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
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    Pool
    FREE CANCELLATION

    $235 to $367/night

  2. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  3. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  4. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  5. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,524 to $5,243/night

  6. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $817 to $934/night

  7. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $397 to $409/night

  8. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $760/night

  9. HOUSE
    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $219 to $600/night

  10. CONDOMINIUM
    Pohailani #223

    Pohailani #223

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $184 to $409/night

  11. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  12. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $310/night

  13. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Pool
    FREE CANCELLATION

    $186 to $275/night

  14. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $331/night

  15. CONDOMINIUM
    Kaanapali Shores 942

    Kaanapali Shores 942

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $211 to $498/night

  16. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $304/night

  17. CONDOMINIUM
    Papakea J107

    Papakea J107

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $178 to $498/night

  18. CONDOMINIUM
    Maui Banyan Q306

    Maui Banyan Q306

    Kihei, HI

    Pool
    FREE CANCELLATION

    $203 to $448/night

  19. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $221 to $423/night

  20. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $211 to $435/night

  21. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,668/night

  22. HOUSE
    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $473 to $842/night

  23. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Pool Hot Tub

    $342 to $646/night

  24. CONDOMINIUM
    Kaleialoha 210

    Kaleialoha 210

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $191 to $299/night

  25. CONDOMINIUM
    Island Surf 409

    Island Surf 409

    Kihei, HI

    Pool
    FREE CANCELLATION

    $186 to $455/night

  26. CONDOMINIUM
    Kihei Akahi C-616

    Kihei Akahi C-616

    Kihei, HI

    Pool
    FREE CANCELLATION

    $174 to $468/night

  27. HOUSE
    Mahuahua Hale

    Mahuahua Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $525 to $642/night

  28. HOUSE
    Heeia Bay Hale

    Heeia Bay Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $407 to $466/night

  29. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,256 to $1,395/night

  30. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,142 to $1,536/night

  31. CONDOMINIUM
    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $238 to $384/night

  32. CONDOMINIUM
    Kaleialoha 205

    Kaleialoha 205

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $194 to $331/night

  33. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $214 to $474/night

  34. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $153 to $459/night

  35. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $203 to $345/night

  36. CONDOMINIUM
    Kihei Alii Kai A207

    Kihei Alii Kai A207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $438/night

  37. CONDOMINIUM
    Paki Maui 424

    Paki Maui 424

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $300 to $813/night

  38. CONDOMINIUM
    Kahana Manor 410

    Kahana Manor 410

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $193 to $325/night

  39. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

  40. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kailua Kona, HI

    Pool
  41. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  42. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  43. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $521/night

  44. CONDOMINIUM
    Kamaole Sands 5-313

    Kamaole Sands 5-313

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $168 to $438/night

  45. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $303/night

  46. CONDOMINIUM
    Kihei Alii Kai A101

    Kihei Alii Kai A101

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $526/night

  47. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $345/night