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
    Paniolo Hale R2

    Paniolo Hale R2

    Maunaloa, HI

    This is a lovely one bedroom, 2 bath condo with open beam ceilings and hardwood floors. Ground floor level has a treetop view living area with a large screened lanai, kitchen,full bath, and dining/living room with flat screen TV/VCR, high speed...

    Pool
    FREE CANCELLATION

    $141 to $169/night

  2. CONDOMINIUM
    Waikiki Dream Vacation

    Waikiki Dream Vacation

    Honolulu, HI

    Beautifully remodeled 2 bedroom 2 bath with large lanai facing Diamond Head with Ocean and Mountain Views. free assigned, covered and secure parking. One queen bed in master bedroom. 2 twins in the view suite can be put together. Located centrally...

    Pool Hot Tub

    $292 to $352/night

  3. HOTEL ROOM
    Hotel Molokai Hotel Room 201

    Hotel Molokai Hotel Room 201

    Kaunakakai, HI

    Cute little one room studio with King bed and two twins.  Unit is located upstiars and has a small kitchen with  4 burner stove top, microwave, low fat fryerr, coffee maker, toaster and other small applicance to be able to cook some.  Hotel...

    Pool
    FREE CANCELLATION

    $141 to $169/night

  4. 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

  5. CONDOMINIUM
    Eldorado J111

    Eldorado J111

    Lahaina, HI

    The weather is ideal in Maui year round. MAUI ELDORADO HAS THE ONLY PRIVATE BEACH CABANA ON KAANAPALI BEACH FOR MAUI ELDORADO GUESTS ONLY. Experience Maui Eldorado in the Heart of Kaanapali - an affordable vacation in paradise. Maui Eldorado is...

    Pool
    FREE CANCELLATION

    $174 to $299/night

  6. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    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

    $833 to $2,016/night

  7. CONDOMINIUM
    Hoyochi Nikko #201

    Hoyochi Nikko #201

    Lahaina, HI

    One bedroom with high vaulted ceilings (additional sleeping capacity on sofa bed in living room). Brand new memory foam mattress. This unit has air conditioning in the bedroom along with a comfortable queen size bed. This condo is fully equipped...

    Pool
    FREE CANCELLATION

    $218 to $369/night

  8. CONDOMINIUM
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Book today and Fall in LOVE with "HiiLani" (In the arms of Heaven)... You will feel like you have gone back in time to the true Hawaiian experience in this condo just 15 FT from the water's edge! 204 Pohailani Welcomes you with so much ALOHA.....

    Pool
    FREE CANCELLATION

    $199 to $264/night

  9. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    Book today and Fall in LOVE with "THE LIL GRASS SHACK" You will feel like you have gone back in time to the true Hawaiian experience in this condo, just 10 FT from the water's edge! 103 Pohailani Welcomes you with so much Included in our...

    FREE CANCELLATION

    $187 to $239/night

  10. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    AINA NALU K-205 Welcomes you with Aloha... This unique condo, in the heart of Old Lahaina Town, is a perfect vacation spot! K-205 was remodeled with the touch of ALOHA in 2017. Included in our fabulous price are many owner-supplied extras such...

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $239/night

  11. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Nohonani 300 has recently completed a brand new renovation. Improvements include new carpeting and beautiful furnishings. This is an end unit on the third floor giving added privacy and a spectacular crows nest view of the outer islands and golden...

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $403/night

  12. CONDOMINIUM
    Nohonani #105

    Nohonani #105

    Lahaina, HI

    Unit #105 is a two bedroom, two bath unit just steps away from the beach. The master bedroom has a king-size bed; and twin beds in the guest bedroom. Free parking and WiFi are provided as well. If you have ever dreamt of lying in bed and going to...

    Pool
    FREE CANCELLATION

    $274 to $403/night

  13. 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 R If the calendar shows as available, the Villa is not reserved...

    Pool Hot Tub

    $740 to $1,668/night

  14. 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

  15. 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

  16. 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

  17. 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

  18. 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

  19. CONDOMINIUM
    Hale Ono Loa #316

    Hale Ono Loa #316

    Lahaina, HI

    Enjoy our tropical paradise – Feel tension melt away when take your first look from our unit and see an unobstructed, breath-taking views of Lana'i, Molokai'i and the vast expanse of ocean. It is magnificent at all times of day. Relax to the...

    Pool
    FREE CANCELLATION

    $178 to $263/night

  20. CONDOMINIUM
    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    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

    $485 to $1,204/night

  21. CONDOMINIUM
    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    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

  22. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    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

    $717 to $1,784/night

  23. 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

    $508 to $1,500/night

  24. CONDOMINIUM
    Cliffs 7303

    Cliffs 7303

    Princeville, HI

    This spacious, comfortable, Princeville condo is an excellent value. At Cliffs 7303, enjoy two lanais, one off the living area with a great ocean view, and one off the master bedroom, with views of the mountains and their waterfalls. This updated...

    Pool Hot Tub
    FREE CANCELLATION

    $214 to $238/night

  25. 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

  26. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    A beautifully updated kitchen allows for cooking family meals in, saving money for activities and adventures. In addition to the flat screen TV and dvd player in the living room, there is also a TV in the bedroom.. Bring your electronic equipment...

    Pool Hot Tub
    FREE CANCELLATION

    $208 to $700/night

  27. CONDOMINIUM
    Wailea Ekolu 1606

    Wailea Ekolu 1606

    Kihei, HI

    Located in beautiful Wailea, this 2bd 2ba condo is on the top floor and boasts high ceilings and a gorgeous ocean view. Visting with a larger group? We have another unit in the same building! Make sure to ask us availability for booking 1604 and...

    Pool
    FREE CANCELLATION

    $299 to $874/night

  28. 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

    $166 to $373/night

  29. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Hale Kamaole is the perfect getaway location for couples or small families! Situated in South Kihei near shopping restaurants, and beautiful beaches, you'll have plenty of options to fully experience Maui. This is a spacious 1 bedroom/ 1 bathroom...

    Pool
    FREE CANCELLATION

    $160 to $544/night

  30. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    The condo is totally renovated and updated. From your private lanai you have a lovely area to sit and dine or just relax with nothing but the crystal blue ocean and the famous Maui sunsets in front, FRONT SEAT WHALE WATCHING from the lanai. Tile...

    Pool Hot Tub
    FREE CANCELLATION

    $253 to $844/night