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
     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Kaunakakai, HI

    You will feel so comfortable and "at home" in the condo that you will be reluctant to leave, but there are other wonderful experiences awaiting you on the grounds of Wavecrest. Wander through the lush tropical grounds, enjoy the fabulous pool right...

    Pool
    FREE CANCELLATION

    $158 to $191/night

  2. HOUSE
    Hale Lokahi

    Hale Lokahi

    Waialua, HI

    Hale Lokahi - House of Peace and Serenity - This home is located in one of the best kept, secret neighborhoods on the north shore. Right on a white sand beach, this family-owned house is perfect for your vacation in paradise.. This 4 bedroom, 2...

    FREE CANCELLATION

    $683 to $992/night

  3. CONDOMINIUM
    Hear the Waves!! Honua Kai- Hokulani 306

    Hear the Waves!! Honua Kai- Hokulani 306

    Kaanapali, HI

    UPGRADED OCEAN/MOUNTAIN VIEW 2 bed/2 bath - GREAT VALUE!*This condo is so close to the beach you can hear the waves crashing!This 1240 Sq ft OCEAN VIEW condo has been upgraded with new DESIGNER FURNISHINGS, SMART TV and TRAVERTINE FLOORING...

    Pool Hot Tub

    $436 to $1,596/night

  4. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Hale Ili Ili is an oceanfront gated four-plex in Kihei Maui Hawaii. The property lends itself to a very private and relaxed atmosphere with breathtaking sunsets, sounds of the ocean and rustling palm trees. Many whales, turtles, dolphins and rays...

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  5. HOUSE
    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    Lahaina, HI

    This premium oceanfront Two Bedroom, Two Bath condo is conveniently located on the ground level. Master Bedroom has a King Bed with a private bathroom. Second Bedroom has a queen bed; and the living room has a queen sofa bed for the extra guests....

    Pool Hot Tub
    FREE CANCELLATION

    $516 to $620/night

  6. CONDOMINIUM
    Kaanapali Shores Studio 642

    Kaanapali Shores Studio 642

    Lahaina, HI

    Relax and enjoy the serenity at Ka'anapali Shores Resort! Our adorable studio suite has been beautifully remodeled to sleep four guests comfortably with a king size bed and a full size sofa pull out for a second bed. The fully appointed kitchen is...

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $359/night

  7. HOUSE
    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Lahaina, HI

    Our Junior Suite on the TENTH Floor is spacious and well-appointed with a King Bed as well as a sofa bed for the occasional guest. You will find seating arrangements for relaxing and dining. There is plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  8. HOUSE
    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Kaanapali, HI

    Our Junior Suite is spacious and well-appointed with a Queen Bed and seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and personal items. The kitchen comes fully equipped with all the modern...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  9. HOUSE
    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Lahaina, HI

    Lovely Oceanfront Junior Suite that features one large room with fully equipped kitchen and bath. Queen-size bed (Sleeps 2). Can accommodate 3 people with added roll-away. Located on the shores of Ka‘anapali Beach in West Maui, Maui Kai is an...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  10. CONDOMINIUM
    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    Kihei, HI

    Ma'alaea Surf, Unit C5, is a conveniently located ground floor unit, just steps away from the small pool. This luxurious unit features a fully furnished kitchen, large living room and a large master suite with a king bed. Enjoy the ocean views and...

    Pool
    FREE CANCELLATION

    $259 to $428/night

  11. CONDOMINIUM
    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit D5 - Newly renovated, and perfectly located, D5 is a ground floor unit, approximately 5 steps from the white sandy beach. This stylish unit features a new kitchen with top grade electrical appliances. Enjoy the large master suite...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  12. CONDOMINIUM
    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Ma'alaea Surf, Unit F5 is a townhouse unit situated on the second floor offering guest total privacy. With the latest in contemporary upgrades, this gorgeous unit features a fully furnished modern kitchen and the convenience of a second bedroom and...

