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:


Close Filters
  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
    Diamond Head Beach Hotel 501

    Diamond Head Beach Hotel 501

    Honolulu, HI

    This comfortble 2 Bedroom suite offers fabulous Ocean front Lanai and Garden Suite 501 at The Diamond Head Beach Hotel My place is close to Ocean Front at Diamond Head Beach Hotel - Gold Coast Waikiki. You’ll love my place because of Large Ocean...

    Pool
    FREE CANCELLATION

    $298 to $495/night

  4. CONDOMINIUM
    Diamond Head Beach Hotel 602

    Diamond Head Beach Hotel 602

    Honolulu, HI

    Best Location and price on this spacious 1 bedroom suite with full kitchen. A delightful one bedroom apartment at the iconic Diamond Head Beach Hotel on Oahu's Gold Coast the quietest area of Waikiki, loved by many for it s close proximity to the...

    FREE CANCELLATION

    $186 to $309/night

  5. CONDOMINIUM
    Diamond Head Beach Hotel 601

    Diamond Head Beach Hotel 601

    Honolulu, HI

    This oversized 1 Bedroom suite offers fabulous Ocean front Lanai and Garden Our place is spacious, great for two couples or families with kids. Marble counter tops within the full well equipped kitchen (full size fridge freezer and dishwasher) and...

    FREE CANCELLATION

    $298 to $444/night

  6. CONDOMINIUM
    PentHouse 701

    PentHouse 701

    Lahaina, HI

    Kahana Manor Penthouse~Experience "roof top" living at this unique rental. This space is like no other on Maui~ Our Penthouse sits atop the Kahana Manor with a floor of it'sAcross the street from the ocean and above the small town of Kahana you can...

    Pool
    FREE CANCELLATION

    $204 to $370/night

  7. CONDOMINIUM
    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua, HI

    $500K renovation! New pics on the way!!! Completed March 2019! Highend stainless appliances, newly renovated kitchen and baths, new furnishings throughout; new A/C system!Relax and rejuvenate. The warm tropical breezes and soothing sounds of the...

    $781 to $1,219/night

  8. CONDOMINIUM
    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua, HI

    Located in the most desirable area of the resort, (building 21), this beach front 1 bed 1.5 bath villa is just steps from the white sand beach of Oneloa Bay, and a short walk to Kapalua Bay, this little jewel offers expansive ocean views from every...

    Pool

    $625 to $844/night

  9. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    The name 'Kapa' 'lua' means above waters edge. This ocean front beauty is uniquely perched above the waters edge along the most desirable stretch of Maui coastline just steps from the sand. Quiet coves make for excellent snorkeling and swimming,...

    Pool

    $625 to $844/night

  10. HOUSE
    1 Bedroom Corner Oceanfront #808

    1 Bedroom Corner Oceanfront #808

    Lahaina, HI

    Maui Kai unit #808 is a one Bedroom Corner - King bed; Flat screen TV; queen sofa sleeper; TV in bedroom. Beautiful one bedroom corner condo. The ocean front location with its view of the water from our eighth floor lanai is very much like a cruise...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  11. CONDOMINIUM
    Kona Plaza 217

    Kona Plaza 217

    Kailua Kona, HI

    Don’t miss this fabulously updated Kona Plaza vacation rental. Condo #217 is newly available as of January 2019. It's amazing location right in the heart of Historic Kailua Kona Town makes this condo by far one of the most desirable condos...

    Pool
    FREE CANCELLATION

    $229 to $409/night

  12. CONDOMINIUM
    Kaleialoha #215

    Kaleialoha #215

    Lahaina, HI

    Nice corner unit offers privacy and expanded views. Cal King bed, New carpet and appliances. AC, washer/dryer, free wireless internet, local phone and basic cable.Flat screen TV. All basic amenities included including linens, beach supplies and...

    Pool
    FREE CANCELLATION

    $183 to $325/night

  13. CONDOMINIUM
    Eldorado J109

    Eldorado J109

    Lahaina, HI

    The weather is ideal in Maui year round. MAUI ELDORADO HAS THE ONLY PRIVATE BEACH CABANA ON KAANAPALI BEACH FOR MAUI ELDORADO GUESTS ONLY. Experience Maui Eldorado in the Heart of Kaanapali - an affordable vacation in paradise. Maui Eldorado is...

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $299/night

  14. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 508 Welcomes you...This spacious one bedroom one bath plus den can accommodate up to six (6) guests …Included in our fabulous price are many owner-supplied extras such as:• Beach chairs (2)• Beach umbrella•...

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $608/night

  15. CONDOMINIUM
    Kulakane 306

    Kulakane 306

    Lahaina, HI

    This direct oceanfront condo is just 50 feet from the ocean, with unobstructed ocean views from the living room, lanai, kitchen and the mater bed room. Access gates lead you to the very private sandy/rock beach where you can enjoy snorkeling with...

    Pool
    FREE CANCELLATION

    $281 to $311/night

  16. TOWNHOUSE
    Puamana 25-4

    Puamana 25-4

    Lahaina, HI

    Watch breathtaking sunset at the edge of the water surrounded by the beautiful grounds. With a king size bed in the master bedroom, a queen sofa sleeper you can comfortably house 4 people. There is a fully equipped kitchen with dinner & cookware....

