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. $347 to $466/night

    Hale Kohola

    Hale Kohola

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  2. $193 to $255/night

    Holoholo ku Waimea

    Holoholo ku Waimea

    3 BedroomsBathroomsSleeps 6
    14 nights minstay
    FREE CANCELLATION
  3. $197 to $292/night

    Keauhou Kona Surf & Racquet Club#7-102 "Honu Hale"

    Keauhou Kona Surf & Racquet Club#7-102 "Honu Ha...

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  4. $342 to $646/night

    Hale Kaimana

    Hale Kaimana

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  5. $164 to $502/night

    Kaleialoha #312

    Kaleialoha #312

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  6. $176 to $502/night

    Kaleialoha #304

    Kaleialoha #304

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  7. $661 to $1,910/night

    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  8. $164 to $231/night

    Sea Village 1-203

    Sea Village 1-203

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  9. $471 to $683/night

    Hale Ke Aluala

    Hale Ke Aluala

    2 Bedrooms BathroomSleeps 6
    5 nights minstay
    FREE CANCELLATION
  10. $899 to $2,681/night

    Mana Alana at Poipu

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  11. $542 to $1,330/night

    Awapuhi Hale

    Awapuhi Hale

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  12. $17,975 to $27,561/night

    Kauhale Pilialoha

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    5 nights minstay
    Pool Hot Tub
  13. $1,102 to $3,791/night

    3BD Fairways Villa (116D) at Four Seasons Resort Hualalai

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  14. $164 to $502/night

    Kaleialoha #315

    Kaleialoha #315

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  15. $219 to $280/night

    OTA House

    OTA House

    2 Bedrooms1.5  BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  16. $800 to $2,616/night

    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  17. $152 to $443/night

    Kaleialoha #109

    Kaleialoha #109

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. $1,165 to $3,966/night

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  19. $581 to $969/night

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  20. $314 to $764/night

    Poipu Crater

    Poipu Crater

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  21. $1,261 to $4,648/night

    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  22. $2,203 to $4,290/night

    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  23. $1,168 to $2,876/night

    Hale Keanu

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  24. $478 to $1,673/night

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  25. $1,938 to $4,750/night

    Hale Nui

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION