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
    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
    Plantations at Princeville #111

    Plantations at Princeville #111

    Princeville, HI

    Pool

    $253 to $311/night

  4. CONDOMINIUM
    Pali Ke Kua #204

    Pali Ke Kua #204

    Princeville, HI

    Pool

    $270 to $305/night

  5. CONDOMINIUM
    Puu Poa #305

    Puu Poa #305

    Princeville, HI

    Pool

    $334 to $363/night

  6. CONDOMINIUM
    Regency at Poipu Kai #721

    Regency at Poipu Kai #721

    Koloa, HI

    Pool

    $363 to $514/night

  7. CONDOMINIUM
    Plantations at Princeville #1122

    Plantations at Princeville #1122

    Princeville, HI

    Pool

    $259 to $311/night

  8. 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

  9. CONDOMINIUM
    Lahaina Condo D203

    Lahaina Condo D203

    St. Lahaina, HI

    Pool
    FREE CANCELLATION

    $231 to $618/night

  10. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    FREE CANCELLATION

    $485 to $652/night

  11. CONDOMINIUM
    Aina Nalu Premier Condo H110

    Aina Nalu Premier Condo H110

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $205 to $591/night

  12. CONDOMINIUM
    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Unit 903

    Lovely Condo with Pool & Hot Tub! Waikoloa Hills Uni...

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $177 to $225/night

  13. 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

  14. CONDOMINIUM
    Perfect for Your Vacation!- 2 Bed/2 Bath on the Golf Course

    Perfect for Your Vacation!- 2 Bed/2 Bath on the Golf Cou...

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $183/night

  15. HOUSE
    Iki Nui Hale

    Iki Nui Hale

    Princeville, HI

    $464 to $902/night

  16. HOUSE
    Ocean Soul (Big Island)

    Ocean Soul (Big Island)

    Ookala, HI

    Pool

    $530 to $780/night

  17. TOWNHOUSE
    Poipu Crater

    Poipu Crater

    Koloa, HI

    Pool

    $314 to $730/night

  18. COTTAGE
    Honl's Beach Hale (Big Island)

    Honl's Beach Hale (Big Island)

    Kailua Kona, HI

    Hot Tub

    $443 to $1,137/night

  19. HOUSE
    Kiahuna Lani at Poipu

    Kiahuna Lani at Poipu

    Koloa, HI

    Pool Hot Tub

    $542 to $1,421/night

  20. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Pool

    $750 to $1,677/night

  21. HOUSE
    Kahikole

    Kahikole

    Keaau, HI

    $326 to $542/night

  22. HOUSE
    Milo Hae Hale

    Milo Hae Hale

    Koloa, HI

    Pool

    $661 to $1,854/night

  23. 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

  24. CONDOMINIUM
    Aina Nalu B106- Extremely Rare Unit

    Aina Nalu B106- Extremely Rare Unit

    Lahaina, HI

    Pool Hot Tub

    $262 to $737/night

  25. CONDOMINIUM
    Paniolo Hale R2

    Paniolo Hale R2

    Maunaloa, HI

    Pool
    FREE CANCELLATION

    $141 to $169/night

  26. 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

  27. APARTMENT
    Golf Course Views & Private! Lovely Renovated 2 Bed/2 Bath- Elima Lani 207

    Golf Course Views & Private! Lovely Renovated 2 Bed/...

    Waikoloa, HI

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $213/night

  28. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,002 to $4,290/night

  29. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,226 to $3,856/night

  30. CONDOMINIUM
    304 Punahoa Condominium

    304 Punahoa Condominium

    Kihei, HI

    $139 to $287/night