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. TOWNHOUSE
    Ko Olina Kai Condo (1085E)

    Ko Olina Kai Condo (1085E)

    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

    $218/night

  2. 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

  3. CONDOMINIUM
    Paki Maui 415

    Paki Maui 415

    Lahaina, HI

    Come enjoy the Paki Maui Oceanfront Resort! This 1 bedroom, 1 bath, lush garden view condo is the perfect place for couples, small families and adventurers looking to experience and explore the island for all the wondrous places and memories it...

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $174/night

  4. 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

  5. CONDOMINIUM
    Hale Ono Loa 402

    Hale Ono Loa 402

    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

    $219 to $225/night

  6. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Ko Olina Kai is a peaceful gated community that offers all the tranquil privacy you could desire! The interior is spacious and homey with 2 bedrooms, 2 baths, a living room with an adjacent dining space, and a kitchen. This outstanding villa offers...

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $158/night

  7. CONDOMINIUM
    Waikiki Grand Condominium 922 *Legal Vacation Rental

    Waikiki Grand Condominium 922 *Legal Vacation Rental

    Honolulu, HI

    Our LEGALLY ZONED vacation rental at the Waikiki Grand, 134 Kapahulu Avenue.    Absolutely awesome unit located just a block from the beach. In fact, you can see the ocean and the beach from the front door! Large unit with kitchen and path...All...

    Pool
    FREE CANCELLATION

    $107 to $596/night

  8. APARTMENT
    Condo with Ocean View! Right on a Golf Course & Minutes from the Beach!

    Condo with Ocean View! Right on a Golf Course & Minu...

    Waikoloa, HI

     This is a wonderfully, updated condo in Waikoloa Village with sweeping ocean views!  Don't miss out on staying here and enjoying quiet sunsets on the lanai overlooking the Trent Jones golf course with 180 views of the coastline.  This complex...

    Pool
    FREE CANCELLATION

    $152 to $183/night

  9. VILLA
    Kapalua Golf Villa 25T4 Gold Ocean View

    Kapalua Golf Villa 25T4 Gold Ocean View

    Kapalua, HI

    This lovely Villa has the feeling of casual island elegance with it's open style kitchen and living-dining area. Featuring a luxury gourmet kitchen with quality stainless steel appliances, surrounded by natural stone and warm exotic woods. It...

    Pool

    $294 to $563/night

  10. VILLA
    Kapalua Bay Villa 12B2 Gold Ocean View

    Kapalua Bay Villa 12B2 Gold Ocean View

    Lahaina, HI

    Wake up every morning to ocean breezes and spectacular 180° panoramic views of the Pacific Ocean, neighboring islands, and Maui’s north shore coast line. Within easy walking distance to beaches and coastal walking trails. Newly remodeled by an...

    Pool

    $594 to $1,063/night

  11. VILLA
    Kapalua Golf Villa 25V2 Gold Ocean View

    Kapalua Golf Villa 25V2 Gold Ocean View

    Kapalua, HI

    If you enjoy the serene and tranquil feel of the Golf Villas but want a nice ocean view, you will be delighted with this little gem. It is the best of both worlds. Just steps from the pool and green or a short walk to the beach. This lovely villa...

    Pool

    $281 to $494/night

  12. VILLA
    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Lahaina, HI

    E Komo Mai 'Welcome' to Aloha Vacation Villa’s newest WATERFRONT vacation property! Nestled in the luxurious Kapalua area in north Maui, the spacious interior of this 2 bed 3 bath tranquil retreat is the perfect blend of premium comfort and...

    Pool

    $594 to $1,063/night

  13. VILLA
    Kapalua Ridge Villa 1214 Gold Ocean View

    Kapalua Ridge Villa 1214 Gold Ocean View

    Kapalua, HI

    Contact Manager about last minute Christmas Special for 2018! This luxurious retreat will spoil you forever. You’ll feel like you’re on top of the world as you take in spectacular views of the Pacific Ocean and the lush green landscape that...

    Pool

    $494 to $856/night

  14. CONDOMINIUM
    Kamaole Sands #7-304

    Kamaole Sands #7-304

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Located across the street from Kamaole Beach III. Whale watch, swim, snorkel, walk miles on the beach and watch the most amazing sunsets imaginable. There are 15 acres of lush tropical...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $365/night

  15. CONDOMINIUM
    Kona Pacific B511

    Kona Pacific B511

    Kailua Kona, HI

    Kona Pacific B-511 is a brand new Vacation Rental that Knutson & Associates Property Management is proud to represent as a new addition in August 2017! There are magnificent ocean views from the Main Lanai & Bedroom Lanai for your viewing pleasure....

    Pool
    FREE CANCELLATION

    $158 to $197/night

  16. CONDOMINIUM
    HOL 119

    HOL 119

    Lahaina, HI

    Beautifully updated ground floor unit. Private and unique! Enter through your own private entrance and enjoy the distinctive qualities of this exceptional condo! Large lanai with direct ocean views! A/C in both bedrooms. All stainless steel...

    Pool
    FREE CANCELLATION

    $277 to $502/night

  17. CONDOMINIUM
    Kaleialoha 112

    Kaleialoha 112

    Lahaina, HI

    Enjoy the white sand beach and beautiful tiled pool while you step out of your large ground floor lanai to a gorgeous lawn and lounge area right on the ocean. Five steps to SWIMMING, SNORKELING, SURFING on the PRIVATE white sand beach! See whales...

    Pool
    FREE CANCELLATION

    $167 to $285/night

  18. CONDOMINIUM
    Aina Nalu B204

    Aina Nalu B204

    Lahaina, HI

    Relax and unwind at our beautiful 2 bedroom, 2 bathroom condo at Aina-Nalu. This tasteful unit features high vaulted ceilings and sky lights to create a bright, beautiful, open environment. There is an ultra comfortable King bed in the master...

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $410/night

  19. CONDOMINIUM
    Pohailani Maui 115

    Pohailani Maui 115

    Lahaina, HI

    Our remodeled villa has all of the modern amenities of home! It is situated half way between Kaanapali and Kapalua Bay with plenty of shopping and restaurants near by. This beautifully furnished 2 bedroom 1 bath condo sleeps up to 6 people and has a...

    Pool
    FREE CANCELLATION

    $199 to $281/night

  20. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    Lahaina, HI

    This rarely-available top-floor penthouse condominium is the ultimate in luxury living. Konea 743 boasts amazing ocean views of Maui and the surrounding islands. This spacious suite includes two bedroom, two full baths and a sofa-bed to accommodate...

    Pool Hot Tub
    FREE CANCELLATION

    $513 to $988/night

  21. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kailua Kona, HI

    What is better than a Hawaiian sunset over the ocean? A sunset over the ocean that you can take in from the privacy of your tropical home-away-from-home! With nearly 5,000 square feet of indoor/outdoor living space, including a lanai with a pool...

    Pool

    $689 to $1,678/night

  22. CONDOMINIUM
    Hale Koa Ko Olina Beach Villa (O222)

    Hale Koa Ko Olina Beach Villa (O222)

    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...

    $501 to $1,500/night

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

    Pool Hot Tub

    $455 to $1,204/night

  24. 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

  25. CONDOMINIUM
    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    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

  26. 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

  27. CONDOMINIUM
    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    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

    $571 to $1,668/night

  28. 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

  29. 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

  30. 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