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. CONDOMINIUM
    Bay Villa 30G1

    Bay Villa 30G1

    Lahaina, HI

    Pool

    $248 to $304/night

  2. CONDOMINIUM
    Kahana Sunset A3

    Kahana Sunset A3

    Lahaina, HI

    Pool

    $326 to $383/night

  3. CONDOMINIUM
    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Pool

    $813 to $1,219/night

  4. CONDOMINIUM
    Hali'i Kai 14B at the Waikoloa Beach Resort

    Hali'i Kai 14B at the Waikoloa Beach Resort

    Waikoloa Beach Resort, HI

    Pool Hot Tub
    FREE CANCELLATION

    $363 to $989/night

  5. CONDOMINIUM
    Maui Kai 201

    Maui Kai 201

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $585/night

  6. CONDOMINIUM
    Country Club Villas #208

    Country Club Villas #208

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $154 to $480/night

  7. CONDOMINIUM
    Royal Sea Cliff #418

    Royal Sea Cliff #418

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $734/night

  8. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $608 to $791/night

  9. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  10. CONDOMINIUM
    Wavecrest A109

    Wavecrest A109

    Ualapue, HI

    Pool
    FREE CANCELLATION

    $124 to $169/night

  11. HOUSE
    OTA House

    OTA House

    Princeville, HI

    FREE CANCELLATION

    $219 to $280/night

  12. CONDOMINIUM
    Kaleialoha #315

    Kaleialoha #315

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $313/night

  13. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/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
    Sands Of Kahana 344

    Sands Of Kahana 344

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  17. CONDOMINIUM
    Sands Of Kahana 336

    Sands Of Kahana 336

    Lahaina, HI

    Pool Hot Tub

    $332 to $388/night

  18. CONDOMINIUM
    Maui Kai 506

    Maui Kai 506

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $411/night

  19. CONDOMINIUM
    Poipu Kapili 46

    Poipu Kapili 46

    Koloa, HI

    Pool
    FREE CANCELLATION

    $257 to $361/night

  20. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $294 to $413/night

  21. CONDOMINIUM
    Kahana Sunset F1

    Kahana Sunset F1

    Lahaina, HI

    Pool

    $428 to $484/night

  22. CONDOMINIUM
    Surf & Racquet Club 4302

    Surf & Racquet Club 4302

    Keauhou, HI

    Pool
    FREE CANCELLATION

    $279 to $401/night

  23. CONDOMINIUM
    Kahana Sunset F4

    Kahana Sunset F4

    Lahaina, HI

    Pool

    $428 to $484/night

  24. CONDOMINIUM
    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua, HI

    Pool

    $781 to $1,219/night

  25. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  26. CONDOMINIUM
    Kanaloa 2201

    Kanaloa 2201

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $239 to $748/night

  27. 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

    $354 to $1,060/night

  28. CONDOMINIUM
     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Kaunakakai, HI

    Pool
    FREE CANCELLATION

    $158 to $191/night

  29. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $295/night

  30. CONDOMINIUM
    Kaleialoha 309

    Kaleialoha 309

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $180 to $361/night

  31. CONDOMINIUM
    Kahana Sunset F6

    Kahana Sunset F6

    Lahiana, HI

    Pool

    $371 to $484/night

  32. CONDOMINIUM
    Mahana At Kaanapali 306

    Mahana At Kaanapali 306

    Lahaina, HI

    Pool Hot Tub

    $236 to $304/night

  33. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $223 to $624/night

  34. CONDOMINIUM
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    Pool

    $581 to $969/night

  35. CONDOMINIUM
    Kahana Sunset F2

    Kahana Sunset F2

    Lahaina, HI

    Pool

    $428 to $484/night

  36. CONDOMINIUM
    Sands Of Kahana 215

    Sands Of Kahana 215

    LAHAINA, HI

    Pool Hot Tub

    $506 to $563/night

  37. CONDOMINIUM
    Kaleialoha #215

    Kaleialoha #215

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $171 to $289/night

  38. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    Pool
    FREE CANCELLATION

    $146 to $466/night

  39. CONDOMINIUM
    Kaleialoha #312

    Kaleialoha #312

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $195 to $313/night

  40. CONDOMINIUM
    Royal Sea Cliff #415

    Royal Sea Cliff #415

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $748/night

  41. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $229 to $282/night

  42. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $484/night

  43. CONDOMINIUM
    Kahana Sunset A4

    Kahana Sunset A4

    Lahaina, HI

    Pool

    $428 to $484/night

  44. CONDOMINIUM
    Sands Of Kahana 234

    Sands Of Kahana 234

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  45. CONDOMINIUM
    Sands Of Kahana 315

    Sands Of Kahana 315

    Lahaina, HI

    Pool Hot Tub

    $506 to $563/night

  46. CONDOMINIUM
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Pool Hot Tub

    $501 to $619/night

  47. CONDOMINIUM
    Royal Kahana 920

    Royal Kahana 920

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $225 to $443/night

  48. CONDOMINIUM
    Lokelani A203

    Lokelani A203

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $313 to $594/night

  49. CONDOMINIUM
    Kaleialoha #304

    Kaleialoha #304

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $207 to $443/night

  50. CONDOMINIUM
    Sea Village 1-203

    Sea Village 1-203

    Kailua-Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $231/night

  51. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    Pool Hot Tub
    FREE CANCELLATION

    $374 to $769/night