50 Best Wailea Condos on Holiday Lettings - Vacation rentals

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157 Vacation rentals

Travelers going to Wailea are booking March dates now. Secure your vacation rental today and have the perfect trip.

(5) Excellent 

14

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $200 / night

$1400 - $1855 / week

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from $200 / night

(18) Excellent 

25

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Car not necessary

 …see more

from $201 / night

$1402 - $1916 / week

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from $201 / night

(1) Excellent 

29

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly

 …see more

from $175 / night

$1225 - $1820 / week

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from $175 / night

0

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $545 / night

$3811 - $6528 / week

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from $545 / night

(4) Excellent 

0

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $617 / night

$4319 - $7233 / week

Inquire View

from $617 / night

(1) Excellent 

15

Maui / Wailea

2 8 4 nights min

  • 2 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 1 mi
  • Child friendly

 …see more

from $192 / night

$1311 - $1593 / week

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from $192 / night

(7) Excellent 

19

Maui / Wailea

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $810 / night

$6160 - $11165 / week

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from $810 / night

(2) Excellent 

18

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $365 / night

$2555 - $3500 / week

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from $365 / night

(3) Very Good 

23

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $285 / night

$1995 - $2520 / week

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from $285 / night

13

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $190 / night

$1330 - $1890 / week

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from $190 / night

(17) Excellent 

0

Maui / Wailea

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children

 …see more

from $387 / night

$2703 - $4855 / week

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from $387 / night

(18) Very Good 

14

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $220 / night

$1540 - $2030 / week

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from $220 / night

(3) Excellent 

17

Maui / Wailea

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $222 / night

$1553 / week

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from $222 / night

(5) Excellent 

16

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $190 / night

$1330 - $1925 / week

Inquire View

from $190 / night

(16) Excellent 

0

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $545 / night

$3811 - $6528 / week

Inquire View

from $545 / night

21

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

 …see more

from $191 / night

$1334 / week

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from $191 / night

(3) Very Good 

18

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $220 / night

$1540 - $2170 / week

Inquire View

from $220 / night

(7) Excellent 

58

Maui / Wailea

Studio 6 5 nights min

  • Studio
  • Sleeps 6
  • 5 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $1095 / night

$7665 / week

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from $1095 / night

0

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children

 …see more

from $463 / night

$3239 - $6408 / week

Inquire View

from $463 / night

(2) Very Good 

20

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $260 / night

$1820 - $2415 / week

Inquire View

from $260 / night

(2) Excellent 

0

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $545 / night

$3811 - $6528 / week

Inquire View

from $545 / night

(3) Excellent 

17

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $235 / night

$1645 - $2170 / week

Inquire View

from $235 / night

(7) Very Good 

0

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $617 / night

$4319 - $7233 / week

Inquire View

from $617 / night

(16) Excellent 

0

Maui / Wailea

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children

 …see more

from $387 / night

$2703 - $4855 / week

Inquire View

from $387 / night

(3) Very Good 

82

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

 …see more

from $197 / night

$1377 / week

Book View

from $197 / night

0

Maui / Wailea

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $270 / night

$1885 - $3493 / week

Inquire View

from $270 / night

(2) Very Good 

0

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children

 …see more

from $296 / night

$2068 - $3317 / week

Inquire View

from $296 / night

22

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $235 / night

$1645 - $2170 / week

Inquire View

from $235 / night

(2) Very Good 

19

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $235 / night

$1645 - $2170 / week

Inquire View

from $235 / night

15

Maui / Wailea

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $1608 / night

$11256 - $33131 / week

Inquire View

from $1608 / night

18

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $265 / night

$1855 - $2450 / week

Inquire View

from $265 / night

(1) Excellent 

19

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $250 / night

$1750 - $2345 / week

Inquire View

from $250 / night

0

Maui / Wailea

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children

 …see more

from $444 / night

$3105 - $5998 / week

Inquire View

from $444 / night

(3) Very Good 

0

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $757 / night

$5293 - $7233 / week

Inquire View

from $757 / night

(2) Very Good 

13

Maui / Wailea

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $210 / night

$1470 - $1925 / week

Inquire View

from $210 / night

0

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $617 / night

$4319 - $7233 / week

Inquire View

from $617 / night

(1) Excellent 

23

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $227 / night

$1588 / week

Book View

from $227 / night

25

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $315 / night

$2205 - $2765 / week

Inquire View

from $315 / night

(2) Excellent 

20

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $285 / night

$1995 - $2590 / week

Inquire View

from $285 / night

0

Maui / Wailea

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $617 / night

$4319 - $7233 / week

Inquire View

from $617 / night