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
    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

  2. 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

  3. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Mauna Kea condo descriptionRare 3BR * Sleeps 6 * Panoramic Ocean Views * On 4th Fairway * Amenity Cards Available with fee*Kumulani G-1, our 3-bedroom, 2-bathroom condominium home in the world-famous Mauna Kea Resort, has an Ocean view and also...

    Pool Hot Tub

    $342 to $646/night

  4. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    IS 210-SUMMER Special Prices! Tranquil Oceanfront 1-Bedroom, 1-Bathroom Condo in Maalaea: Maui's Best Kept Secret!We invite you to be our guest in our 1-bedroom, 1-bath oceanfront home.There is an air conditioner in the living room to keep those hot...

    Pool
    FREE CANCELLATION

    $165 to $316/night

  5. HOUSE
    Ho'o Maluhia

    Ho'o Maluhia

    Kailua Kona, HI

    This beautiful home features luxury and artistic touches to add a splash of sophistication to your vacation. The beautiful layout, wood floors and cool tiles fill the house.The master bedroom is located on the upper level. This room includes a...

    Pool

    $444 to $730/night

  6. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Why book individual resorts or condos when your whole group can enjoy a mansion in paradise? Enjoy exceptional panoramic coastal views from the private and quiet custom home at the O’oma Plantation.This large home is the perfect escape for a large...

    Pool Hot Tub

    $1,179 to $1,664/night

  7. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    This stunning Poipu home boasts over 3,300 square feet of elegant living space, along with sweeping views from the coastline up the sloping hills of Kalaheo. An open floor plan provides guests with the perfect setting for quality time together,...

    Pool Hot Tub

    $899 to $2,487/night

  8. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Our well-appointed home has everything you could possible need. Fresh, home grown mango, guava and finger lime for our guests to feast on . Enjoy the relaxing sound of the cascading rush of your private pool's waterfall. The lush golf green views...

    Pool Hot Tub

    $1,917 to $5,992/night

  9. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Indulge yourself in the ultimate island style luxury at the Big Island of Hawaii’s most exclusive retreat, Kauhale Pilialoha. Experience breathtaking sunsets, enjoy the natural beauty of Hawaii from the ultimate poolside lanai perched on the...

    Pool Hot Tub

    $17,975 to $27,561/night

  10. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Relax in your own private pool and waterfall spa on a spacious deck while enjoying some of the best panoramic ocean, coastline, sunset, and Maui views in the entire Mauna Kea Resort. This exquisite luxury property, recently renovated and refreshed...

    Pool Hot Tub

    $1,220 to $3,856/night

  11. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Relax and luxuriate in this spacious and bright four bedroom luxury property, newly renovated, redesigned and brand new to the rental market! Professional and cheerful Fine Design interior decor echoes tones of the nearby Pacific. Unwind on the...

    Pool Hot Tub

    $1,703 to $4,290/night

  12. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Kaleialoha #109This DIRECT oceanfront unit has Queen bed and is fully equipped with all basic amenities. AC in living area! New 55" flat screen in living room and 2nd TV in bedroom. Open and airy living area and open kitchen with recent upgrades...

    Pool
    FREE CANCELLATION

    $183 to $325/night

  13. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Sweeping Ocean Views & Separate Ohana. Rare 4 bedroom - Wai'ula'ula at Mauna Kea.Step into a dream at an exceptional four-bedroom ocean-view rental at Wai'ula'ula within the Mauna Kea Resort.At this single level brand new home, you will find a...

    Pool Hot Tub

    $1,168 to $2,876/night

  14. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This Villa is the owner’s primary residence under section 121 of IRC. The owners offer it for rent during limited periods. As such, it is Exempt from STVR rules, so it has no STVR registration #. TAT is TA-185-465-4464-01 . Villa operates in...

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $762/night

  15. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Thoughtfully designed with your comfort in mind, Hale Nui will exceed your expectations! After a long, arduous flight, each guest will feel embraced upon entering this exquisite, spacious home and everyone will immediately marvel at the panoramic...

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night