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
    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

  2. CONDOMINIUM
    Hale Ono Loa 106

    Hale Ono Loa 106

    Lahaina, HI

    Enjoy this West Maui Ocean Front Resort with lush grounds which includes a pool, lounge area, shuffleboard, picnic area, BBQ’s. Relax on a Lanai and enjoying sunset dinners and beautiful views of Lanai and Molokai in the distance. Maui is known...

    Pool
    FREE CANCELLATION

    $199 to $200/night

  3. CONDOMINIUM
    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    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 can be booked instantly...

    Pool Hot Tub

    $455 to $1,204/night

  4. CONDOMINIUM
    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    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

    $582 to $1,668/night

  5. CONDOMINIUM
    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    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

    $617 to $1,784/night

  6. CONDOMINIUM
    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    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

    $594 to $1,784/night

  7. CONDOMINIUM
    Hale Kahakai Ko Olina Beach Villa (O212)

    Hale Kahakai Ko Olina Beach Villa (O212)

    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 Villa is not reserved and can be...

    Pool Hot Tub

    $501 to $1,500/night

  8. 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

  9. 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

  10. CONDOMINIUM
    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    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

    $508 to $1,384/night

  11. CONDOMINIUM
    Hoyochi Nikko #109

    Hoyochi Nikko #109

    Lahaina, HI

    One bedroom condo located in beautiful west Maui. For those wishing additional solitude, this is an end unit with a new queen bed and bedroom air conditioning. All units are fully equipped with Cable TV, DVD, CD player, washer/dryer, and...

    Pool
    FREE CANCELLATION

    $201 to $296/night

  12. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    An incredibly comfortable unit! This renovated one bedroom unit fronts directly on a beautiful white sand beach. You'll have just enough lawn area to stretch out and shake the sand off before stepping directly into your beautiful ocean side living...

    FREE CANCELLATION

    $161 to $308/night

  13. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    The Kahana Sunset Welcomes you with This unique condo is a beachfront property on the world famous West Coast of Maui between Kaanapali and Kapalua. Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) •...

    Pool
    FREE CANCELLATION

    $251 to $389/night

  14. 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

  15. CONDOMINIUM
    Hale Pineapple

    Hale Pineapple

    Lahaina, HI

    Welcome to Hau'oli Hala Kahiki, a hidden gem in Honokowai on Maui's beautiful west shore. Located in the quiet, low-density Kaleialoha building, this sweet 1 bedroom/1 bath condo sits on the ground floor, so no stairs to climb or having to wait for...

    FREE CANCELLATION

    $180 to $239/night

  16. HOUSE
    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    Kaanapali, HI

    Our One Bedroom Corner unit is spacious and well-appointed with a King Bed in the bedroom and a Queen sofa bed in the living room. There is seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  17. HOUSE
    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Lahaina, HI

    This beautiful sixth floor oceanfront condo has a perfect view of Molokai. The tropical décor and king murphy bed help make your stay comfortable and relaxing. The fully equipped kitchen is great for a quick bite or a full meal. You will find...

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $341/night

  18. HOUSE
    Best Rate- 1 Bedroom Corner Oceanfront 12

    Best Rate- 1 Bedroom Corner Oceanfront 12

    Kaanapali, HI

    One Bedroom Corner - King Bed, NO sofa bed, enclosed lanai which makes the unit , Flat screen TV - hardwood floors; Livingroom is tiled in white. This condo will accommodate a maximum of two people, four with queen areo bed as extra bedding. The...

    Pool Hot Tub
    FREE CANCELLATION

    $351 to $423/night

  19. HOUSE
    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    Kaanapali, HI

    This beautiful One Bedroom Corner unit was recently renovated and has a breathtaking view! Featuring a King Bed, Queen Sofa Sleeper, full kitchen, all done in the warm island style. Wake up and have breakfast on your spacious open lanai while you...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  20. HOUSE
    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Lahaina, HI

    {Jr. Suite (Studio) - King bed; Flat screen TV; extended lanai} MAUI KAI 1006 This oceanfront junior suite is a bright, airy unit decorated in light tones, pale off-white tile in the kitchen and bath, with carpet in the center living area of the...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  21. HOUSE
    Junior Suite Oceanfront #302

    Junior Suite Oceanfront #302

    Lahaina, HI

    This is a lovely Studio featuring a Queen sized Murphy Bed. The bed is easily placed into the wall to expand your living space if you so desire. One of Maui Kai’s little gems is unit 302. In colorful, floral designs, this room presents itself as a...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  22. HOUSE
    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    Kaanapali, HI

    One Bedroom - Flat screen TV ; King bed, 2 Twins on lanai. (NO SOFA BED) This unit is part of the Maui Kai Condos a Lahaina hotel located on the Kaanapali Beach less than one mile from the Kapalua West Maui Airport. This unit features an heated...

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  23. CONDOMINIUM
    Valley Isle #1106

    Valley Isle #1106

    Lahaina, HI

    From the time you open your front door a magnet pulls you across the room directly to the balcony. It takes a few swallows to get that lump cleared from your throat. This is the view you see on the travel channel, travel books, magazines, and post...

    Pool
    FREE CANCELLATION

    $156 to $251/night

  24. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 215 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

    $275 to $413/night

  25. CONDOMINIUM
    Honua Kai- Konea 314- One bedroom with Rainbow Views! 1b/1b

    Honua Kai- Konea 314- One bedroom with Rainbow Views! 1b...

    Kaanapali, HI

    HAPPY HOUR ON US! FREE $25 Dukes gift card for stays between 7/11/19-12/19/19. 5-night minimum, for bookings made after 7/9/19, may not be combined with any promo pricing. WOW! Just Updated! Beautiful new light & bright PORCELAIN TILE FLOORS...

    Pool Hot Tub

    $316 to $1,003/night

  26. CONDOMINIUM
    Honua Kai- Konea 1024- One Bedroom Penthouse Ocean View! 1b/1b

    Honua Kai- Konea 1024- One Bedroom Penthouse Ocean View!...

    Kaanapali, HI

    HAPPY HOUR ON US! FREE $25 Dukes gift card for stays between 7/11/19-12/19/19. 5-night minimum, for bookings made after 7/9/19, may not be combined with any promo pricing. GREAT DEAL! TOP FLOOR - OCEAN VIEW! OCEAN VIEWS FROM ONE BEDROOM PENTHOUSE...

    Pool Hot Tub

    $316 to $1,003/night

  27. CONDOMINIUM
    Kahana Villa F-410

    Kahana Villa F-410

    Lahaina, HI

    F-410 is the newest, most beautifully upgraded unit around - and the prices are FANTASTIC! There is literally nothing more you could ask for in a vacation rental condo. Everything is available to you. Upgraded kitchen, granite counter tops,...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $263/night

  28. CONDOMINIUM
    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zone District and is not affected by the passage of Bill 89. L I V E C A L E N D A R If the calendar shows as available, the property can be booked...

    Pool Hot Tub

    $455 to $1,204/night

  29. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #6-104

    Keauhou Kona Surf & Racquet Club #6-104

    Kailua Kona, HI

    **BRAND NEW PROPERTY IN OUR INVENTORY! AIR CONDITIONING INSTALLED AS OF SEPTEMBER 2018!** Unit#6-104 is a well-maintained 2BR/2BA ground floor unit in a 15-acre, gated oceanfront complex at the Keauhou Kona Surf & Racquet Club. It's also an end...

    Pool
    FREE CANCELLATION

    $256 to $292/night

  30. 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