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. HOUSE
    Holoholo ku Waimea

    Holoholo ku Waimea

    Waimea, HI

    HoloHolo Ku is the most charming neighborhood. It's like living in a storybook with huge ranch lands, horses and the view of beautiful Mauna Kea. Walk to town and walk to one of the most famous farmer's markets in Waimea. Minimum 30 Day Rental The...

    FREE CANCELLATION

    $193 to $255/night

  2. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    Hale Kohola “The House of the Whale” is situated on 3 acres in an ideal location on the Kohala Coast, with panoramic views of the ocean and coastline. The master bedroom has a stunning ocean view that you can enjoy by just lifting your head off...

    FREE CANCELLATION

    $347 to $466/night

  3. CONDOMINIUM
    204 Punahoa Condominium

    204 Punahoa Condominium

    Kihei, HI

    Oceanfront studio! Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. Our studios feature a real pull down Queen...

    $114 to $287/night

  4. CONDOMINIUM
    Aina Nalu Condo I210

    Aina Nalu Condo I210

    Lahaina, HI

    We invite you to come and stay in our upgraded condo just two blocks from famous Front Street!  Relax and enjoy Premier 2bd/2ba Aina Nalu condo in Lahaina, Maui.  Corner-end condo with views of the Makai pool area! 846 sq. ft. for spacious living...

    Pool
    FREE CANCELLATION

    $217 to $604/night

  5. CONDOMINIUM
    401 Punahoa Condominium

    401 Punahoa Condominium

    Kihei, HI

    1 bedroom Penthouse unit! Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. "All Units Are Non-smoking"...

    $240 to $411/night

  6. CONDOMINIUM
    302 Punahoa Condominium

    302 Punahoa Condominium

    Kihei, HI

    Oceanfront 1 bedroom condo! Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. "All Units Are Non-smoking"...

    $176 to $382/night

  7. HOUSE
    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    Princeville, HI

    This custom designed home by Hawaii's renowned architect Mark Eyler is located on the idyllic northshore of Kauai. Designed for professional surfer Bruce Irons, the architecture and interior design blends Balinese, Hawaiian and Asian elements with a...

    Pool

    $1,553 to $3,338/night

  8. HOUSE
    Luana Hale

    Luana Hale

    Princeville, HI

    Your Princeville paradise awaits in this luxury single-level home in a quiet neighborhood on the lush north shore of Kauai. Tastefully decorated with fine finishes such as travertine tile and Brazilian cherry flooring, Luana Hale offers over 2,800...

    $512 to $1,032/night

  9. CONDOMINIUM
    Mahina Surf 205 Condo

    Mahina Surf 205 Condo

    Lahaina, HI

    We welcome you to come and enjoy the pristine Pacific Ocean views that warmly greet you from our Mahina Surf 205 lanai.  This unit has a private bedroom, a loft, 2 full bathrooms, a queen sofa sleeper in the living room, and is conveniently cooled...

    Pool
    FREE CANCELLATION

    $274 to $649/night

  10. CONDOMINIUM
    Ilikai Marina Condo 1786 *Legal Vacation Rental

    Ilikai Marina Condo 1786 *Legal Vacation Rental

    Honolulu, HI

    Our LEGALLY ZONED vacation rental is located at Ilikai Marina Condominiums,  1765 Ala Moana Blvd.   If you are looking for a fully equipped unit with 180 degree of ocean and beautiful Hawaiian scenery, then your search is over and you have found...

    FREE CANCELLATION

    $219 to $731/night

  11. CONDOMINIUM
    Lahaina Condo K109

    Lahaina Condo K109

    Lahaina, HI

    We invite you to come and stay in our upgraded condo just two blocks from famous Front Street!  Relax and enjoy Premier Platinum 2bd/2ba Aina Nalu condo in Lahaina, Maui. 846 sq. ft. for spacious living for up to 6 adults (king bed in master...

