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.

Filter by Region:

Filter by Amenities:

Filter by Entertainment:

Filter resultsGo Reset filtersReset Close
  1. VILLA
    3BD Fairways Villa (116C) at Four Seasons Resort Hualalai

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

    Kailua Kona, HI

    Pool Hot Tub

    $970 to $2,858/night

  2. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/night

  3. CONDOMINIUM
    Kona 2 Bedroom

    Kona 2 Bedroom

    Kailua-Kona, HI

    Pool Hot Tub
  4. CONDOMINIUM
    Bali Hai Villas 2 Bedroom

    Bali Hai Villas 2 Bedroom

    Princeville, HI

    Pool Hot Tub
  5. CONDOMINIUM
    Kauai Beach Villas 2 Bedroom

    Kauai Beach Villas 2 Bedroom

    Lihue, HI

    Pool
  6. CONDOMINIUM
    Plantations at Princeville #1122

    Plantations at Princeville #1122

    Princeville, HI

    Pool

    $259 to $311/night

  7. CONDOMINIUM
    Plantations at Princeville #111

    Plantations at Princeville #111

    Princeville, HI

    Pool

    $206 to $311/night

  8. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool

    $456 to $572/night

  9. CONDOMINIUM
    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    Kapaa, HI

    Pool

    $456 to $572/night

  10. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Pool
    FREE CANCELLATION

    $322 to $435/night

  11. CONDOMINIUM
    Close to the Beach, Shopping and Adventures! 3 Bed Condo

    Close to the Beach, Shopping and Adventures! 3 Bed Condo...

    Kohala Coast, HI

    Pool Hot Tub
    FREE CANCELLATION

    $280 to $426/night

  12. CONDOMINIUM
    Kaanapali Shores Studio 642

    Kaanapali Shores Studio 642

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $371/night

  13. CONDOMINIUM
    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  14. CONDOMINIUM
    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  15. CONDOMINIUM
    Waikiki Beach Walk 1 Bedroom

    Waikiki Beach Walk 1 Bedroom

    Honolulu, HI

    Pool Hot Tub
  16. CONDOMINIUM
    Wailea Elua #2110

    Wailea Elua #2110

    Wailea, HI

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $725/night

  17. CONDOMINIUM
    Hale Ono Loa 409

    Hale Ono Loa 409

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $961/night

  18. CONDOMINIUM
    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $467/night

  19. CONDOMINIUM
    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $431/night

  20. CONDOMINIUM
    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    Kapolei, HI

    Pool Hot Tub

    $420 to $1,500/night

  21. CONDOMINIUM
    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Kapolei, HI

    Pool Hot Tub

    $501 to $1,668/night

  22. CONDOMINIUM
    Hali'i Kai 15A at the Waikoloa Beach Resort

    Hali'i Kai 15A at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $316 to $1,060/night

  23. TOWNHOUSE
    Mauna Lani Fairways #803

    Mauna Lani Fairways #803

    Mauna Lani, HI

    Pool Hot Tub
    FREE CANCELLATION

    $203 to $678/night

  24. CONDOMINIUM
    Hali'i Kai 12H at the Waikoloa Beach Resort

    Hali'i Kai 12H at the Waikoloa Beach Resort

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $386 to $1,125/night

  25. HOUSE
    Fairway Villas I34 at the Waikoloa Beach Resort

    Fairway Villas I34 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $536/night

  26. HOUSE
    Fairway Villas I33 at the Waikoloa Beach Resort

    Fairway Villas I33 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $536/night

  27. TOWNHOUSE
    Mauna Lani Fairways #403

    Mauna Lani Fairways #403

    Mauna Lani, HI

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $650/night

  28. CONDOMINIUM
    Fairway Villas D5 at the Waikoloa Beach Resort

    Fairway Villas D5 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $125 to $466/night

  29. CONDOMINIUM
    Palm Villas (H23) at Mauna Lani 2 Bedrooms + Loft

    Palm Villas (H23) at Mauna Lani 2 Bedrooms + Loft

    Kamuela, HI

    Pool Hot Tub

    $387 to $922/night

  30. APARTMENT
    Maui Lani Terraces A205

    Maui Lani Terraces A205

    Lahaina, HI

    Pool

    $243 to $527/night

  31. CONDOMINIUM
    Vista Waikoloa B-302

    Vista Waikoloa B-302

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $488/night

  32. CONDOMINIUM
    Kapalua Bay Villa 32B2 Gold Ocean View

    Kapalua Bay Villa 32B2 Gold Ocean View

    Kapalua, HI

    Pool

    $531 to $969/night

  33. CONDOMINIUM
    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2b

    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2...