    Pool
    FREE CANCELLATION

    $219 to $249/night

  17. CONDOMINIUM
    Waikiki Grand 411

    Waikiki Grand 411

    Honolulu, HI

    Legally permitted vacation rental -  134 Kapahulu Ave  #411 A Sweet Freshly Remodeled & updated balcony Studio Suite next to Waikiki Beach Great View & Balcony. Recently remodeled, painted and upgraded as of November 2018 - park, zoo and ocean...

    Pool
    FREE CANCELLATION

    $124 to $174/night

  18. HOUSE
    Junior Suite Oceanfront #303

    Junior Suite Oceanfront #303

    Lahaina, HI

    Jr. Suite - Bright and Easy Island Style. Queen bed (no sofa bed), tiled entryway, Flat Screen TV, light furnishings throughout. Put away your groceries and make yourself at home. Enjoy your private lanai with your favorite beverage. Watch the...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  19. HOUSE
    Junior Suite Oceanfront #706

    Junior Suite Oceanfront #706

    Kaanapali, HI

    Our Junior Suite is spacious and well-appointed with a Queen Bed; as well as a sofa bed for the occasional guest. There are seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and personal items. The...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  20. CONDOMINIUM
    Casa De Emdeko 330

    Casa De Emdeko 330

    Kailua Kona, HI

    ***COMPLETE REMODEL COMPLETED JANUARY 2016 IN CONDO! Owners have extensively updated the condo from top to bottom.Flooring, Bathroom, Kitchen, Furniture, Lanai all updated! Be one of the first guests to enjoy this renovation!TAKE A VIRTUAL TOUR OF...

    Pool
    FREE CANCELLATION

    $239/night

  21. HOUSE
    Heeia Bay Hale

    Heeia Bay Hale

    Kailua Kona, HI

    Welcome to the listing page of Heeia Bay Hale! A Brand New Vacation Rental as of October 2018. This wonderful 2 story home in Keauhou is WALKING DISTANCE TO HEEIA BAY!!This private & spacious 3 bedroom, 3.25 bath multi-level Hawaiian style beach...

    Pool
    FREE CANCELLATION

    $478 to $772/night

  22. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Welcome to Hale Lani! This gorgeous house is a BRAND NEW VACATION RENTAL that Knutson & Associates Management is proud to represent. Hale Lani is the perfect spot to host a unforgettable Hawaii Vacation. With 4 bedrooms, and a capacity to sleep 14,...

    Pool
    FREE CANCELLATION

    $1,142 to $1,533/night

  23. CONDOMINIUM
    Kaleialoha #208

    Kaleialoha #208

    Lahaina, HI

    Near Shopping, Restaurants and all beach activities. Farmer's Market, coffee shop and beach park 3 blks away. Swim and snorkel right in front of property within our protected outer reef. Observe a myriad of sea life including, sea turtles, dolphins...

    Pool
    FREE CANCELLATION

    $207 to $384/night

  24. HOUSE
    Koana Breeze

    Koana Breeze

    Kailua Kona, HI

    This spectacular 2500 square-foot plantation-style home is perched on a hillside with breathtaking ocean views of Keauhou and Kailua Bays. Enjoy year-round outside dining with fabulous views of gorgeous Kona sunsets on the lanai, and enjoy drinks in...

    Hot Tub
    FREE CANCELLATION

    $513 to $584/night

  25. HOUSE
    Junior Suite Oceanfront #707

    Junior Suite Oceanfront #707

    Kaanapali, HI

    Our 7th floor Junior Suite is spacious and well-appointed with a Queen Bed; as well as a queen sofa sleeper for the occasional guest. There are seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $309/night

  26. CONDOMINIUM
    Royal Kahana 220 (2bd / 2ba)

    Royal Kahana 220 (2bd / 2ba)

    Lahaina, HI

    Ocean front Royal Kahana Resort in West Maui is located in Kahana and offers all the amenities you could possibly want while on a tropical vacation. Our beautiful two bedroom 2 bathroom second floor suite has an ocean view so you can watch the...

    Pool
    FREE CANCELLATION

    $256 to $379/night

  27. CONDOMINIUM
    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    Lahaina, HI

    The ultimate in luxury awaits at our completely remodeled and refurnished 1 bedroom, 1 bathroom oceanfront condo. Just steps from the water, this truly exceptional suite offers spectacular unobstructed ocean and sunset views from the lanai and...

    Pool
    FREE CANCELLATION

    $251 to $346/night

  28. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    MAUNA LANI TERRACE#D-201 Beachfront Location, Breathtaking Views, BEST VALUE!!!!AMAZING NEW PROPERTY BOOKING SPECIALS FOR LAST MINUTE VACANCIES!!Call/Text Blake Kessner, Property Manager at or email for any questions at all!!To get the BEST...

    Pool Hot Tub
    FREE CANCELLATION

    $706 to $759/night

  29. CONDOMINIUM
    Kolepa Aloha

    Kolepa Aloha

    Waikoloa, HI

    Description :Views of Mauna Kea and emerald fairways are yours at this two-bedroom, two-bath vacation rental at Fairway Villas, located within the prestigious Waikoloa Beach Resort. Step onto your private, covered lanai with the day's first cup of...

    Pool Hot Tub

    $162 to $401/night

  30. CONDOMINIUM
    Melemele Pua

    Melemele Pua

    Waikoloa, HI

    Melemele Pau villa a spacious 3 bedroom single level floor plan which incorporates an elegant tropical feel. This stunning, well-appointed end unit is surrounded by a tropical wonderland of exotic gardens & calming unobstructed ocean views on the...

    Pool

    $310 to $605/night