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
    Sealodge J2

    Sealodge J2

    Princeville, HI

    Amazing oceanfront views from beautiful ground floor honeymoon hideaway. Beautiful comfortable furnishings, incredible view, great ground floor location with lots of room to sit outside and enjoy the wonderful Kauai weather. New kitchen appliances....

    Pool
    FREE CANCELLATION

    $182 to $257/night

  2. CONDOMINIUM
    Maui Sands Seaside 718

    Maui Sands Seaside 718

    Lahaina, HI

    Maui Sands Seaside is located at the north end of the famous Kaanapali beach and close to the historic Lahaina town. This beautiful lush resort directly faces the sparkling blue ocean and neighboring islands of Lanai and Molokai. Swim, snorkel or...

    Pool
    FREE CANCELLATION

    $176 to $630/night

  3. CONDOMINIUM
    Kamaole Sands 05-107

    Kamaole Sands 05-107

    Kihei, HI

    Beauty and The Beach ~ Unit 5-107 is a fully remodeled, fully air conditioned ground level Condo in a lush tropical setting with a level of privacy rarely found in vacation Condo living ~ This premier Condominium home is close to all property...

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $350/night

  4. CONDOMINIUM
    Kaanapali Royal B303

    Kaanapali Royal B303

    Lahaina, HI

    Come and enjoy the Kaanapali Royal H303 2 bedroom, 2 bath condo! This beautiful and very spacious 2-bedroom condo, located in the famous Kaanapali Beach Resort area is the perfect getaway for your next Maui vacation! Just walking distance to the...

    Pool
    FREE CANCELLATION

    $274 to $575/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. HOUSE
    Kahalu'u Hale

    Kahalu'u Hale

    Kailua-Kona, HI

    This beautiful, hand-crafted, custom home, with open-beam, cedar ceilings, and air-conditioned bedrooms, is the perfect getaway vacation site. The home is located just minutes from famous Kahalu’u Beach State Park. Kahalu’u provides access to...

    Pool

    $350 to $467/night

  7. CONDOMINIUM
    126 West Kuilima Dr Condo

    126 West Kuilima Dr Condo

    Kahuku, HI

    Cozy studio with loft condo. Recently remodeled full kitchen. A/C in the living room. TV with DVD. 10 minute walk from the hotel and the public beach. No WiFi. Why pay more? Welcome to Kuilima Estates, the condo property located on the grounds of...

    Pool
    FREE CANCELLATION

    $127 to $149/night

  8. CONDOMINIUM
    Blue Hawaii 57 K Condo

    Blue Hawaii 57 K Condo

    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

    $202 to $223/night

  9. CONDOMINIUM
    Hale Kamaole #222

    Hale Kamaole #222

    Kihei, HI

    This is a Maui Vacation Rental you will enjoy the location and the ocean view. A king bed in upstairs bedroom, with newly remodeled master bath has walk in tile shower. Lower bedroom has two twins beds, loft area has queen futon. Well equipped...

    Pool
    FREE CANCELLATION

    $269 to $379/night

  10. CONDOMINIUM
    Hale Kamaole #176

    Hale Kamaole #176

    Kihei, HI

    This Ideal, Maui Vacation Rental unit #176, has it all. The owners of this condo prefer only 2 adults. Ocean & garden view garden. Completely remodeled from top to bottom in 2017. Bedroom features New King bed, 2 night stands and standing. Bedroom...

    Pool
    FREE CANCELLATION

    $196 to $318/night

  11. 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

  12. CONDOMINIUM
    Cliffs 6201

    Cliffs 6201

    Princeville, HI

    Standing on your lanai at The Cliffs #6201, you have a 180 degree unfettered view of the spectacular deep blue waters of Kauai’s northern coastline, with serene quiet only broken by the wild geese and other tropical migratory birds sailing by in...

    Pool Hot Tub

    $211 to $235/night

  13. 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
    FREE CANCELLATION

    $374 to $1,416/night

  14. HOUSE
    Sands Of Kahana 231

    Sands Of Kahana 231

    Kahana, HI

    This attractive ocean view unit on the third floor has two lanais that give you views of both the ocean and the mountains. A recent renovation of the kitchen and both bathrooms included furniture and appliance replacement. An air conditioned master...

    Pool

    $208 to $253/night

  15. CONDOMINIUM
    Ali'i Kai 2201

    Ali'i Kai 2201

    Princeville, HI

    Alii Kai 2201 provides beautiful mountain views, sunsets over Bali Hai, and a multitude of waterfalls and rainbows. The jungle is behind you and white water ocean views are just steps away. This top floor corner condo has lots of space and is a...

    Pool
    FREE CANCELLATION

    $121 to $425/night

  16. TOWNHOUSE
    Keauhou Surf & Racquet 58

    Keauhou Surf & Racquet 58

    Kailua Kona, HI

    Located on world-famous Ali'i Drive the Keauhou Kona Surf and Racquet Club is a 4-star Oceanfront Resort located 4.5 miles south of Kailua-Kona town. This gated complex is just 1/8 mile away from the Keauhou Shopping Center, which has a grocery...