    Kaanapali, HI

    Pool Hot Tub

    $616 to $2,355/night

  34. CONDOMINIUM
    Kapalua Bay Villa 11B3-4 Gold Ocean View

    Kapalua Bay Villa 11B3-4 Gold Ocean View

    Kapalua, HI

    Pool

    $406 to $781/night

  35. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  36. CONDOMINIUM
    Honua Kai- Konea 643- Two Bed Ocean Views! 2b/2b

    Honua Kai- Konea 643- Two Bed Ocean Views! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $406 to $1,543/night

  37. CONDOMINIUM
    Royal Kahana 107 1Bdrm

    Royal Kahana 107 1Bdrm

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $346/night

  38. CONDOMINIUM
    Royal Kahana #209

    Royal Kahana #209

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $215 to $481/night

  39. CONDOMINIUM
    Hear the Waves!! Honua Kai- Hokulani 306

    Hear the Waves!! Honua Kai- Hokulani 306

    Kaanapali, HI

    Pool Hot Tub

    $394 to $1,511/night

  40. CONDOMINIUM
    E3-1 Bedroom Oceanfront

    E3-1 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $259 to $428/night

  41. CONDOMINIUM
    Papakea A309

    Papakea A309

    Lahaina, HI

    Pool Hot Tub

    $208 to $357/night

  42. CONDOMINIUM
    Honua Kai- Konea 642- Ocean View from inside! 2b/2b

    Honua Kai- Konea 642- Ocean View from inside! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $406 to $1,543/night

  43. CONDOMINIUM
    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $445/night

  44. CONDOMINIUM
    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Kapolei, HI

    Pool Hot Tub

    $613 to $1,668/night

  45. CONDOMINIUM
    Ridge Villa 1422

    Ridge Villa 1422

    LAHAINA, HI

    Pool Hot Tub

    $197 to $248/night

  46. 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

  47. CONDOMINIUM
    Kamaole Sands #06-106

    Kamaole Sands #06-106

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $332/night

  48. CONDOMINIUM
    Maui Kaanapali Villas #B231

    Maui Kaanapali Villas #B231

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $232 to $331/night

  49. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Pool Hot Tub
    FREE CANCELLATION

    $257 to $306/night

  50. CONDOMINIUM
    Maui Kaanapali Villas #E290

    Maui Kaanapali Villas #E290

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $220 to $418/night

  51. CONDOMINIUM
    Sands Of Kahana 272

    Sands Of Kahana 272

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  52. CONDOMINIUM
    Maui Kaanapali Villas #E288

    Maui Kaanapali Villas #E288

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $220 to $377/night

  53. CONDOMINIUM
    Pohailani #133

    Pohailani #133

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $184 to $409/night

  54. CONDOMINIUM
    Mokuleia Sands #308

    Mokuleia Sands #308

    Waialua, HI

    $77 to $81/night

  55. CONDOMINIUM
    Maui Kaanapali Villas #D275

    Maui Kaanapali Villas #D275

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $319 to $510/night

  56. CONDOMINIUM
    Royal Kahana #617

    Royal Kahana #617

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $139 to $377/night

  57. HOUSE
    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  58. CONDOMINIUM
    Maui Kaanapali Villas #A116

    Maui Kaanapali Villas #A116

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $186 to $365/night

  59. CONDOMINIUM
    Kahana Sunset D10

    Kahana Sunset D10

    Lahaina, HI

    Pool

    $253 to $309/night

  60. CONDOMINIUM
    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    Lahaina, HI

    Pool Hot Tub

    $236 to $304/night

  61. CONDOMINIUM
    Kahana Sunset D2

    Kahana Sunset D2

    Lahaina, HI

    Pool

    $276 to $332/night

  62. CONDOMINIUM
    Napili Point A8

    Napili Point A8

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $219 to $469/night

  63. CONDOMINIUM
    Honua Kai- Hokulani 612- Great Ocean View! 2b/2b

    Honua Kai- Hokulani 612- Great Ocean View! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $383 to $1,511/night

