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. TOWNHOUSE
    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $632/night

  2. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Pool Hot Tub

    $330 to $689/night

  3. CONDOMINIUM
    Casa De Emdeko 111

    Casa De Emdeko 111

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $281 to $309/night

  4. CONDOMINIUM
    Casa De Emdeko 204

    Casa De Emdeko 204

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $165 to $186/night

  5. CONDOMINIUM
    Casa De Emdeko 211

    Casa De Emdeko 211

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $326 to $337/night

  6. CONDOMINIUM
    Casa De Emdeko 330

    Casa De Emdeko 330

    Kailua Kona, HI

    Pool
    FREE CANCELLATION
  7. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2503

    Colony Villas at Waikoloa Beach Resort #2503

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  8. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $464/night

  9. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  10. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    FREE CANCELLATION

    $471 to $683/night

  11. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    FREE CANCELLATION

    $347 to $466/night

  12. HOUSE
    Holoholo ku Waimea

    Holoholo ku Waimea

    Waimea, HI

    FREE CANCELLATION

    $193 to $255/night

  13. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  14. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $251 to $389/night

  15. CONDOMINIUM
    Kahana Villa F406 1Bdrm

    Kahana Villa F406 1Bdrm

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $191 to $346/night

  16. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  17. CONDOMINIUM
    Kaleialoha #114

    Kaleialoha #114

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  18. CONDOMINIUM
    Kaleialoha #115

    Kaleialoha #115

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  19. CONDOMINIUM
    Kaleialoha #204

    Kaleialoha #204

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $218 to $413/night

  20. CONDOMINIUM
    Kaleialoha #208

    Kaleialoha #208

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  21. CONDOMINIUM
    Kaleialoha #304

    Kaleialoha #304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $384/night

  22. CONDOMINIUM
    Kaleialoha #305

    Kaleialoha #305

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $168 to $289/night

  23. CONDOMINIUM
    Kaleialoha #312

    Kaleialoha #312

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $336/night

  24. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,524 to $5,243/night

  25. CONDOMINIUM
    Kamaole Sands #10-111

    Kamaole Sands #10-111

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $425/night

  26. CONDOMINIUM
    Kamaole Sands #10-312

    Kamaole Sands #10-312

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $348/night

  27. CONDOMINIUM
    Kamaole Sands #10-313

    Kamaole Sands #10-313

    Kihei, HI

    Pool
    FREE CANCELLATION

    $249 to $596/night

  28. CONDOMINIUM
    Kamaole Sands #5-103

    Kamaole Sands #5-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $360/night

  29. CONDOMINIUM
    Kamaole Sands #6-408

    Kamaole Sands #6-408

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $249 to $429/night

  30. CONDOMINIUM
    Kamaole Sands #9-207

    Kamaole Sands #9-207

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $273/night

  31. CONDOMINIUM
    Kanaloa 202

    Kanaloa 202

    Keauhou, HI

    Pool
    FREE CANCELLATION

    $169 to $230/night

  32. CONDOMINIUM
    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua, HI

    Pool

    $556 to $1,063/night

  33. CONDOMINIUM
    Kauai Beach Villas 2 Bedroom

    Kauai Beach Villas 2 Bedroom

    Lihue, HI

    Pool
  34. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  35. CONDOMINIUM
    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $181 to $242/night

  36. CONDOMINIUM
    Kona Pacific

    Kona Pacific

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $146 to $183/night

  37. CONDOMINIUM
    Kuleana 706 1 Bdrm

    Kuleana 706 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $256 to $461/night

  38. CONDOMINIUM
    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $190 to $633/night

  39. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  40. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $459/night

  41. CONDOMINIUM
    Maui Sunset #A-204

    Maui Sunset #A-204

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $266/night

  42. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $201 to $477/night

  43. CONDOMINIUM
    Maui Sunset #B-106

    Maui Sunset #B-106

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $412/night

  44. TOWNHOUSE
    Na Hale o Keauhou H3

    Na Hale o Keauhou H3

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $359/night

  45. CONDOMINIUM
    Noelani #219

    Noelani #219

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $381/night

  46. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $521/night

  47. CONDOMINIUM
    Ocean View w/Pool- Across from Kalama Beach

    Ocean View w/Pool- Across from Kalama Beach

    Kihei, HI

    Pool
    FREE CANCELLATION

    $146 to $378/night

  48. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Pool
    FREE CANCELLATION

    $138 to $316/night

  49. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  50. CONDOMINIUM
    Papakea A309

    Papakea A309

    Lahaina, HI

    Pool Hot Tub

    $208 to $357/night

  51. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    Pool Hot Tub

    $523 to $737/night

  52. CONDOMINIUM
    Papakea E306

    Papakea E306

    Lahaina, HI

    Pool Hot Tub

    $183 to $314/night

  53. CONDOMINIUM
    Papakea G206

    Papakea G206

    Lahaina, HI

    Pool Hot Tub

    $232 to $387/night

  54. CONDOMINIUM
    Papakea J103

    Papakea J103

    Lahaina, HI

    Pool Hot Tub

    $196 to $351/night

  55. CONDOMINIUM
    Papakea L405

    Papakea L405

    Lahaina, HI

    Pool Hot Tub

    $429 to $737/night

  56. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    FREE CANCELLATION

    $195 to $381/night

  57. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  58. CONDOMINIUM
    Plantations at Princeville #1122

    Plantations at Princeville #1122

    Princeville, HI

    Pool

    $259 to $311/night

  59. CONDOMINIUM
    Plantations at Princeville #521

    Plantations at Princeville #521

    Princeville, HI

    Pool

    $256 to $344/night

  60. CONDOMINIUM
    Pohailani 128

    Pohailani 128

    Lahaina, HI

    Pool

    $178 to $228/night

  61. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Pool
    FREE CANCELLATION

    $322 to $435/night

  62. CONDOMINIUM
    Royal Kahana 409 1 Bdrm

    Royal Kahana 409 1 Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $238 to $551/night

  63. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    FREE CANCELLATION

    $344 to $479/night

  64. CONDOMINIUM
    Valley Isle #1104

    Valley Isle #1104

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $173 to $375/night

  65. CONDOMINIUM
    Vista Waikoloa B-302

    Vista Waikoloa B-302

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $488/night

  66. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

  67. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  68. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  69. CONDOMINIUM
    Wailea Elua #2110

    Wailea Elua #2110

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $725/night

  70. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $632 to $1,015/night

  71. CONDOMINIUM
    Wailea Elua #701

    Wailea Elua #701

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $493 to $922/night

  72. CONDOMINIUM
    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    Kapaa, HI

    Pool

    $299 to $415/night

  73. CONDOMINIUM
    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    Kapaa, HI

    Pool

    $456 to $543/night

  74. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool

    $456 to $572/night