Filters applied: Swimming pool
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
$896.00
from $896.00 / 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
MAKENA SURF RESORT, #B-205^
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$662.00
from $662.00 / 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
Sea Breeze Suite J405 at Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$995.00
from $995.00 / 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
$199.00
from $199.00 / 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
$1,595.00
from $1,595.00 / night
Wailea Sunset Bungalow
Wailea House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,095.00
from $1,095.00 / night
MAKENA SURF RESORT, #B-101^
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$775.00
from $775.00 / night
Mer Et Soleil K408 Wailea Beach Villas
Wailea Villa
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,695.00
from $1,695.00 / 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
$2,701.00
from $2,701.00 / night
Golden Mandarin D102 Wailea Beach Villas
Wailea Villa
- 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
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
$2,600.00
from $2,600.00 / night
MAKENA SURF RESORT, #G-101
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$529.00
from $529.00 / night
Sandcastles Suite L509 Wailea Beach Villas
Wailea House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,650.00
from $1,650.00 / night
Wailea Seashore Suite K507 at Wailea Beach Villas
Wailea House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$995.00
from $995.00 / night
WAILEA EKOLU, #312
Wailea Apartment
- 1 bedroom 1
- sleeps 2 2
- min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$149.00
from $149.00 / night
WAILEA EKOLU, #914
Wailea Apartment
- 2 bedrooms 2
- sleeps 5 5
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$292.00
from $292.00 / night
Regal Mandalay M511 Wailea Beach Villas
Wailea House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 6 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,045.00
from $1,045.00 / night
MAKENA SURF RESORT, #E-204^
Wailea Apartment
- 2 bedrooms 2
- sleeps 6 6
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$599.00
from $599.00 / night
Orient Pacific Suite J505 at Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,025.00
from $1,025.00 / 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
$965.00
from $965.00 / night
Azure Azul M212 at Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$995.00
from $995.00 / night
MAKENA SURF RESORT, #G-204*^
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$590.00
from $590.00 / night
Sandy Surf K508 at Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,395.00
from $1,395.00 / night
MAKENA SURF RESORT, #F-202
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$486.00
from $486.00 / night
Sunny Surf E301 at Makena Surf
Wailea Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$995.00
from $995.00 / night
MAKENA SURF RESORT, #E-206^
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$662.00
from $662.00 / 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
$1,045.00
from $1,045.00 / night
MAKENA SURF RESORT, #C-103
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$496.00
from $496.00 / night
Bella Luna D302 Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$2,195.00
from $2,195.00 / night
MAKENA SURF RESORT, #E-205
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$599.00
from $599.00 / night
WAILEA GRAND CHAMPION, #163
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$189.00
from $189.00 / night
Floral Gardens Villa G102 Wailea Beach Villas
Wailea Villa
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,545.00
from $1,545.00 / night
Turquoise Cove G301 at Makena Surf
Wailea House
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- 6 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,295.00
from $1,295.00 / 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
$925.00
from $925.00 / night
Blue Horizons K308 Wailea Beach Villas
Wailea Villa
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,495.00
from $1,495.00 / night
MAKENA SURF RESORT, #E-202
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$599.00
from $599.00 / night
Wailea Sunset Estate
Wailea House
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- 6 nights min
- Swimming pool
- Child friendly
- Air conditioning
$2,950.00
from $2,950.00 / night
MAKENA SURF RESORT, #E-104^
Wailea Apartment
- 2 bedrooms 2
- sleeps 4 4
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$559.00
from $559.00 / night
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