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
    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

  2. 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

  3. 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

    $163 to $373/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

    $193 to $630/night

  5. 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

    $188 to $636/night

  6. 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 $426/night

  7. CONDOMINIUM
    Pohailani #223

    Pohailani #223

    Lahaina, HI

    Guests are sure to enjoy a memorable family vacation in this fully furnished, 2 bedroom/1 bath condo. The main bedroom has a queen sized bed, while the other bedroom is furnished with 2 Twins. It is perfect for a family as it can sleep 4 people....

    Pool
    FREE CANCELLATION

    $183 to $353/night

  8. 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

  9. 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 CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $687 to $1,668/night

  10. 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

  11. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Hale Pua (“House of Flowers”) is one of the few 5 bedroom/6 full bath oceanfront vacation rental homes with its own private pool & spa in the Kailua-Kona area. For recent candid photos and input from guests, please visit our FB page,...

    Pool Hot Tub

    $1,938 to $2,627/night

  12. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Get ready for the trip of a lifetime! Royal Kahana 106 is a fantastic unit with tons of space and amazing ocean views! Equipped with cable, wifi, washer/dryer and more. You'll have all the comforts of home! Be sure to take full advantage of the...

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $498/night

  13. CONDOMINIUM
    Paki Maui 424

    Paki Maui 424

    Lahaina, HI

    Waterfront condo at an oceanfront resort on the Kaanapali Coast. Welcome to the island of Maui! Spend your days outside in the tropical sunshine, take advantage of the beach access from your resort and return home to the shared pool and a hot tub....

    Pool Hot Tub
    FREE CANCELLATION

    $284 to $608/night

  14. 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

  15. 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

  16. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Nohonani 405 is a beautiful two bedroom one and a half bath unit on the fourth floor, with vaulted ceilings and a breathtaking ocean view. Ocean views can be seen from the kitchen, dining areas, living room and master bedroom. As with all the...

    Pool
    FREE CANCELLATION

    $274 to $403/night

  17. 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

  18. 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...

    Pool
    FREE CANCELLATION

    $173 to $611/night

  19. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Experience a vacation of a lifetime in this massive oceanfront custom home tucked away in an exclusive and quiet gated community along the Kona coast. A pond with a waterfall, filled with flowers welcomes you upon entering this beautiful custom...

    Pool Hot Tub

    $1,150 to $1,605/night

  20. HOUSE
    Kona Bay Bliss

    Kona Bay Bliss

    Kailua Kona, HI

    This incredible home is secluded in a 24 hour guard gated oceanfront community, yet is close to all that Kona has to offer. It is located just a short walk from the classic old Hawaiian town of Kailua and the start/finish of the Ironman. In all of...

    Pool Hot Tub

    $1,343 to $2,014/night

  21. 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

  22. 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

    $161 to $366/night

  23. 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

  24. 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

    $153 to $543/night