    Pool
    FREE CANCELLATION

    $231 to $618/night

  12. CONDOMINIUM
    Aina Nalu D-207: Affordable luxury at it's best!

    Aina Nalu D-207: Affordable luxury at it's best!

    Lahaina, HI

    Welcome to Paradise! This home is a 2 bedroom, 2 bath condo on the top floor of Aina Nalu, a centrally located, boutique property in downtown Lahaina. Our guests love the proximity to Lahaina Harbor and the shops/restaurants of Front Street,...

    Pool Hot Tub

    $279 to $1,070/night

  13. CONDOMINIUM
    Lahaina Condo J201

    Lahaina Condo J201

    Lahaina, HI

    We invite you to come and stay in our upgraded condo just two blocks from famous Front Street!  Relax and enjoy Premier Platinum 2bd/2ba Aina Nalu condo in Lahaina, Maui. Corner-end condo with partial views of the West Maui Mountains! 846 sq. ft....

    Pool
    FREE CANCELLATION

    $231 to $618/night

  14. CONDOMINIUM
    Aina Nalu Premier Condo H207

    Aina Nalu Premier Condo H207

    Lahaina, HI

    We invite you to come and stay in our upgraded condo just two blocks from famous Front Street!  Relax and enjoy Premier 2bd/1ba Aina Nalu condo in Lahaina, Maui. 772 sq. ft. for spacious living for up to 6 adults (queen bed in master bedroom,...

    Pool
    FREE CANCELLATION

    $192 to $579/night

  15. APARTMENT
    Nohea Villa

    Nohea Villa

    Princeville, HI

    This villa at Villas of Kamalii, Princeville, is an upscale luxurious and tropically decorated, two bedroom, three bath Villa. Two large en-suite bedrooms, one queen with a shower and one king with jacuzzi tub downstairs, and a third reading room on...

    Pool Hot Tub

    $393 to $863/night

  16. ESTATE
    Hale Kauka

    Hale Kauka

    Kamuela, HI

    ***This property is currently for sale and may be shown during your stay. The property manager will contact you to make arrangements for showings.******Please note there is a 7 night minimum during the holidays. Christmas reservations must check out...

    Pool

    $958 to $1,375/night

  17. CONDOMINIUM
    Aina Nalu Condo A107

    Aina Nalu Condo A107

    Lahaina, HI

    We invite you to come and stay in our upgraded condo just two blocks from famous Front Street!  Relax and enjoy Premier 2bd/2ba Aina Nalu condo in Lahaina, Maui. Located in the Malia building, A107 is by the small pool. View of the pool from the...

    Pool
    FREE CANCELLATION

    $217 to $604/night

  18. CONDOMINIUM
    Kona Mansions A-203

    Kona Mansions A-203

    Kailua Kona, HI

    One-bedroom with expansive ocean views and King bed, located right on the edge of town.This 2nd floor condo features expansive ocean views and spectacular sunsets all year round. The open floor plan has A/C throughout, reliable 60 Mbps Wi-Fi, and...

    Pool

    $232 to $474/night

  19. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Island living at its finest! Experience charming plantation style living in this gorgeous Poipu home. Enjoy all the Robert Trent Jones, Jr. community has to offer conveniently located along the Kiahuna Golf Course. Shopping, golf, and beach...

    Pool Hot Tub

    $780 to $2,199/night

  20. HOUSE
    Keauhou Estates #185

    Keauhou Estates #185

    Kailua Kona, HI

    Experience privacy and panoramic Pacific views just ten minutes from endless dining and shopping options in downtown Kailua-Kona. Situated in the exclusive gated Keauhou Estates community, this elegant custom home features three bedrooms and two...

    Hot Tub

    $482 to $780/night

  21. HOUSE
    Hale Pulelehua with Guest House TVNC#1238

    Hale Pulelehua with Guest House TVNC#1238

    Hanalei, HI

    Summer SPECIAL! 20% off the nightly rate from NOW through October 2019!The Road to Haena is opening! Book now to reserve your summer vacation!TVNC: 1238A classic plantation style home, this Haena beach house, known as Hale Pulelehu'a (The Butterfly...

