Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Beach bungalows, resort condos, and sun-kissed ocean-front villas await. Browse your island destination using the blue location links below or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process so you can have your vacation plans covered in no time.

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  1. CONDOMINIUM
    Wailea Elua Unit #0105

    Wailea Elua Unit #0105

    Wailea, HI

    Pool Hot Tub

    $459 to $953/night

  2. CONDOMINIUM
    Wailea Elua Unit #801

    Wailea Elua Unit #801

    Wailea, HI

    Pool Hot Tub

    $459 to $953/night

  3. CONDOMINIUM
    Wailea Elua Unit #0802

    Wailea Elua Unit #0802

    Wailea, HI

    Pool Hot Tub

    $437 to $953/night

  4. COTTAGE
    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    Kamuela, HI

    Pool Hot Tub

    $481 to $1,285/night

  5. HOUSE
    Kahakai Estates Hale

    Kahakai Estates Hale

    Kailua Kona, HI

    Pool Hot Tub

    $482 to $839/night

  6. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    Pool Hot Tub

    $899 to $2,487/night

  7. HOUSE
    Awapuhi Hale

    Awapuhi Hale

    Koloa, HI

    Pool Hot Tub

    $542 to $1,508/night

  8. CONDOMINIUM
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $338 to $919/night

  9. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $358 to $1,075/night

  10. CONDOMINIUM
    Cliffs 4206

    Cliffs 4206

    Princeville, HI

    Pool Hot Tub

    $241 to $301/night

  11. CONDOMINIUM
    Pali Ke Kua 203

    Pali Ke Kua 203

    Princeville, HI

    Pool Hot Tub

    $362 to $422/night

  12. CONDOMINIUM
    Plantation 1111

    Plantation 1111

    Princeville, HI

    Pool Hot Tub

    $241 to $271/night

  13. CONDOMINIUM
    Pali Ke Kua 10

    Pali Ke Kua 10

    Princeville, HI

    Pool Hot Tub

    $241 to $283/night

  14. CONDOMINIUM
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Pool Hot Tub

    $501 to $557/night

  15. CONDOMINIUM
    Sands Of Kahana 373

    Sands Of Kahana 373

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  16. CONDOMINIUM
    Cliffs 4205

    Cliffs 4205

    Princeville, HI

    Pool Hot Tub

    $235 to $301/night

  17. CONDOMINIUM
    Sea Village 4107

    Sea Village 4107

    Kailua Kona, HI

    Pool Hot Tub

    $275 to $799/night

  18. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  19. CONDOMINIUM
    Honua Kai- Konea 1019- Penthouse with private BBQ! 3b/3.5b

    Honua Kai- Konea 1019- Penthouse with private BBQ! 3b/3....

    Kaanapali, HI

    Pool Hot Tub

    $853 to $3,254/night

  20. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  21. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,917 to $5,992/night

  22. CONDOMINIUM
    Sandpiper 121B

    Sandpiper 121B

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $109 to $153/night

  23. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  24. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $1,179 to $1,664/night

  25. CONDOMINIUM
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  26. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $413/night

  27. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  28. VILLA
    3BD Fairways Villa (116D) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116D) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Pool Hot Tub

    $1,056 to $3,933/night

  29. CONDOMINIUM
    Honua Kai- Hokulani 509- Ocean view from INSIDE! 2b/2b

    Honua Kai- Hokulani 509- Ocean view from INSIDE! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $502 to $1,958/night

  30. CONDOMINIUM
    Honua Kai 506

    Honua Kai 506

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $608/night