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Hawaii Vacation Rentals - 2389 Properties

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. Sleeps 6, $199 to $341/night

    City : Waimea
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Step into this sunny and bright condo located directly across the...

  2. Sleeps 10, $2838 to $4540/night

    City : Kailua-Kona
    Bedrooms : 3
    Bathrooms : 4
    Pool

    Perfectly located on the Kona “Gold Coast” of the Big Island...

  3. Sleeps 3, $269 to $319/night

    City : Lahaina
    Bedroom : studio
    Bathroom : 1
    Pool Hot Tub

    {Jr. Suite (Studio)- King bed; Flat screen TV; extended lanai} MAUI...

  4. Sleeps 5, $359 to $419/night

    City : Kaanapali
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    Our One Bedroom Corner unit is spacious and well-appointed with a...

  5. Sleeps 2, $157 to $244/night

    City : Honolulu
    Bedroom : studio
    Bathroom : 1
    Pool Hot Tub

    Island Colony is located in the heart of Waikiki. Close to...

  6. Sleeps 3, $179 to $271/night

    City : Honolulu
    Bedroom : studio
    Bathroom : 1
    Pool Hot Tub

    Island Colony is located in the heart of Waikiki. Close to...

  7. Sleeps 4, $212 to $320/night

    City : Honolulu
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    The Waikiki Banyan is a very popular, moderately priced family...

  8. Sleeps 6, $224 to $284/night

    City : Waimea
    Bedrooms : 3
    Bathrooms : 2

    Tastefully designed by the Owners to create a carefree island...

  9. Sleeps 4, $231 to $550/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Kamaole Sands is one of the most “resort like” condominium...

  10. Sleeps 4, $221 to $267/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool Hot Tub

    Relax and kick off your shoes in this Polynesian decorated top floor...

  11. Sleeps 6, $284 to $358/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool Hot Tub

    This spacious two bedroom vacation rental is the perfect home away...

  12. Sleeps 6, $284 to $454/night

    City : Princeville
    Bedrooms : 3
    Bathrooms : 3
    Pool Hot Tub

    Dream. Believe. Discover. These are the words imprinted on several...

  13. Sleeps 6, $341 to $448/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Pu’u Po’a 102 is located on the bluff of Princeville with...

  14. Sleeps 4, $341 to $448/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This deluxe Kauai vacation rental is sure to take your breath away...

  15. Sleeps 4, $221 to $284/night

    City : Princeville
    Bedroom : 1
    Bathroom : 1
    Pool

    Sealodge is located on Kauai’s most spectacular coastline,...

  16. Sleeps 8, $221 to $250/night

    City : Princeville
    Bedrooms : 2
    Bathrooms : 2
    Pool Hot Tub

    This new Plantation at Princeville located on the north shore is...

  17. Sleeps 6, $235 to $603/night

    City : Lahaina
    Bedrooms : 2
    Bathrooms : 2
    Pool

    We invite you to come and stay in our upgraded condo just two blocks...

  18. Sleeps 6, $211 to $578/night

    City : Lahaina
    Bedrooms : 2
    Bathrooms : 2
    Pool

    We invite you to come and stay in our upgraded condo just two blocks...

  19. Sleeps 6, $211 to $578/night

    City : Lahaina
    Bedrooms : 2
    Bathrooms : 2
    Pool

    We invite you to come and stay in our upgraded condo just two blocks...

  20. Sleeps 4, $155 to $518/night

    City : Lahaina
    Bedroom : 1
    Bathroom : 1
    Pool

    We invite you to come and stay in our upgraded condo just two blocks...

  21. Sleeps 4, $179 to $271/night

    City : Honolulu
    Bedroom : studio
    Bathroom : 1
    Pool

    Island Colony is located in the heart of Waikiki. It is close to...

  22. Sleeps 2, $240 to $297/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    This one bedroom garden and mountain view condo sleeps up to 2...

  23. Sleeps 4, $368 to $445/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

    You will not be disappointed! This well-appointed two bedroom garden...

  24. Sleeps 4, $258 to $312/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Tropical decor and furnishings create a relaxing setting in this...

  25. Sleeps 4, $244 to $297/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Spacious and comfortable describe this ground floor condo with a...

  26. Sleeps 6, $312 to $391/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Ocean View condo located on the ground floor next to the pool. This...

  27. Sleeps 4, $273 to $327/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Enjoy beautiful Ocean Views as well as views of the center court...

  28. Sleeps 4, $297 to $373/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Enjoy Ocean Views from the living room and master bedroom in this...

  29. Sleeps 4, $273 to $327/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Enjoy Ocean Views from this one (1) bedroom Condo. This unit has a...

  30. Sleeps 2, $259 to $312/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Newly Renovated One bedroom Ocean View Condo. This unit has been...