    $952 to $2,635/night

  22. CONDOMINIUM
    Mauna Lani Fairways #102

    Mauna Lani Fairways #102

    Kamuela, HI

    This beautiful townhome boasts a desirable location nestled in a corner building with open space and distant mountain view just off your private lanai. Only a short stroll from the gorgeous waterfall pool, jacuzzi & fitness center, you won't want to...

    Pool

    $375 to $731/night

  23. CONDOMINIUM
    Aina Nalu Condo H208

    Aina Nalu Condo H208

    Lahaina, HI

    We invite you to come and stay in our upgraded condo just two blocks from famous Front Street!  Relax and enjoy  Premier Platinum 2bd/1ba Aina Nalu condo in Lahaina, Maui. 846 sq. ft. for spacious living for up to 6 adults (queen bed in master...

    Pool
    FREE CANCELLATION

    $205 to $591/night

  24. CONDOMINIUM
    Aina Nalu Premier Platinum C206

    Aina Nalu Premier Platinum C206

    Lahaina, HI

    We invite you to come and stay in our condo just two blocks from famous Front Street!  Relax and enjoy 1 bed / 1 bath Aina Nalu condo in Lahaina, Maui. This condo is located near the Mauka pool and pavilion. 515 sq. ft. for spacious living for up...

    Pool
    FREE CANCELLATION

    $178 to $566/night

  25. CONDOMINIUM
    Kaanapali Royal #A201 (MAUI)

    Kaanapali Royal #A201 (MAUI)

    Lahaina, HI

    FALL SPECIAL! 10% off until the end of November!Experience five-star Maui luxury at an affordable price! This modern ground-floor unit at Kaanapali Royal features a spacious floor plan that opens to sweeping golf course views. Extensively remodeled...

    Pool Hot Tub

    $393 to $1,336/night

  26. HOUSE
    Paradise Bluff

    Paradise Bluff

    Laupahoehoe, HI

    *Published rates are for double occupancy. Extra guests up to a total of six are charged $25 per night. All guests must be registered, Mahalo!Paradise Bluff is a beautiful home perched on the cliffs of the small seaside town of Laupahoehoe. Relax,...

    Pool

    $417 to $906/night

  27. HOUSE
    Kiahuna Plantation Hale

    Kiahuna Plantation Hale

    Koloa, HI

    Enjoy the ultimate Poipu vacation experience at Kiahuna Plantation Hale, located on the fourth fairway of the Kiahuna Plantation Golf Course in lovely Wainani at Poipu. This stunning home boasts gorgeous mountain views, a split air conditioning...

    Pool Hot Tub

    $542 to $1,508/night

  28. HOUSE
    Hale Anu Keanu

    Hale Anu Keanu

    Princeville, HI

    With an ideal location, plenty of privacy, and a backyard jacuzzi, this newly remodeled, plantation-style vacation home on Kauai's north shore allows you to experience the perfect balance of relaxation and adventure. Meaning “house of cool...

    Hot Tub

    $631 to $1,693/night

  29. CONDOMINIUM
    Waikiki Grand 516 Condo

    Waikiki Grand 516 Condo

    Honolulu, HI

     Legally permitted vacation rental -  134 Kapahulu Ave  #516 Studio w/ Queen Size Bed, Full Bath & Kitchenette This is actually one of my favorite suites at the Waikiki Grand, not only for the price but the comfort level. I think the kitchen...

    Pool
    FREE CANCELLATION

    $133 to $179/night

  30. HOUSE
    Holua Kai #34

    Holua Kai #34

    Kailua Kona, HI

    Situated in the exclusive, gated oceanfront community of Holua Kai, this luxurious and inviting home provides the perfect setting for your Hawaiian getaway. The home comfortably accommodates six and is just a 10-minute walk from Keauhou Bay, the...

    Pool

    $423 to $839/night