50 Best Wailea Condos on Holiday Lettings - Vacation rentals

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164 Vacation rentals

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(4) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

 …see more

from $618 / night

$4320 - $7234 / week

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from $618 / night

24

Maui / Wailea

2 6 Min stay varies

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

 …see more

from $212 / night

$1341 - $2647 / week

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from $212 / night

(21) Very Good 

16

Maui / Wailea

1 4 Min stay varies

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

 …see more

from $500 / night

$3494 - $4905 / week

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from $500 / night

16

Maui / Wailea

1 2 Min stay varies

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

 …see more

from $463 / night

$3240 - $6409 / week

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from $463 / night

(3) Excellent 

35

Maui / Wailea

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

 …see more

from $242 / night

$1694 - $2576 / week

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from $242 / night

(13) Very Good 

16

Maui / Wailea

3 6 Min stay varies

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

 …see more

from $253 / night

$1765 - $3494 / week

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from $253 / night

(4) Excellent 

22

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 $196 / night

$1365 - $2380 / week

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from $196 / night

(6) Very Good 

24

Maui / Wailea

2 6 Min stay varies

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

 …see more

from $182 / night

$1200 - $2471 / week

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from $182 / night

24

Maui / Wailea

2 4 Min stay varies

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

 …see more

from $167 / night

$1094 - $2435 / week

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from $167 / night

(16) Excellent 

16

Maui / Wailea

2 5 Min stay varies

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

 …see more

from $387 / night

$2703 - $4856 / week

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from $387 / 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) 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 $263 / night

$1835 - $2188 / week

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from $263 / night

(1) Excellent 

10

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $149 / night

$1043 - $1393 / week

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from $149 / night

(16) Very Good 

16

Maui / Wailea

1 4 Min stay varies

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

 …see more

from $379 / night

$2647 - $4468 / week

Inquire View

from $379 / 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 $177 / night

$1236 - $1835 / week

Book View

from $177 / 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 $227 / night

$1588 - $1906 / week

Inquire View

from $227 / 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 $368 / night

$2576 - $3282 / week

Inquire View

from $368 / night

(17) Excellent 

16

Maui / Wailea

2 5 Min stay varies

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

 …see more

from $387 / night

$2703 - $4856 / week

Inquire View

from $387 / night

(2) Very Good 

16

Maui / Wailea

2 6 Min stay varies

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

 …see more

from $253 / night

$1765 - $2153 / week

Inquire View

from $253 / night

(1) Excellent 

16

Maui / Wailea

2 5 Min stay varies

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

 …see more

from $450 / night

$3148 - $5470 / week

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from $450 / 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 $288 / night

$2012 - $2329 / week

Inquire View

from $288 / 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

(2) 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

Book View

from $222 / night

(2) Excellent 

16

Maui / Wailea

2 5 Min stay varies

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

 …see more

from $545 / night

$3811 - $6529 / week

Inquire View

from $545 / night

18

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $419 / night

$2929 - $3494 / week

Inquire View

from $419 / night

(3) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

 …see more

from $618 / night

$4320 - $7234 / week

Inquire View

from $618 / night

27

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $439 / night

$3070 - $4058 / week

Inquire View

from $439 / night

5

Maui / Wailea

1 2 Min stay varies

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

 …see more

from $379 / night

$2647 - $4468 / week

Inquire View

from $379 / night

(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 $202 / night

$1412 - $1730 / week

Inquire View

from $202 / night

(2) Excellent 

16

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 - $6529 / 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 $237 / night

$1659 - $1977 / week

Inquire View

from $237 / night

(1) Excellent 

23

Maui / Wailea

1 4 5 nights min

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

 …see more

from $227 / night

$1588 / week

Book View

from $227 / night

24

Maui / Wailea

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning

 …see more

from $1815 / night

$12704 - $17644 / week

Inquire View

from $1815 / night

(3) Excellent 

35

Maui / Wailea

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $135 / night

$941 / week

Book View

from $135 / night

(2) Very Good 

16

Maui / Wailea

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Swimming pool
  • Ask about children

 …see more

from $812 / night

$5682 - $6176 / week

Inquire View

from $812 / night

(2) Excellent 

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

(1) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

 …see more

from $681 / night

$4764 - $8822 / week

Inquire View

from $681 / night

(7) Excellent 

16

Maui / Wailea

2 6 Min stay varies

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

 …see more

from $429 / night

$3000 - $4856 / week

Inquire View

from $429 / night

(20) Very Good 

16

Maui / Wailea

2 6 Min stay varies

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

 …see more

from $450 / night

$3148 - $5470 / week

Inquire View

from $450 / 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 $222 / night

$1553 - $2012 / week

Inquire View

from $222 / night