    Pool

    $152 to $263/night

  17. CONDOMINIUM
    Morning Glory Fazio Condo

    Morning Glory Fazio Condo

    Kahuku, HI

    Lovely, second floor breezy, second story end unit on the 18th hole of the Fazio Golf Course.Fully equipped chef kitchen, exceptional beds and linens. Oversized washer/dryer, 3 TV's with DVD player,and A/C in living room, bedroom. WiFi. Screened in...

    Pool
    FREE CANCELLATION

    $256 to $299/night

  18. CONDOMINIUM
    Koa'e Kea's Nest

    Koa'e Kea's Nest

    Kamuela, HI

    The Fairways at Mauna Lani is a gated community of townhomes on over 20 acres in the Mauna Lani Resort. Enjoy the family style comforts of this private home. The beautiful views from your private golf course property will provide the perfect home...

    Pool

    $310 to $719/night

  19. CONDOMINIUM
    Sealodge G8

    Sealodge G8

    Princeville, HI

    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 house at Kilauea....

    Pool
    FREE CANCELLATION

    $203 to $275/night

  20. CONDOMINIUM
    Kaanapali Shores 819

    Kaanapali Shores 819

    LAHAINA, HI

    This beautiful 1-bedroom, 1-bathroom oceanfront condominium provides everything you need for your vacation in paradise. With spectacular views of the ocean from the 8th floor and a spanning view of the beautiful resort, you can’t beat the view...

    Pool
    FREE CANCELLATION

    $206 to $406/night

  21. CONDOMINIUM
    Maui Kai 206

    Maui Kai 206

    Lahaina, HI

    Enjoy unbeatable panoramic views from this highly desirable 2nd floor oceanfront unit on the Kaanapali coast. You can’t get any closer to the ocean than this resort! Watch gorgeous sunsets over Molokai & Lanai every day from the comfort of your...

    Pool
    FREE CANCELLATION

    $156 to $500/night

  22. CONDOMINIUM
    Papakea Condominium K306

    Papakea Condominium 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

    $196 to $659/night

  23. 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

    $169 to $639/night

  24. VILLA
    Ridge1112 Ocean View

    Ridge1112 Ocean View

    Kapalua, HI

    Enjoy 5 star accommodations in an exclusive private villa paradise! Custom Designed and Fully Upgraded Ridge Villa with Ocean Views from Every Room! Designed from the onset to take advantage of its unique Island setting, Kapalua Ridge Villa 1112 is...

    Pool

    $494 to $869/night

  25. VILLA
    Ridge 2614 Gold

    Ridge 2614 Gold

    Kapalua, HI

    Breathtaking ocean vistas will amaze you from the moment you arrive. This palatial Kapalua Ridge Villa offers the perfect setting for families or couples. Spacious and elegantly designed, surrounded by lush tropical landscape and endless ocean...

    Pool

    $519 to $869/night

  26. VILLA
    Ridge 1523 Gold Ocean View

    Ridge 1523 Gold Ocean View

    Kapalua, HI

    Each luxurious master suite has ocean views and a private lanai. The private baths are spa quality and rich with every creature comfort. The furnishings are top of the line and designed for beauty and comfort. The kitchen is well equipped and...

    Pool

    $531 to $906/night

  27. VILLA
    Bay Villa 32B3 Gold Ocean View

    Bay Villa 32B3 Gold Ocean View

    Lahaina, HI

    Spectacular views of the Pacific and the neighboring island of Molokai. Magnificent painted sky at dusk and dawn will take your breath away! Perfectly positioned to allow warm tropical breezes and gentle sounds of surf fill every room. This...

    Pool

    $369 to $594/night

  28. VILLA
    Bay Villa 30B1 Gold Ocean Front

    Bay Villa 30B1 Gold Ocean Front

    Kapalua, HI

    This unique oceanfront location is situated on one of the most beautiful parts of the West Maui coast, Fresh out of renovation and rich with every imaginable upgrade. Every surface has been covered in natural stone, glass tile and rich exotic woods....

    Pool

    $563 to $781/night

  29. VILLA
    Ridge 1511 Gold Ocean View

    Ridge 1511 Gold Ocean View

    Kapalua, HI

    This lovely villa is a feast for the eyes. You will feel the weight of the world dissolve as you enter this island paradise. This is a true 5 star experience! You'll be tempted not to leave the luxury of this well appointed villa. Every creature...

    Pool

    $294 to $494/night

  30. VILLA
    Ridge 611Ocean View

    Ridge 611Ocean View

    Kapalua, HI

    Beauty surrounds you in this lovely 1 bedroom 2 bath split level villa. One of few with an ocean view from the master suite! While you will feel nestled in and pleasantly secluded. You are only a short 4 minute walk to the beach and just steps from...

    Pool

    $269 to $494/night