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
    Kaanapali Shores 527

    Kaanapali Shores 527

    Lahaina, HI

    Relax on our 5th floor lanai, overlooking the ocean, well-kept grounds and pool at Kaanapali Shores! Kaanapali Shores resort is located on the beach in North Kaanapali. Unit 527 lanai has views of the ocean, renovated garden pool and spa,...

    Pool Hot Tub
    FREE CANCELLATION

    $311 to $781/night

  2. CONDOMINIUM
    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    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

    $926 to $2,016/night

  3. CONDOMINIUM
    Casa De Emdeko 338

    Casa De Emdeko 338

    Kailua-Kona, HI

    Casa De Emdeko, an oceanfront condominium complex, is located on famous Alii Drive just 1.5 miles south of Kailua Kona Village. This is a no-smoking property. Hale Makana O Ke Akua (Casa de Emdeko 338), "House of Gods Gifts", a two bedroom, two...

    Pool Hot Tub

    $251 to $409/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...

    Pool
    FREE CANCELLATION

    $163 to $366/night

  5. 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

  6. 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

  7. 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...

    Pool Hot Tub
    FREE CANCELLATION

    $299 to $608/night

  8. CONDOMINIUM
    Kaanapali Shores 725

    Kaanapali Shores 725

    Lahaina, HI

    Wonderful ocean and garden views from this spacious 2 bedroom unit . The owners have completed a beautiful remodel featuring carpeting, kitchen and bath upgrades and new furniture. The full kitchen was recently re-done with new appliances, granite...

    Pool Hot Tub
    FREE CANCELLATION

    $359 to $893/night

  9. 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

  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
    Hale Ono Loa 416

    Hale Ono Loa 416

    Lahaina, HI

    This beach house is furnished comfortably in an uncluttered "island style,". Spacious condo, one bedroom and one bath. Well organized Kitchen. High Definition TV, High Speed Internet. Swim, snorkel, 30 seconds away. Reef-protected, p/t...

    Pool
    FREE CANCELLATION

    $174 to $606/night

  13. CONDOMINIUM
    Hale Mahina A-403

    Hale Mahina A-403

    Lahaina, HI

    This two-bedroom, two bath has an open floor plan and gives it the feeling of a penthouse. Living room and kitchen are sunken with a large spacious deck; totally unobstructed view of the beach and ocean. The upstairs bedroom is a large loft that...

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $369/night

  14. CONDOMINIUM
    Paniolo Hale R2

    Paniolo Hale R2

    Maunaloa, HI

    This is a lovely one bedroom, 2 bath condo with open beam ceilings and hardwood floors. Ground floor level has a treetop view living area with a large screened lanai, kitchen,full bath, and dining/living room with flat screen TV/VCR, high speed...

    Pool
    FREE CANCELLATION

    $141 to $169/night

  15. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Enjoy our tropical paradise – Feel tension melt away when take your first look from our unit and see an unobstructed, breath-taking views of Lana'i, Molokai'i and the vast expanse of ocean. It is magnificent at all times of day. Relax to the...

    Pool
    FREE CANCELLATION

    $178 to $263/night

  16. 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

  17. CONDOMINIUM
    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    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 not reserved and can...

    Pool Hot Tub

    $485 to $1,204/night

  18. COTTAGE
    The Cottage

    The Cottage

    Kailua-Kona, HI

    "The Cottage", Mahina Meli Makai (Oceanside Honey Moon) This truly oceanfront Cottage, captures spectacular coastline views as well as the captivating ocean right in front of you. The "Honeymoon Getaway" begins the moment you arrive and step...

    $239 to $379/night

  19. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    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

    $833 to $2,016/night

  20. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    The condo is totally renovated and updated. From your private lanai you have a lovely area to sit and dine or just relax with nothing but the crystal blue ocean and the famous Maui sunsets in front, FRONT SEAT WHALE WATCHING from the lanai. Tile...

    Pool Hot Tub
    FREE CANCELLATION

    $253 to $844/night

  21. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    SUMMER Special Prices! Ocean front studio with ocean views and central A/C to enjoy those hot summer days. Ready for an unforgettable vacation to Maui? Or is it time to just getaway for the weekend? This studio with a beautiful ocean view is the...

    Pool Hot Tub
    FREE CANCELLATION

    $166 to $373/night

  22. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    A beautifully updated kitchen allows for cooking family meals in, saving money for activities and adventures. In addition to the flat screen TV and dvd player in the living room, there is also a TV in the bedroom.. Bring your electronic equipment...

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $700/night

  23. 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

  24. CONDOMINIUM
    Hoyochi Nikko #201

    Hoyochi Nikko #201

    Lahaina, HI

    One bedroom with high vaulted ceilings (additional sleeping capacity on sofa bed in living room). Brand new memory foam mattress. This unit has air conditioning in the bedroom along with a comfortable queen size bed. This condo is fully equipped...

    Pool
    FREE CANCELLATION

    $218 to $369/night

  25. 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

  26. 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

  27. 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

  28. 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

  29. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Nohonani 300 has recently completed a brand new renovation. Improvements include new carpeting and beautiful furnishings. This is an end unit on the third floor giving added privacy and a spectacular crows nest view of the outer islands and golden...

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $403/night

  30. 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