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:


Filter resultsGo Reset filtersReset Close
  1. HOUSE
    Happy Leilani Hale

    Happy Leilani Hale

    Kailua Kona, HI

    Tucked into the side of the mountain just above Kona at a cooler 600 ft. elevationHappy Leilani Hale has a zen feel to it as you look out over the blue pacific and feel theSoft ocean breezes take you away from it all.Enter through the Asian...

    Pool Hot Tub
    FREE CANCELLATION

    $425 to $729/night

  2. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Beautifully appointed "like new" 2 bedroom 2.5 bath oceanfront home with pool. Gourmet kitchen and huge deck for tanning, dining & sunset cocktails. Upstairs master has shower & hot tub. Sliding doors disappear into walls for the ultimate "on the...

    Pool
    FREE CANCELLATION

    $486 to $608/night

  3. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Not one, but two oceanfront pools and a Jacuzzi, what more can you ask for? Unit 110 is a ground floor unit with washer and dryer. New kitchen cabinets and counter tops. You'll love to just walking out from your private lanai right into the...

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $437/night

  4. CONDOMINIUM
    Kaanapali Shores 941

    Kaanapali Shores 941

    Lahaina, HI

    KS 941-SUMMER SPECIALS! Last Minute Summer Prices! Beautifully Remodeled Ocean Front Penthouse w A/CThis 9th floor condo has a spanning view of this beautiful resort you can’t beat the view from the comfort of your lanai. Spacious Living Room...

    Pool
    FREE CANCELLATION

    $171 to $469/night

  5. 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
    FREE CANCELLATION

    $156 to $373/night

  6. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    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 CALENDARIf the calendar shows as available, the Villa is not reserved and can be...

    Pool Hot Tub

    $845 to $1,668/night

  7. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Direct Ocean Front Cottage where you can watch whales and surfers while relaxing on the large sunning deck, literally hanging over the oceans edge. Features two master suites and private pool, and located just 5 miles from Kailua Village at 78-6658...

    Pool
    FREE CANCELLATION

    $432 to $934/night

  8. 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

  9. 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
    FREE CANCELLATION

    $161 to $403/night

  10. 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 $384/night

  11. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Your dream Maui vacation awaits! Kamaole Sands 8-203 is on the second floor of building 8 in one of the most sought-after complexes in South Maui. This unit has been newly updated and has a brand new sofa sleeper in the living area and King mattress...

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $374/night

  12. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    This vintage Hawaiian beach house is nestled in a private gated community of Kona Bay Estates. The simple seaside style will melt all of your cares away as you sip on your Mai Tai in the cool shade of the deep, covered lanai. Experience the feel of...

    Pool
    FREE CANCELLATION

    $525 to $555/night

  13. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    One of West Maui's most exclusive legally permitted rental properties, the Makena Aloha Estate offers exceptional ocean and mountain views, with gated exclusive privacy and seclusion. With 4,400 square feet of interior dwelling space, this...

    Pool Hot Tub

    $1,538 to $3,075/night

  14. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Wonderful ocean views from this spacious penthouse level studio. The owners have completed a beautiful remodel featuring tile floors and a new sofa-sleeper. The full kitchen was recently re-done with new appliances, granite counter tops, new...

    Pool Hot Tub
    FREE CANCELLATION

    $185 to $625/night

  15. CONDOMINIUM
    Kaanapali Shores 819

    Kaanapali Shores 819

    LAHAINA, HI

    This beautiful 1-bedroom, 1-bathroom oceanfront condominium provides everything you need for your vacation in paradise. With spectacular views of the ocean from the 8th floor and a spanning view of the beautiful resort, you can’t beat the view...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $406/night

  16. 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

    $161 to $399/night

  17. APARTMENT
    Kahana Reef 201

    Kahana Reef 201

    Lahaina, HI

    Work hours are Monday-Friday 8am-5pm but heavy/loud work will not begin until after 9 am. Part of the parking lot will be blocked off as well, but that should not pose a parking problem other than you may have to walk farther to the apartment.This...

    Pool
    FREE CANCELLATION

    $173 to $384/night

  18. CONDOMINIUM
    Kihei Akahi C-616

    Kihei Akahi C-616

    Kihei, HI

    Imagine yourself sitting on the lanai with a drink in hand, watching the gorgeous colors of the Hawaiian sunset! This is a perfect budget getaway. Come explore the island! See gorgeous beaches, taste the island cuisine, shop the local businesses and...

    Pool
    FREE CANCELLATION

    $130 to $474/night

  19. CONDOMINIUM
    Island Surf 409

    Island Surf 409

    Kihei, HI

    This adorable new 1bd/1ba condo sits across from Kalama Park in the heart of beautiful Kihei. You'll get to enjoy stunning ocean and mountain views, AC, and all the comforts of home!If you're looking for a place to relax and enjoy Maui, look no...

    Pool
    FREE CANCELLATION

    $150 to $463/night

  20. CONDOMINIUM
    Kaleialoha 205

    Kaleialoha 205

    Lahaina, HI

    A direct Beach/Oceanfront condo with an amazing view. Beach and ocean access for swimming, snorkeling, whale watching and relaxing in the sun.You can't get closer to the ocean than this unless you're on a boat. Watch the whales December through...

    Pool
    FREE CANCELLATION

    $186 to $331/night

  21. HOUSE
    Mahuahua Hale

    Mahuahua Hale

    Kailua Kona, HI

    This 2700+ square ft. house is perfect for entertaining family and friends! With so much space you can accommodate everyone's needs; whether that be barbecuing down by the pool with friends or finding a quiet, private spot to relax with a favorite...

    Pool
    FREE CANCELLATION

    $525 to $642/night

  22. CONDOMINIUM
    Kihei Alii Kai A207

    Kihei Alii Kai A207

    Kihei, HI

    Brand New Renovation! This spacious 1-bedroom, 1 bathroom condo is fully furnished and offers AC, wifi, cable, Dvd player, hairdryer, an in-unit washer and dryer, iron/ironing board, and so much more! You'll also get to enjoy the brand new sofabed...

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $474/night

  23. CONDOMINIUM
    Kaleialoha 210

    Kaleialoha 210

    Lahaina, HI

    Imagine yourself staying at this incredible 1 bedroom Ocean Front Condo!!Views of the gorgeous Pacific Ocean and the neighboring islands from your lanai. Watch sea turtles eat seaweed off of the coral right below the lanai as well as watch whales...

    Pool
    FREE CANCELLATION

    $159 to $584/night

  24. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    'Kona Bubbles' is a absolute spectacular property that Knutson & Associates is extremely proud to be newly representing as of November 2018. A gorgeous home in gated Meilani View Estates with ocean views just above Kailua Kona. Recently finished in...

    Pool
    FREE CANCELLATION

    $1,320 to $1,395/night

  25. 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

    $1,139 to $1,534/night

  26. 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 $773/night

  27. 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

    $129 to $468/night

  28. 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

  29. CONDOMINIUM
    Kamaole Sands 5-313

    Kamaole Sands 5-313

    Kihei, HI

    Ocean and garden views close to the pool. Enjoy beautiful sunsets every evening from your private lanai in this beautifully updated third floor unit! This one bedroom (plus sleeper sofa), two bath, 818 square foot condo is ideal for families or for...

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $463/night

  30. 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

    $134 to $463/night