50 Best Wailea Condos on Holiday Lettings - Vacation rentals

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161 Vacation rentals

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

(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 

25

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 $177 / night

$1235 - $1835 / week

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from $177 / night

(10) Excellent 

23

Maui / Wailea

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $365 / night

$2555 - $4200 / week

Inquire View

from $365 / night

18

Maui / Wailea

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $415 / night

$2905 - $3745 / week

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from $415 / night

(7) Excellent 

19

Maui / Wailea

Studio 8 Min stay varies

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

 …see more

from $810 / night

$6160 - $11165 / week

Inquire View

from $810 / night

(2) Very Good 

13

Maui / Wailea

Studio 2 Min stay varies

  • Studio
  • 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

22

Maui / Wailea

Studio 4 Min stay varies

  • Studio
  • 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

(3) Excellent 

17

Maui / Wailea

Studio 4 Min stay varies

  • Studio
  • 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

22

Maui / Wailea

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Ask about pets

 …see more

from $246 / night

$1553 - $3183 / week

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from $246 / night

(3) Very Good 

19

Maui / Wailea

Studio 2 Min stay varies

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

 …see more

from $230 / night

$1610 - $2170 / week

Inquire View

from $230 / night

(13) Excellent 

17

Maui / Wailea

Studio 5 Min stay varies

  • Studio
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $235 / night

$1645 - $2170 / week

Inquire View

from $235 / 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

(2) Good 

16

Maui / Wailea

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $360 / night

$2520 - $3395 / week

Inquire View

from $360 / night

(2) Very Good 

20

Maui / Wailea

Studio 2 Min stay varies

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

 …see more

from $325 / night

$2275 - $2765 / week

Inquire View

from $325 / night

(3) Very Good 

18

Maui / Wailea

Studio 4 Min stay varies

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

 …see more

from $220 / night

$1540 - $2170 / week

Inquire View

from $220 / night

(1) Very Good 

22

Maui / Wailea

Studio 4 Min stay varies

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

 …see more

from $225 / night

$1575 - $2135 / week

Inquire View

from $225 / night

25

Maui / Wailea

Studio 4 Min stay varies

  • Studio
  • 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

(4) Excellent 

19

Maui / Wailea

Studio 4 Min stay varies

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

 …see more

from $325 / night

$2275 - $2765 / week

Inquire View

from $325 / night

19

Maui / Wailea

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning

 …see more

from $255 / night

$1785 - $2520 / week

Inquire View

from $255 / night

(7) Excellent 

21

Maui / Wailea

Studio 8 Min stay varies

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

 …see more

from $810 / night

$6160 - $11165 / week

Inquire View

from $810 / night

(2) Very Good 

17

Maui / Wailea

Studio 4 Min stay varies

  • Studio
  • 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

18

Maui / Wailea

Studio 2 Min stay varies

  • Studio
  • 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

(2) Excellent 

18

Maui / Wailea

Studio 4 Min stay varies

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

 …see more

from $365 / night

$2555 - $3500 / week

Inquire View

from $365 / night

20

Maui / Wailea

Studio 4 Min stay varies

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

 …see more

from $270 / night

$1890 - $2765 / week

Inquire View

from $270 / 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

(4) Excellent 

24

Maui / Wailea

Studio 4 Min stay varies

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

 …see more

from $645 / night

$4515 - $5845 / week

Inquire View

from $645 / night

(1) Excellent 

24

Maui / Wailea

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly

 …see more

from $731 / night

$5116 / week

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from $731 / night

16

Maui / Wailea

Studio 5 Min stay varies

  • Studio
  • Sleeps 5
  • Min stay varies
  • Ask about children

 …see more

from $440 / night

$3080 - $5950 / week

Inquire View

from $440 / night

(6) Excellent 

16

Maui / Wailea

Studio 2 Min stay varies

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

 …see more

from $190 / night

$1330 - $1925 / week

Inquire View

from $190 / night

(5) Very Good 

16

Maui / Wailea

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $540 / night

$3780 - $6475 / week

Inquire View

from $540 / night

27

Maui / Wailea

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $435 / night

$3045 - $4305 / week

Inquire View

from $435 / night

(1) Excellent 

19

Maui / Wailea

Studio 2 Min stay varies

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

 …see more

from $250 / night

$1750 - $2345 / week

Inquire View

from $250 / night

(2) Very Good 

19

Maui / Wailea

Studio 4 Min stay varies

  • Studio
  • 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

(4) Very Good 

16

Maui / Wailea

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Ask about children

 …see more

from $383 / night

$2681 - $4816 / week

Inquire View

from $383 / night

(4) Excellent 

25

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

 …see more

from $197 / night

$1377 - $2400 / week

Book View

from $197 / 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

(3) Very Good 

23

Maui / Wailea

Studio 4 Min stay varies

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

 …see more

from $285 / night

$1995 - $2520 / week

Inquire View

from $285 / 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

Book View

from $192 / night

(16) Very Good 

16

Maui / Wailea

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Ask about children

 …see more

from $375 / night

$2625 - $4431 / week

Inquire View

from $375 / night

16

Maui / Wailea

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Ask about children

 …see more

from $440 / night

$3080 - $5950 / week

Inquire View

from $440 / night

1