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. CONDOMINIUM
    Waipouli Beach Resort G-404

    Waipouli Beach Resort G-404

    Kapaa, HI

    Pool

    $456 to $572/night

  2. CONDOMINIUM
    Waipouli Beach Resort A-404

    Waipouli Beach Resort A-404

    Kapaa, HI

    Pool

    $456 to $572/night

  3. CONDOMINIUM
    Regency at Poipu Kai #721

    Regency at Poipu Kai #721

    Koloa, HI

    Pool

    $363 to $514/night

  4. CONDOMINIUM
    Plantations at Princeville #1122

    Plantations at Princeville #1122

    Princeville, HI

    Pool

    $259 to $311/night

  5. CONDOMINIUM
    Wailea Grand Champion, #154

    Wailea Grand Champion, #154

    Wailea, HI

    Pool

    $297 to $672/night

  6. CONDOMINIUM
    Royal Mauian Unit #315

    Royal Mauian Unit #315

    Kihei, HI

    Pool

    $437 to $605/night

  7. CONDOMINIUM
    Wailea Elua Unit #1002

    Wailea Elua Unit #1002

    Wailea, HI

    Pool

    $762 to $1,515/night

  8. CONDOMINIUM
    Kihei Beach Unit #606

    Kihei Beach Unit #606

    Kihei, HI

    Pool

    $241 to $326/night

  9. CONDOMINIUM
    Wailea Elua #2204

    Wailea Elua #2204

    Wailea, Maui, HI

    Pool

    $724 to $1,065/night

  10. CONDOMINIUM
    Wailea Elua Unit #0702

    Wailea Elua Unit #0702

    Wailea, HI

    Pool

    $459 to $953/night

  11. CONDOMINIUM
    Kihei Beach Unit #501

    Kihei Beach Unit #501

    Kihei, HI

    Pool

    $280 to $448/night

  12. CONDOMINIUM
    Wailea Elua Unit #2304

    Wailea Elua Unit #2304

    Wailea, HI

    Pool

    $724 to $1,065/night

  13. CONDOMINIUM
    Aina Nalu Condo B103

    Aina Nalu Condo B103

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  14. CONDOMINIUM
    Aina Nalu Condo C208

    Aina Nalu Condo C208

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $212 to $618/night

  15. CONDOMINIUM
    Lahaina Condo J209

    Lahaina Condo J209

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $212 to $618/night

  16. CONDOMINIUM
    Lahaina Condo D203

    Lahaina Condo D203

    St. Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  17. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    FREE CANCELLATION

    $485 to $652/night

  18. CONDOMINIUM
    Aina Nalu Premier Condo B108

    Aina Nalu Premier Condo B108

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $217 to $604/night

  19. CONDOMINIUM
    Aina Nalu Premier Condo H110

    Aina Nalu Premier Condo H110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $591/night

  20. 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

  21. HOUSE
    Iki Nui Hale

    Iki Nui Hale

    Princeville, HI

    $464 to $902/night

  22. HOUSE
    Ocean Soul (Big Island)

    Ocean Soul (Big Island)

    Ookala, HI

    Pool

    $530 to $780/night

  23. TOWNHOUSE
    Poipu Crater

    Poipu Crater

    Koloa, HI

    Pool

    $314 to $730/night

  24. HOUSE
    Kiahuna Lani at Poipu

    Kiahuna Lani at Poipu

    Koloa, HI

    Pool Hot Tub

    $542 to $1,421/night

  25. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Pool

    $750 to $1,677/night

  26. ESTATE
    Mauna Kea Bluffs #5: La Ikena O Komohana

    Mauna Kea Bluffs #5: La Ikena O Komohana

    Kamuela, HI

    Pool Hot Tub

    $10,240 to $12,620/night

  27. CONDOMINIUM
    Aina Nalu B106- Extremely Rare Unit

    Aina Nalu B106- Extremely Rare Unit

    Lahaina, HI

    Pool Hot Tub

    $262 to $737/night

  28. 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

  29. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,002 to $4,290/night

  30. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/night