    Pool
    FREE CANCELLATION

    $343 to $540/night

  13. CONDOMINIUM
    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    Kihei, HI

    Ma'alaea Surf, Unit G4 is a conveniently located ground floor unit, just steps away from the large pool. This warm luxurious unit features a recently upgraded fully furnished kitchen, large master suite with King size bed and a queen size sofa bed...

    Pool
    FREE CANCELLATION

    $259 to $428/night

  14. CONDOMINIUM
    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit A2 is a conveniently located ground floor condo, just steps from the beach. This luxurious unit features a full kitchen and dining table. The master bedroom has a king sized bed. The large living room has expansive views and a...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  15. CONDOMINIUM
    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit H4 is deluxe in every sense. H4 is an ideally located ground floor unit, approximately 5 steps from the white sandy beach. This exceptional unit features a full kitchen, second bedroom and bath.Enjoy the ocean views and Maui's...

    Pool
    FREE CANCELLATION

    $416 to $664/night

  16. CONDOMINIUM
    Lahaina Roads 309

    Lahaina Roads 309

    Lahaina, HI

    This unit was just remodeled. Everything is fresh and new, with many details provided for your comfort. Lahaina Roads is located 50 feet from the ocean on Front Street in the historical town of Lahaina. The condominium overlooks a beautiful pool...

    Pool
    FREE CANCELLATION

    $213 to $438/night

  17. 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

  18. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-202

    Keauhou Kona Surf & Racquet Club #5-202

    Kailua Kona, HI

    BRAND NEW VACATION RENTAL WITH BRAND NEW OWNERSHIP!Welcome to #5-202 at the Keauhou Kona Surf & Racquet Club! The new owners are excited to have their new property that's never been rented before be placed as a new Vacation Rental!DIRECT OCEANFRONT...

    Pool
    FREE CANCELLATION

    $302 to $326/night

  19. 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

  20. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Ma'alaea Surf, Unit G10 is a two story townhouse unit with vaulted ceilings. Situated on the second floor this unit has a very open feel and offers our guest total privacy. This unit has a large lanai, stunning ocean views and overlooks the large...

    Pool
    FREE CANCELLATION

    $343 to $540/night

  21. CONDOMINIUM
    Honua Kai- Konea 924- One Bedroom Ocean View! Renovated!

    Honua Kai- Konea 924- One Bedroom Ocean View! Renovated!...

    Kaanapali, HI

    NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the Konea building at Honua Kai. This condo overlooks the construction site. There may be noise and dust on work days during construction hours from 8am to 5pm.NOW FEATURING...

    Pool Hot Tub

    $305 to $1,003/night

  22. CONDOMINIUM
    Maui Kai 601

    Maui Kai 601

    Lahaina, HI

    Beautiful remodel just completed May 2019!Enjoy the brand new lanai, with incredible views to enjoy from the comfort of chaise chairs or the dining set. Luxurious tile throughout the condo, gorgeous granite counters and all new appliances in the...

    Pool
    FREE CANCELLATION

    $249 to $624/night

  23. 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

  24. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Spend your dream vacation on Maui at the Whaler on beautiful Kaanapali beach! Enjoy stunning West Maui sunsets and gorgeously landscaped grounds!Relax on the lanai with a cup of coffee or a cocktail where you can see from Mauka to Makai (from...

    Pool
    FREE CANCELLATION

    $411 to $1,160/night

  25. 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
    FREE CANCELLATION

    $124 to $311/night

  26. CONDOMINIUM
    Kaanapali Shores 403

    Kaanapali Shores 403

    Lahaina, HI

    Relax on our 4th 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 403 lanai has views of the ocean,spectacular sunsets, and whales in...

    Pool Hot Tub
    FREE CANCELLATION

    $374 to $1,195/night

  27. 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

  28. CONDOMINIUM
    Hale Kai 2 Ko Olina Beach Villa (B906)

    Hale Kai 2 Ko Olina Beach Villa (B906)

    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

    $408 to $1,500/night

  29. CONDOMINIUM
    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    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.L I V E C A L E N D A RIf the calendar shows as available, the Villa is not reserved and...

    Pool Hot Tub

    $745 to $1,668/night

  30. CONDOMINIUM
    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    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 $1,668/night