50 Best Wailea Condos on Holiday Lettings - Vacation rentals

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151 Vacation rentals

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(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 $195 / night

$1365 - $1821 / week

Inquire View

from $195 / 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 $190 / night

$1324 / week

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from $190 / 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 - $1821 / week

Inquire View

from $190 / night

(16) Excellent 

16

Maui / Wailea

2 6 Min stay varies

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

 …see more

from $499 / night

$3494 - $6475 / week

Inquire View

from $499 / 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 $190 / night

$1300 / week

Book View

from $190 / night

(7) Excellent 

16

Maui / Wailea

2 6 Min stay varies

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

 …see more

from $426 / night

$2976 - $4817 / week

Inquire View

from $426 / night

(6) Excellent 

16

Maui / Wailea

2 6 Min stay varies

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

 …see more

from $384 / night

$2682 - $4817 / week

Inquire View

from $384 / night

(8) Very Good 

16

Maui / Wailea

2 4 Min stay varies

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

 …see more

from $384 / night

$2682 - $4817 / week

Inquire View

from $384 / night

(16) Excellent 

16

Maui / Wailea

2 5 Min stay varies

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

 …see more

from $384 / night

$2682 - $4817 / week

Inquire View

from $384 / night

(13) Excellent 

17

Maui / Wailea

2 5 Min stay varies

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

 …see more

from $225 / night

$1575 - $2135 / week

Inquire View

from $225 / 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 - $1995 / week

Inquire View

from $220 / 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 $446 / night

$3123 - $5426 / week

Inquire View

from $446 / night

(17) Very Good 

16

Maui / Wailea

1 4 Min stay varies

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

 …see more

from $421 / night

$2941 - $5586 / week

Inquire View

from $421 / 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 - $2521 / week

Inquire View

from $285 / 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

 …see more

from $190 / night

$1300 - $1744 / week

Book View

from $190 / night

(7) Excellent 

21

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

$5671 - $11166 / week

Inquire View

from $810 / 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 $499 / night

$3494 - $6475 / week

Inquire View

from $499 / night

(10) Excellent 

16

Maui / Wailea

2 4 Min stay varies

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

 …see more

from $441 / night

$3081 - $5950 / week

Inquire View

from $441 / 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 $299 / night

$2093 - $4431 / week

Inquire View

from $299 / night

16

Maui / Wailea

2 5 Min stay varies

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

 …see more

from $441 / night

$3081 - $5950 / week

Inquire View

from $441 / 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 - $2521 / week

Inquire View

from $285 / night

(9) Very Good 

16

Maui / Wailea

2 6 Min stay varies

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

 …see more

from $384 / night

$2682 - $4817 / week

Inquire View

from $384 / night

(2) Very Good 

20

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 $326 / night

$2276 - $2695 / week

Inquire View

from $326 / night

16

Maui / Wailea

1 2 Min stay varies

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

 …see more

from $459 / night

$3213 - $6356 / week

Inquire View

from $459 / 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 $250 / night

$1751 - $3465 / week

Inquire View

from $250 / night

(1) Excellent 

24

Maui / Wailea

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly

 …see more

from $725 / night

$5075 / week

Book View

from $725 / 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

$1751 - $2311 / week

Inquire View

from $250 / night

(17) Excellent 

16

Maui / Wailea

2 5 Min stay varies

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

 …see more

from $384 / night

$2682 - $5950 / week

Inquire View

from $384 / 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 $436 / night

$3046 - $4236 / week

Inquire View

from $436 / 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 $285 / night

$1995 - $2555 / week

Inquire View

from $285 / night

(8) 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 $499 / night

$3494 - $6475 / week

Inquire View

from $499 / night

(7) 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 $613 / night

$4284 - $7175 / week

Inquire View

from $613 / night

(4) Excellent 

19

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 $326 / night

$2276 - $2695 / week

Inquire View

from $326 / 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 $225 / night

$1575 / week

Book View

from $225 / night

(3) Very Good 

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 $220 / night

$1540 - $2135 / week

Inquire View

from $220 / night

(3) Excellent 

21

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 $386 / night

$2695 - $3255 / week

Inquire View

from $386 / 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 $476 / night

$3325 - $4376 / week

Inquire View

from $476 / 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 $205 / night

$1435 - $1856 / week

Inquire View

from $205 / night

(4) Excellent 

24

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 $621 / night

$4341 - $5671 / week

Inquire View

from $621 / 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 $190 / night

$1226 - $1821 / week

Book View

from $190 / night