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. $364 to $1,219/night

    Honua Kai 520

    Honua Kai 520

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  2. $283 to $1,063/night

    Honua Kai 346

    Honua Kai 346

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  3. $1,791 to $5,992/night

    Hale Waiulu

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  4. $299 to $452/night

    Waipouli Beach Resort C-105

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  5. $456 to $652/night

    Waipouli Beach Resort G-306

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  6. $258 to $506/night

    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  7. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  8. $625 to $1,653/night

    Kolea 6B at the Waikoloa Beach Resort

    Kolea 6B at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $128 to $451/night

    Fairway Villas D2 at the Waikoloa Beach Resort

    Fairway Villas D2 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  10. $456 to $572/night

    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  11. $280 to $426/night

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath Condo

    Close to the Beaches & Shopping! Lovely 3 Bed/2 Bath...

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. $425 to $729/night

    Happy Leilani Hale

    Happy Leilani Hale

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  13. $175 to $614/night

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

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

    3 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. $174 to $445/night

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

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

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  15. $375 to $459/night

    Pali Ke Kua #103

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
  16. $234 to $464/night

    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  17. $618 to $1,236/night

    Wai'ula'ula A102

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  18. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  19. $160 to $466/night

    Fairway Villas D5 at the Waikoloa Beach Resort

    Fairway Villas D5 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. $250 to $536/night

    Fairway Villas I33 at the Waikoloa Beach Resort

    Fairway Villas I33 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  21. $194 to $650/night

    Mauna Lani Fairways #403

    Mauna Lani Fairways #403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. $164 to $231/night

    Sea Village 1-203

    Sea Village 1-203

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  23. $177 to $448/night

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  24. $322 to $430/night

    Waipouli Beach Resort E-406

    Waipouli Beach Resort E-406

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  25. $259 to $361/night

    Plantations at Princeville #521

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  26. $766 to $846/night

    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  27. $342 to $646/night

    Hale Kaimana

    Hale Kaimana

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  28. $234 to $464/night

    Colony Villas at Waikoloa Beach Resort #2204

    Colony Villas at Waikoloa Beach Resort #2204

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  29. $270 to $791/night

    Palm Villa I3 at the Mauna Lani Resort

    Palm Villa I3 at the Mauna Lani Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. $215 to $630/night

    Fairway Villas M3 at the Waikoloa Beach Resort

    Fairway Villas M3 at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  31. $164 to $480/night

    Beach Villas M3

    Beach Villas M3

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. $464 to $1,355/night

    Kolea 7B at the Waikoloa Beach Resort

    Kolea 7B at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  33. $234 to $464/night

    Waikoloa Beach Villas E32

    Waikoloa Beach Villas E32

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION