50 Best Wailea Condos on Holiday Lettings - Vacation rentals

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160 Vacation rentals

(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

from $200 / night

$1391 - $1900 / week

Book View

from $200 / night

(2) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

from $540 / night

$3780 - $6476 / week

Inquire View

from $540 / night

22

Maui / Wailea

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

from $120 / night

$834 / week

Book View

from $120 / night

(8) Excellent 

14

Maui / Wailea

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

from $160 / night

$1300 - $1440 / week

Book View

from $160 / night

(6) Excellent 

17

Maui / Wailea

1 4 4 nights min

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

from $220 / night

$1540 / week

Book View

from $220 / night

16

Maui / Wailea

2 4 Min stay varies

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

from $268 / night

$1869 - $3465 / week

Inquire View

from $268 / night

(1) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

from $776 / night

$5425 - $10151 / week

Inquire View

from $776 / night

(1) Excellent 

23

Maui / Wailea

1 4 Min stay varies

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

from $225 / night

$1575 / week

Book View

from $225 / night

(4) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

from $384 / night

$2681 - $4816 / week

Inquire View

from $384 / night

(16) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

from $384 / night

$2681 - $4816 / week

Inquire View

from $384 / night

16

Maui / Wailea

2 4 Min stay varies

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

from $384 / night

$2681 - $4816 / week

Inquire View

from $384 / night

(2) Excellent 

12

Maui / Wailea

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $245 / night

$1716 / week

Book View

from $245 / night

16

Maui / Wailea

2 4 Min stay varies

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

from $676 / night

$4725 - $8751 / week

Inquire View

from $676 / night

(4) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

from $612 / night

$4284 - $7176 / week

Inquire View

from $612 / night

(1) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

from $447 / night

$3123 - $5425 / week

Inquire View

from $447 / night

16

Maui / Wailea

1 2 Min stay varies

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

from $293 / night

$2052 - $3291 / week

Inquire View

from $293 / night

(16) Very Good 

16

Maui / Wailea

1 2 Min stay varies

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

from $376 / night

$2625 - $4432 / week

Inquire View

from $376 / night

(20) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

from $447 / night

$3123 - $5425 / week

Inquire View

from $447 / night

25

Maui / Wailea

1 4 1 night min

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

from $120 / night

$834 / week

Book View

from $120 / night

(16) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

from $540 / night

$3780 - $6476 / week

Inquire View

from $540 / night

(2) Very Good 

16

Maui / Wailea

1 2 Min stay varies

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

from $293 / night

$2052 - $3291 / week

Inquire View

from $293 / night

16

Maui / Wailea

2 4 Min stay varies

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

from $440 / night

$3080 - $5951 / week

Inquire View

from $440 / night

(9) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

from $384 / night

$2681 - $4816 / week

Inquire View

from $384 / night

(7) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

from $612 / night

$4284 - $7176 / week

Inquire View

from $612 / night

(7) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

from $400 / night

$2793 - $4816 / week

Inquire View

from $400 / night

26

Maui / Wailea

1 4 Min stay varies

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

from $336 / night

$2346 / week

Book View

from $336 / night

16

Maui / Wailea

1 2 Min stay varies

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

from $293 / night

$2052 - $3291 / week

Inquire View

from $293 / night

16

Maui / Wailea

2 4 Min stay varies

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

from $400 / night

$2793 - $5951 / week

Inquire View

from $400 / night

(1) Excellent 

24

Maui / Wailea

3 8 3 nights min

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

from $725 / night

$5075 / week

Book View

from $725 / night

(5) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

from $540 / night

$3780 - $6476 / week

Inquire View

from $540 / night

5

Maui / Wailea

1 2 Min stay varies

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

from $376 / night

$2625 - $4432 / week

Inquire View

from $376 / night

(1) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

from $600 / night

$4193 - $8751 / week

Inquire View

from $600 / night

(10) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

from $200 / night

$1393 - $2688 / week

Inquire View

from $200 / night

(8) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

from $384 / night

$2681 - $4816 / week

Inquire View

from $384 / night

16

Maui / Wailea

1 2 Min stay varies

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

from $180 / night

$1253 - $2380 / week

Inquire View

from $180 / night

(3) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

from $751 / night

$5251 - $7176 / week

Inquire View

from $751 / night

(11) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

from $600 / night

$4193 - $8400 / week

Inquire View

from $600 / night

18

Maui / Wailea

2 6 Min stay varies

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

from $451 / night

$2905 - $3745 / week

Inquire View

from $451 / night

(37) Excellent 

20

Maui / Wailea

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

from $576 / night

$4376 - $6965 / week

Book View

from $576 / night

(17) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

from $384 / night

$2681 - $4816 / week

Inquire View

from $384 / night

1