Search 105,200+ Vacation Rentals

Wailea Vacation Rentals & Apartments with Swimming Pool - 199 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

199 Vacation rentals

Filters applied: Swimming pool

(98)

1 / 42

Wailea Villa

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$895.00

Excellent (98 reviews)

Inquire

from $895.00 / night

1 / 20

Wailea Condo

  • 2
  • 6
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$159.00

Book

from $159.00 / night

1 / 15

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$486.00

Inquire

from $486.00 / night

(4)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Excellent (4 reviews)

Inquire

from $612.00 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$699.00

Excellent (1 reviews)

Inquire

from $699.00 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$267.00

Excellent (1 reviews)

Inquire

from $267.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Inquire

from $612.00 / night

(13)

1 / 16

Wailea Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$250.00

Very Good (13 reviews)

Inquire

from $250.00 / night

1 / 16

Wailea Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$198.00

Inquire

from $198.00 / night

(1)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$775.00

Excellent (1 reviews)

Inquire

from $775.00 / night

(5)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$540.00

Very Good (5 reviews)

Inquire

from $540.00 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Very Good (7 reviews)

Inquire

from $612.00 / night

(8)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$486.00

Very Good (8 reviews)

Inquire

from $486.00 / night

(3)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$750.00

Very Good (3 reviews)

Inquire

from $750.00 / night

(2)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$540.00

Excellent (2 reviews)

Inquire

from $540.00 / night

(20)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$447.00

Very Good (20 reviews)

Inquire

from $447.00 / night

(1)

1 / 23

Wailea Condo

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Air conditioning

$199.00

Excellent (1 reviews)

Inquire

from $199.00 / night

1 / 23

Wailea Villa

  • 3
  • 8
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

$1,649.00

Book

from $1,649.00 / night

(16)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$540.00

Excellent (16 reviews)

Inquire

from $540.00 / night

(14)

1 / 16

Wailea Apartment

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Very Good (14 reviews)

Inquire

from $612.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$200.00

Inquire

from $200.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$540.00

Inquire

from $540.00 / night

(10)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$250.00

Very Good (10 reviews)

Inquire

from $250.00 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Very Good (7 reviews)

Inquire

from $612.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$395.00

Inquire

from $395.00 / night

(7)

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Very Good (7 reviews)

Inquire

from $612.00 / night

1 / 16

Wailea Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$599.00

Inquire

from $599.00 / night

1 / 16

Wailea Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$384.00

Inquire

from $384.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$539.00

Inquire

from $539.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Inquire

from $612.00 / night

1 / 16

Wailea Apartment

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$447.00

Inquire

from $447.00 / night

1 / 16

Wailea Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$265.00

Inquire

from $265.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$809.00

Inquire

from $809.00 / night

1 / 16

Wailea Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$612.00

Inquire

from $612.00 / night

1 / 25

Wailea Villa

  • 3
  • 6
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

$2,599.00

Book

from $2,599.00 / night