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. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Hale Pua (“House of Flowers”) is one of the few 5 bedroom/6 full bath oceanfront vacation rental homes with its own private pool & spa in the Kailua-Kona area. For recent candid photos and input from guests, please visit our FB page,...

    Pool Hot Tub

    $1,938 to $2,627/night

  2. 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

  3. 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

  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. 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

  9. 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

  10. 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

  11. CONDOMINIUM
    Turtle Bay The Darrolee**TA-151924326401

    Turtle Bay The Darrolee**TA-151924326401

    Kahuku, HI

    Second story condo. Newly remodeled kitchen cabinets, ceramic tile on main level. Window a/c in bedroom. NO INTERNET OR WIFI Welcome to Kuilima Estates, the condo property located on the grounds of world-renowned Turtle Bay. The condos are...

    Pool
    FREE CANCELLATION

    $202 to $241/night

  12. CONDOMINIUM
    Turtle Bay Bird of Paradise**TA-086947840001

    Turtle Bay Bird of Paradise**TA-086947840001

    Kahuku, HI

    Light, airy, remodeled end unit. Screened lanai on first fairway, close to club house and restaurant. Flat screen TV with VCR/DVD/CD/tape. Jacuzzi tub. Air conditioned bedrooms. WIFI Welcome to Kuilima Estates, the condo property located on the...

    Pool
    FREE CANCELLATION

    $266 to $283/night

  13. CONDOMINIUM
    Turtle Bay Paniolo**TA-202779033601

    Turtle Bay Paniolo**TA-202779033601

    Kahuku, HI

    Upgraded condo. WIFI. Blue Ray player with Netflix access. DVR. Blu Ray player with Netflix access Welcome to Kuilima Estates, the condo property located on the grounds of world-renowned Turtle Bay. The condos are surrounded by two beautifully...

    Pool
    FREE CANCELLATION

    $241 to $254/night

  14. CONDOMINIUM
    Turtle Bay Alea**90-TVU-0263

    Turtle Bay Alea**90-TVU-0263

    Kahuku, HI

    Welcome to Kuilima Estates, the condo property located on the grounds of world-renowned Turtle Bay. The condos are surrounded by two beautifully manicured golf courses, and are the only condos on the North Shore. This is a great place to relax,...

    Pool
    FREE CANCELLATION

    $266 to $283/night

  15. CONDOMINIUM
    Turtle Bay Haupia**TA-136982118401

    Turtle Bay Haupia**TA-136982118401

    Kahuku, HI

    Cool condo that sleeps 8. One of the few units with brand new split AC in living /dining/kitchen areas and loft sleeping area. Plus, window AC units in all bedrooms will keep you cool and comfortable when it's hot outside. Nice new full size sofa...

    Pool
    FREE CANCELLATION

    $277 to $306/night

  16. CONDOMINIUM
    Turtle Bay 19th Hole*TA-017785446401

    Turtle Bay 19th Hole*TA-017785446401

    Kahuku, HI

    Comfy ground floor end unit. A/C in the bedroom. Screened-in lanai with table and chairs. TV has VCR. WiFi Welcome to Kuilima Estates, the condo property located on the grounds of world-renowned Turtle Bay. The condos are surrounded by two...

    Pool
    FREE CANCELLATION

    $139 to $161/night

  17. CONDOMINIUM
    Turtle Bay On The Green**TA-124574924801

    Turtle Bay On The Green**TA-124574924801

    Kahuku, HI

    Air conditioning in the living room. Screened-in lanai with table and 4 chairs. TV in living room with VCR. WIFI. Welcome to Kuilima Estates, the condo property located on the grounds of world-renowned Turtle Bay. The condos are surrounded by two...

    Pool
    FREE CANCELLATION

    $191 to $225/night

  18. CONDOMINIUM
    Ma'alaea Surf Unit #C-8

    Ma'alaea Surf Unit #C-8

    Kihei, HI

    Maalaea Surf Resort is an exceptional beachfront property located in North Kihei offering spectacular ocean views. This property consists of eight two story buildings spread out over five acres of immaculate tropical landscaping. It lies on the...

    Pool

    $268 to $526/night

  19. HOUSE
    Ho'o Maluhia

    Ho'o Maluhia

    Kailua Kona, HI

    This beautiful home features luxury and artistic touches to add a splash of sophistication to your vacation. The beautiful layout, wood floors and cool tiles fill the house. The master bedroom is located on the upper level. This room includes a...

    Pool

    $444 to $730/night

  20. CONDOMINIUM
    Maui Kamaole #M-105

    Maui Kamaole #M-105

    Kihei, HI

    Kamaole Beach #3 is just across from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property and tennis courts...

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $339/night

  21. CONDOMINIUM
    Maui Kamaole #J-103

    Maui Kamaole #J-103

    Kihei, HI

    Kamaole Beach #3 is just across from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property and tennis courts...

    Pool Hot Tub
    FREE CANCELLATION

    $196 to $342/night

  22. CONDOMINIUM
    Luana Kai #A-205

    Luana Kai #A-205

    Kihei, HI

    Luana Kai is a large oceanfront complex in Kihei. It is centrally located to shops, activities, and restaurants. It features a large oceanfront pool, hot tub, shuffleboard, and gas grills for your use. There is an expansive lawn between the...

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $342/night

  23. CONDOMINIUM
    Wailea Ekolu #310

    Wailea Ekolu #310

    Wailea, HI

    Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There are also additional barbecue and picnic areas on the grounds with panoramic views of the ocean and the sunsets. The beautiful Mokapu and Ulua...

    Pool
    FREE CANCELLATION

    $302 to $534/night

  24. CONDOMINIUM
    Kamaole Sands #7-403

    Kamaole Sands #7-403

    Kihei, HI

    Kamaole Sands Unit 7-403, a spacious fourth floor (top level), 2 bedroom, 2 bath unit with a partial ocean view. Located across the street from Kamaole Beach III, this unit is great for fun-filled days and quiet evenings. All the amenities from home...

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $429/night

  25. CONDOMINIUM
    Maui Kamaole #J-110

    Maui Kamaole #J-110

    Kihei, HI

    Kamaole Beach #3 is just across from the upscale Maui Kamaole. This property features lush tropical landscaping and beautiful ocean views, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the...

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $327/night

  26. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    The Sugar Beach Resort is the perfect destination for your tropical Hawaiian getaway! This oceanfront complex is just a few steps away from Maui's longest continual white sand beach, perfect for long strolls on the beach or enjoying postcard...

    Pool Hot Tub
    FREE CANCELLATION

    $393 to $544/night

  27. CONDOMINIUM
    Haleakala Shores #A-212

    Haleakala Shores #A-212

    Kihei, HI

    Haleakala Shores A-212 is a spacious 2 bedroom 2 bath condo that is just across from Kamaole Beach III and has tropical garden views from the covered lanai. This fantastic property is within walking distance to restaurants, shops and activities....

    Pool
    FREE CANCELLATION

    $184 to $331/night

  28. CONDOMINIUM
    PuaMana 175-2

    PuaMana 175-2

    Lahaina, HI

    ~Book today and fall in LOVE with "T175-2 Puamana" You will feel like you have gone back in time to the true Hawaiian experience and all that Puamana has to offer... 175-2 Welcomes you with so much Some of the many owner-supplied extras are: •...

    Pool
    FREE CANCELLATION

    $187 to $324/night

  29. 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

  30. CONDOMINIUM
    Palm Leaf

    Palm Leaf

    Kamuela, HI

    Find outdoor living at its finest at the 2-bedroom, 2.5-bath Kulalani 104 at Mauna Lani. Several spacious, private lanais offer lush tropical views, including one with al fresco dining and a luxury outdoor kitchen with built-in stainless BBQ. With...

    Pool Hot Tub

    $238 to $598/night