  64. CONDOMINIUM
    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night

  65. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Pool

    $371 to $484/night

  66. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $521/night

  67. CONDOMINIUM
    Fairway Villas L21 at the Waikoloa Beach Resort

    Fairway Villas L21 at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool
    FREE CANCELLATION

    $250 to $495/night

  68. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $215 to $423/night

  69. CONDOMINIUM
    Whaler at Kaanapali Beach 1173

    Whaler at Kaanapali Beach 1173

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $849 to $1,169/night

  70. CONDOMINIUM
    Ilikai #1743

    Ilikai #1743

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $404 to $619/night

  71. CONDOMINIUM
    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua, HI

    Pool

    $369 to $594/night

  72. CONDOMINIUM
    Papakea A108

    Papakea A108

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  73. CONDOMINIUM
    Wailea Ekolu 1606

    Wailea Ekolu 1606

    Kihei, HI

    Pool
    FREE CANCELLATION

    $401 to $610/night

  74. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Pool Hot Tub

    $548 to $1,784/night

  75. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $274 to $381/night

  76. CONDOMINIUM
    Kamaole Sands #1-103

    Kamaole Sands #1-103

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $168 to $278/night

  77. CONDOMINIUM
    Kamaole Sands #10-405

    Kamaole Sands #10-405

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $393 to $480/night

  78. CONDOMINIUM
    Kaanapali Shores #160

    Kaanapali Shores #160

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $429 to $800/night

  79. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $469 to $776/night

  80. CONDOMINIUM
    Honua Kai- Konea 312- One Plus Den- Sleeps 6! 2b/1b

    Honua Kai- Konea 312- One Plus Den- Sleeps 6! 2b/1b

    Kaanapali, HI

    Pool Hot Tub

    $316 to $1,121/night

  81. 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

  82. CONDOMINIUM
    Maui Sunset #A-204

    Maui Sunset #A-204

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $266/night

  83. CONDOMINIUM
    Maui Kamaole #I-215

    Maui Kamaole #I-215

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $377/night

  84. CONDOMINIUM
    Sands Of Kahana 231

    Sands Of Kahana 231

    Lahaina, HI

    Pool Hot Tub

    $208 to $253/night

  85. CONDOMINIUM
    Kamaole Sands #06-307

    Kamaole Sands #06-307

    KIHEI, HI

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $332/night

  86. CONDOMINIUM
    Mauna Lani Golf Villas Q2

    Mauna Lani Golf Villas Q2

    Kamuela, HI

    Pool

    $304 to $661/night

  87. CONDOMINIUM
    Mahana 713

    Mahana 713

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $246 to $680/night

  88. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $163 to $269/night

  89. 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

  90. CONDOMINIUM
    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali, HI

    Pool Hot Tub

    $322 to $1,153/night

  91. CONDOMINIUM
    Papakea A307

    Papakea A307

    Lahaina, HI

    Pool Hot Tub

    $245 to $381/night

  92. CONDOMINIUM
    Whaler at Kaanapali Beach 912

    Whaler at Kaanapali Beach 912

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $602 to $764/night

  93. 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

  94. CONDOMINIUM
    Papakea J103

    Papakea J103

    Lahaina, HI

    Pool Hot Tub

    $196 to $351/night

  95. HOUSE
    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  96. CONDOMINIUM
    E4-2 Bedroom Oceanfront

    E4-2 Bedroom Oceanfront

    Kihei, HI

    Pool
    FREE CANCELLATION

    $377 to $591/night

  97. VILLA
    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps To Beach

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps ...

    Kihei, HI

    $1,618 to $26,094/night

  98. CONDOMINIUM
    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To Beach

    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To B...

    Kihei, HI

    Pool Hot Tub

    $173 to $786/night

  99. CONDOMINIUM
    Honua kai- Konea 1026- 2 bedroom Partial Ocean View

    Honua kai- Konea 1026- 2 bedroom Partial Ocean View

    Lahaina, HI

    Pool Hot Tub

    $389 to $1,446/night

  100. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Pool
    FREE CANCELLATION

    $304 to $540/night