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. 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

  3. 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 $319/night

  4. CONDOMINIUM
    Waiohuli Beach Hale #D-127

    Waiohuli Beach Hale #D-127

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $223 to $465/night

  5. CONDOMINIUM
    Hale Lokahi KoOlina Beach Villa (O701)

    Hale Lokahi KoOlina Beach Villa (O701)

    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

    $397 to $1,204/night

  6. 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 CALENDARIf the calendar shows as available, the property is not reserved and can be...

    Pool Hot Tub

    $397 to $1,204/night

  7. 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 $614/night

  8. 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

  9. CONDOMINIUM
    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Waipuilani Park 2BR w/ Pool- Walk to Beach, Shops

    Kihei, HI

    Overlooking tranquil Waipuilani Park, this oceanfront 2BR condo boasts beautiful unobstructed views from the private lanai. As part of the quiet complex at Leinaala, you’ll enjoy access to a grill area and a sparkling pool (steps from your...

    Pool
    FREE CANCELLATION

    $142 to $504/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. CONDOMINIUM
    Oceanfront Nohonani- Unforgettable Views

    Oceanfront Nohonani- Unforgettable Views

    Lahaina, HI

    This recently updated 2BR/2BA oceanfront condo at Nohonani offers incredible views of both Lanai and Molokai from its fourth-floor perch. Sip drinks on the private lanai while taking in the sunset over the Pacific.Enjoy resort-style amenities,...

    Pool
    FREE CANCELLATION

    $133 to $619/night

  12. CONDOMINIUM
    Hale Welo Ko Olina Beach Villa (B806)

    Hale Welo Ko Olina Beach Villa (B806)

    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

    $432 to $1,500/night

  13. 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

  14. CONDOMINIUM
    New! Updated! Modern, Maui Beachfront with Central A/C

    New! Updated! Modern, Maui Beachfront with Central A/C

    Lahaina, HI

    Most frequently asked questions re: payments, cancellations, our home, and the area, can be answered in the property info, guest reviews, and pictures, below. We kindly ask that you read all of these details, as we offer a lot of amenities that...

    Pool Hot Tub
    FREE CANCELLATION

    $561 to $731/night

  15. 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 $437/night

  16. CONDOMINIUM
    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    Kailua Kona, HI

    PROPERTY OVERVIEWPrime surfing and snorkeling are within steps of this 2BR/2BA condo, situated right across the street from Kahalu’u Beach. The ultra-convenient location is also close to Kona Town and Keauhou.Boasting beautiful ocean views from...

    Pool Hot Tub
    FREE CANCELLATION

    $148 to $460/night

  17. CONDOMINIUM
    Kaanapali Shores 538

    Kaanapali Shores 538

    Lahaina, HI

    Experience the essence of Hawaii at the Kaanapali Shores Beachfront Resort located on legendary Kaanapali Beach. Kaanapali Beach has been named the “Best Beach in the World” by Conde Nast Magazine year after year. The breathtaking oceanfront...

    Pool
    FREE CANCELLATION

    $206 to $423/night

  18. 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

    $125 to $311/night

  19. 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 muchIncluded in our fabulous price...

    FREE CANCELLATION

    $180 to $239/night

  20. 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

  21. 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

  22. CONDOMINIUM
    Leinaala Oceanfront #104

    Leinaala Oceanfront #104

    Kihei, HI

    Leinaala Condo - 1BR with the Ocean in Your BackyardSalty breezes and gentle waves remind you that the ocean is right in your backyard at our one-bed, one-bath condo at Leinaala. Our ground-floor lanai lets guests walk directly onto the beach, or...

    Pool
    FREE CANCELLATION

    $232 to $465/night

  23. CONDOMINIUM
    Sealodge G8

    Sealodge G8

    Princeville, HI

    Sealodge G8: This top floor 2br/2ba condo offers incredible oceanfront views from every the EXTRA window added in the living room to provide even more ocean views! From your private lanai, you look all the way down the Anini reef to the light...

    Pool
    FREE CANCELLATION

    $238 to $275/night

  24. 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 $1,568/night

  25. CONDOMINIUM
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Special discount for open August dates! Sealodge J2: Enjoy the best view at Sealodge from this very private end unit! Amazing oceanfront views, ground floor convenience, and privacy - it's the perfect honeymoon hideaway. You'll find a comfortably...

    Pool
    FREE CANCELLATION

    $214 to $257/night

  26. CONDOMINIUM
    Kauhale Makai #330

    Kauhale Makai #330

    Kihei, HI

    Hawaiian for "Village By The Sea," the Kauhale Makai complex is an oceanfront property located in Kihei. This is one of a few buildings in the area with central air conditioning - not window units. This condo stays as cool as you like it. Kihei is...

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $266/night

  27. 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

    $458 to $1,160/night

  28. 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

  29. 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

  30. CONDOMINIUM
    Nohonani #202

    Nohonani #202

    Lahaina, HI

    Unit 202 is a beautiful two bedroom 2 bath unit on the 2nd floor with breathtaking ocean views from the kitchen, dining areas, living room and master bedroom. As with all the Nohonani units, the master bedroom is ocean side and has a sliding door...

    Pool
    FREE CANCELLATION

    $274 to $403/night