RedAwning has over 350 Maui vacation homes and condos which all include instant online booking and no security deposits, to make your trip easy and stress-free. Maui is home to some of Hawaii’s most beautiful beaches and offers plenty of opportunities for adventure, from snorkeling with turtles to hiking through the bamboo forest to cliff diving in Hana. Book your stay today!

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  1. $3,288 to $12,005/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $289 to $979/night

    Wailea Ekahi 49F

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  5. $802 to $3,781/night

    Ho'olei 24-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $213 to $740/night

    Hale Kamaole 121

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $345 to $1,360/night

    Grand Champions 137

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $282 to $1,590/night

    Wailea Ekolu 502

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  13. $267 to $1,226/night

    Wailea Ekolu 1405

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  15. $231 to $830/night

    Maui Vista 2416

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  17. $981 to $4,324/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $304 to $1,334/night

    Wailea Ekolu 1507

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  21. $283 to $1,142/night

    Nohonani 102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  23. $250 to $687/night

    Hale Kai 115

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  25. $220 to $681/night

    Kamaole Sands 6-102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $305 to $1,166/night

    Valley Isle 708

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  29. $767 to $2,969/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $866 to $3,867/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $204 to $643/night

    Kihei Akahi C-507

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  35. $1,038 to $4,329/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $172 to $496/night

    Kihei Akahi C-317

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  39. $213 to $874/night

    Grand Champions 74

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $923 to $4,439/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  43. $243 to $841/night

    Grand Champions 68

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  45. $923 to $3,667/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $701 to $3,465/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  49. $396 to $1,728/night

    Wailea Ekahi 34B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  51. $1,038 to $5,010/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  53. $3,035 to $12,174/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  55. $274 to $1,192/night

    Wailea Ekolu 208

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  57. $231 to $954/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  59. $458 to $1,609/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  61. $306 to $1,329/night

    Wailea Ekolu 904

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  63. $469 to $1,784/night

    Wailea Ekahi 5E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  65. $268 to $1,074/night

    Grand Champions 36

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  67. $346 to $1,112/night

    Wailea Ekahi 48E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  69. $1,152 to $5,339/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  71. $923 to $4,073/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations