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. 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

  4. CONDOMINIUM
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    We invite you to stay in our gorgeous ocean view 1 bedroom/1 bathroom condo at Honua Kai! Enjoy the sparkling blue water views from the open lanai and the bedroom, bringing a total sense of relaxation to your time in Maui. Honua Kai 346 is one of...

    Pool Hot Tub
    FREE CANCELLATION

    $338 to $919/night

  5. APARTMENT
    Waikiki Banyan Tower 1 Suite 911

    Waikiki Banyan Tower 1 Suite 911

    Honolulu, HI

    Deluxe Pool View Waikiki CondoUpgraded condo suite only one block from the world famous Waikiki Beach! Check out the view of the Diamond Head mountain range and pool from the lanai.Sleeping arrangements include a queen-sized bed and full-sized bed...

    Pool Hot Tub

    $180 to $259/night

  6. CONDOMINIUM
    Kamaole Sands #7-305

    Kamaole Sands #7-305

    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

    $157 to $365/night

  7. CONDOMINIUM
    Grand Champions #51

    Grand Champions #51

    Wailea, HI

    The nearby Ulua and Mokapu Beaches are a quick drive down the hill from the Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort. The complex offers two swimming pools,...

    Pool Hot Tub
    FREE CANCELLATION

    $244 to $358/night

  8. 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

  9. CONDOMINIUM
    Kona Makai 1-204

    Kona Makai 1-204

    Kailua Kona, HI

    This 2 bedroom 2 bath condo has everything you need to relax in paradise! Enjoy ocean views and gorgeous kona sunsets from your private lanai. The well appointed kitchen is fully equipped to comfortably prepare meals/drinks and the spacious living...

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $363/night

  10. CONDOMINIUM
    Kaanapali Shores 422 1 Bdrm

    Kaanapali Shores 422 1 Bdrm

    Lahaina, HI

    Ka'anapali Shores is located on the most desired beach on Maui, perhaps even the world! There is no greater place to unwind and relax than at this tropical oasis! Aside from the magnificent beach, the resort offers all the amenities of a AAA class...

    Pool Hot Tub
    FREE CANCELLATION

    $217 to $384/night

  11. 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

  12. CONDOMINIUM
    Papakea K-402

    Papakea K-402

    Lahaina, HI

    The ULTIMATE ISLAND getaway awaits you at our luxury 3 bedroom, 2-1/2 bath split level condo in West Maui! Our beautifully furnished condo has spectacular views of the ocean making it the perfect place to whale watch (during season) and sip...

    Pool Hot Tub
    FREE CANCELLATION

    $538 to $860/night

  13. 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

  14. CONDOMINIUM
    Country Club Villas#115

    Country Club Villas#115

    Kailua Kona, HI

    Country Club Villas, Unit#115 is a remarkable NEW addition to the Vacation Rental Market that Knutson & Associates Property Management is proud to represent. Picture yourself living on the "Kona Country Club" golf course, be mesmerized by the...

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $244/night

  15. HOUSE
    Alii Point #7 Oceanfront

    Alii Point #7 Oceanfront

    Kailua Kona, HI

    For a virtual tour of this property scroll down to the bottom of the text and click on the link. If viewing on vrbo click on the last picture and then the arrow to the right of the picture for the Virtual Tour. Private Oceanfront custom home with...

    Pool Hot Tub
    FREE CANCELLATION

    $668 to $846/night

  16. CONDOMINIUM
    Kihei Bay Vista #C-206

    Kihei Bay Vista #C-206

    Kihei, HI

    The Kihei Bay Vista is a wonderful property. It is located in Kihei Maui, just steps from the ocean. It has a pool and hot tub, gas grills for your use as well as an outdoor dining area. This property is one of the great finds for the price in...

    Pool Hot Tub
    FREE CANCELLATION

    $138 to $231/night

  17. 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

  18. 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

  19. 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

  20. 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

  21. 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

  22. 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

  23. 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

  24. 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

  25. 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

  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
    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

  28. 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

  29. 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

  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