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
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Book today and Fall in LOVE with "HiiLani" (In the arms of Heaven)... You will feel like you have gone back in time to the true Hawaiian experience in this condo just 15 FT from the water's edge! 204 Pohailani Welcomes you with so much ALOHA.....

    Pool
    FREE CANCELLATION

    $199 to $264/night

  2. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    Book today and Fall in LOVE with "THE LIL GRASS SHACK" You will feel like you have gone back in time to the true Hawaiian experience in this condo, just 10 FT from the water's edge! 103 Pohailani Welcomes you with so much Included in our...

    FREE CANCELLATION

    $187 to $239/night

  3. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $717 to $1,784/night

  4. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Enjoy unbeatable panoramic views from this highly desirable 6th floor oceanfront unit on the Kaanapali coast. You can’t get any closer to the ocean than this resort! Watch gorgeous sunsets over Molokai and Lanai every day from the comfort of your...

    Pool Hot Tub
    FREE CANCELLATION

    $189 to $630/night

  5. TOWNHOUSE
    Puamana 24-3

    Puamana 24-3

    Lahaina, HI

    This bright 1 bedroom, 2 bath "Beach House "has an ideal location in Puamana on quiet Puamelia Place, steps to the beach access or the footbridge leading to the Club house. It even has a peek of the ocean.This Maui vacation rental has a very...

    Pool
    FREE CANCELLATION

    $209 to $700/night

  6. CONDOMINIUM
    Napili Shores D127

    Napili Shores D127

    Lahaina, HI

    Ready for an unforgettable getaway? Come see what Napili has to offer! This spacious studio unit with a King bed and pull-out sofa sleeps 3 and offers AC, wifi, cable, a DVD player, and it's own walk-out lanai! Mix up some drinks and walk the...

    Pool Hot Tub
    FREE CANCELLATION

    $139 to $539/night

  7. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    ~Book today and Fall in LOVE with "THE HULA HIDEAWAY" You will feel like you have gone back in time to the true Hawaiian experience in this condo just 10 FT from the water's edge! 303 Hula Hideaway Welcomes you with so much Some of the many...

    Pool
    FREE CANCELLATION

    $229 to $282/night

  8. CONDOMINIUM
    Valley Isle 110

    Valley Isle 110

    Lahaina, HI

    ~Book today and Fall in LOVE with 110 Valley iIsle The"Aloha House" You will feel like you have gone back in time to the true Hawaiian experience in this condo just STEPS from the water's edge! 110 Valley Isle Welcomes you with so much Some of...

    Pool
    FREE CANCELLATION

    $235 to $312/night

  9. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Relax and enjoy Maui from this adorable 1bd/1ba condo! This unit offers all the comforts of home with WiFi, Cable, DVD Player, and Central AC. You'll also get to enjoy the fully-stocked kitchen, on-site laundry room, and private ocean-view and...

    Pool Hot Tub
    FREE CANCELLATION

    $130 to $548/night

  10. CONDOMINIUM
    Napili Shores B214

    Napili Shores B214

    Lahaina, HI

    This amazing property offers a fully equipped kitchen and with a new hide-away queen bed, a sofa, and hide-away twin bunk beds, this unit sleeps up to 5 guests. You just can't find another property like this one, both value and location. Located...

    Pool Hot Tub
    FREE CANCELLATION

    $200 to $650/night

  11. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    This brand-new beautiful new 5th floor listing at the Mahana at Kaanapali boasts gorgeous views of both the tranquil blue Pacific Ocean AND the lush West Maui Mountains. This property is extremely close to the water, you can literally sit in the 5th...

    Pool Hot Tub
    FREE CANCELLATION

    $499 to $1,751/night

  12. CONDOMINIUM
    Wailea Ekahi 36C

    Wailea Ekahi 36C

    Wailea, HI

    Gorgeous 1 bedroom unit at the world-renowned Wailea Ekahi Village, located on Keawakapu Beach! This unit has one King Bed and one sleeper sofa, accommodating up to 4 guests. With hardwood floors, a well-stocked kitchen, cable, wifi, a washer/dryer,...

    Pool
    FREE CANCELLATION

    $188 to $645/night

  13. CONDOMINIUM
    Paki Maui 123

    Paki Maui 123

    LAHAINA, HI

    Located in the front of the building, as close to the pool and ocean as you can get. At over 1200 sq feet, there is enough room to bring the whole family. Sleep 6 comfortably in our 2 bedroom 2 bath unit with full kitchen. The ocean front master...

    Pool Hot Tub
    FREE CANCELLATION

    $236 to $815/night

  14. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Enjoy your Maui vacation from the Hale Mahina Resort! This gorgeous 2 bedroom, 2 bath, lush ocean view condo is the perfect place for couples or families looking to experience and explore the island. Equipped with a full kitchen with stainless...

    Pool Hot Tub
    FREE CANCELLATION

    $331 to $686/night

  15. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 437 Welcomes you with SO Much This spacious studio, 1 bath can accommodate up to 4 guests. Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) • Beach umbrella • Beach...

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $413/night

  16. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Come stay and relax at this NEWLY RENOVATED 1bd/1ba condo. This unit offers all the comforts of home with its WiFi, Cable, DVD Player, AC in the living room, and Ceiling Fans throughout. You'll also get to enjoy the fully-stocked kitchen, on-site...

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $529/night

  17. CONDOMINIUM
    Maalaea Banyans 408

    Maalaea Banyans 408

    Wailuku, HI

    Get ready for Paradise! This 3bd/2ba unit sleeps 6 and truly has an unbeatable view. Located in Maalaea, you'll be right by Haycraft Beach Park, the harbor, restaurants, shops, the aquatic center, mini golf, and so much more! You're also in the...

    Pool Hot Tub
    FREE CANCELLATION

    $295 to $800/night

  18. CONDOMINIUM
    Kaleialoha 203

    Kaleialoha 203

    Lahaina, HI

    Come stay with us at the beautiful Kaleialoha Oceanfront Resort!! This spacious One Bedroom one Bath condominium has all of the comforts of home. It's the perfect place for an active family vacation or a couple looking for a romantic getaway. The...

    Pool
    FREE CANCELLATION

    $174 to $613/night

  19. CONDOMINIUM
    Oceanfront 3BR w/ Private Beach & AC

    Oceanfront 3BR w/ Private Beach & AC

    Kihei, HI

    Feel Pacific breezes as you unwind on the lanai of your fourth-floor 3BR/2BA condo. This unit commands the most sought-after location in the building (front and center), closest to the ocean and furthest from the road.Take in stunning wide-open...

    Pool
    FREE CANCELLATION

    $577 to $794/night