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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
    Ali’i Honu Kai House

    Ali’i Honu Kai House

    Kailua-Kona, HI

    Perfectly located on the Kona “Gold Coast” of the Big Island between the charming village of Kailua~Kona and Keahou Bay, this home offers you your own personal paradise. From the moment you drive up to this dramatic gated, Ocean Front Estate you...

    Pool

    $3025 to $4840/night

  2. HOUSE
    Hanu Kai (3-Bedroom Home)

    Hanu Kai (3-Bedroom Home)

    Waimea, HI

    Tastefully designed by the Owners to create a carefree island lifestyle with beautiful sunsets year round, star gazing at its best and Whale Watching from about November through April each year.  This home offers great privacy, peaceful living and...

    $223 to $283/night

  3. CONDOMINIUM
    Honeymoon Suite

    Honeymoon Suite

    Honolulu, HI

    Welcome to the Honeymoon Suite, a "Top of the Line" 600 sq. foot unit. This oceanfront building is located in the world famous Gold Coast of Oahu. Perched high on the 12th floor of this 14-story building, this one bedroom/one bath condominium has...

    $239 to $306/night

  4. CONDOMINIUM
    Kanaloa At Kona#3701

    Kanaloa At Kona#3701

    Kailua Kona, HI

    Imagine having the privacy of your own little piece of paradise - that is exactly what you will find in this uniquely located condo. Situated at the end of the building with gorgeous ocean views over the bay, this spacious 2 bedroom 2 bath condo...

    Pool

    $140 to $511/night

  5. CONDOMINIUM
    Kona Makai 6301

    Kona Makai 6301

    Kailua Kona, HI

    One of the best ocean front locations along the Kona Coast; top level corner unit with panoramic ocean views. These oceanfront units are the most prized units in the complex.Completely remodeled 2 bedroom, 2 bath condo with an amazing wrap around...

    Pool

    $286 to $365/night

  6. HOUSE
    Sands Of Kahana 373

    Sands Of Kahana 373

    Kahana, HI

    With spectacular views of Lanai, Molokai and the West Maui coastline, this ocean front two bedroom, two bath condominium offers unique photo opportunities. Create your perfect vacation memories with sunsets, surfers, sailboats, and whales....

    Pool Hot Tub

    $315 to $368/night

  7. CONDOMINIUM
    Halii Kai #19H

    Halii Kai #19H

    Waikoloa, HI

    Welcome the newest luxury resort at the Waikoloa Beach Resort with all the features you want, but often times impossible to find on the Kohala Coast. Hali'i Kai is a direct oceanfront complex with the attributes you are looking for in your Hawaii...

    $352 to $705/night

  8. HOUSE
    Kahana Sunset A5

    Kahana Sunset A5

    Lahaina, HI

    This beautiful 2 Bedroom, 2.5 Bathroom with AC is new to our rental program! It is an oceanfront remodeled condo with spectacular views of the island of Molokai. This unit will feel like your Maui home with Hawaiiana furnishings along with upgraded...

    Pool

    $406 to $459/night

  9. CONDOMINIUM
    Pomaikai Place

    Pomaikai Place

    Honolulu, HI

    This boutique Waikiki condo faces the Hilton Hawaiian Village, it is close to bus stops, shopping, restaurants, & beaches. With a beautiful city view, and partial ocean view. Laminate wood flooring with crown molding elevates this home. The...

    Pool

    $180 to $267/night

  10. CONDOMINIUM
    Shores at Waikoloa Condo #135

    Shores at Waikoloa Condo #135

    Waikoloa Village, HI

    Shores at Waikoloa Near The Prestigious Hilton Waikoloa at Waikoloa Beach Resorts ~ 2 Bedroom, 2 Bath Private Garden Setting ~ Sleeps 6 with additional single bed in the smaller bedroom and the rollaway ~ Master BDRM-King Bed, Guest BDRM-Queen Bed...

    Pool

    $224 to $466/night

  11. CONDOMINIUM
    Palm Villas H22

    Palm Villas H22

    Waimea, HI

    Have a luxurious Big Island of Hawaii experience by staying at Palm Villas. This 2 bedroom/2 bathroom penthouse unit overlooks "The Preserve" featuring gorgeous views of the swaying palm trees and blue ocean. The home can accommodate up to 6 guests,...

    Pool

    $287 to $608/night

  12. CONDOMINIUM
    Ka'anapali Beach 2 Bedroom

    Ka'anapali Beach 2 Bedroom

    Lahaina, HI

    Ka'anapali Beach Club Just minutes from downtown Lahaina, on Maui's western shore, is Ka'anapali Beach Club Resort! Settled among lush landscaping and calming waterfalls, it is hard to not feel totally at ease when you are here. Featuring an...

    Pool Hot Tub

    $346 to $428/night

  13. CONDOMINIUM
    Kahana Sunset C5

    Kahana Sunset C5

    Lahaina, HI

    Ocean view C Building. Standard CDE rates. Two Bed Two Bath K/QT/QS. A/C throughout condo, Awning on lower lanai … Flat screen TV's throughout condo. Two sofas in living room. Tiled flooring downstairs, carpets on stairs and bedrooms. Bath tub in...

    Pool

    $262 to $315/night

  14. HOUSE
    Pele Noe

    Pele Noe

    Volcano, HI

    Pele Noe is a stunning retreat mere minutes from Volcano Village and Hawai'i Volcanoes National Park.  Nestled into a very selectively cleared native Ohia Lehua forest, everything from the site plan to the layout of the house was carefully designed...

    FREE CANCELLATION

    $166 to $195/night

  15. HOUSE
    Blue Kehena

    Blue Kehena

    Pahoa, HI

    You will be delighted as you enter this lush custom, 4 bedroom, 3 bath vacation home which was professionally designed & stylized with the taste of Hawaii. Blue Kehena features its main living space upstairs consisting of living room w/ Japanese...

    FREE CANCELLATION

    $183 to $223/night

  16. CONDOMINIUM
    Kauhale Makai #629

    Kauhale Makai #629

    Kihei, HI

    Kauhale Makaiis Hawaiian for "Village by the Sea". Kauhale Makai is an oceanfront property located in North Kihei offering ocean and garden views. It consists of two six story buildings with elevators. The beach fronting the property is excellent...

    Pool

    $160 to $372/night

  17. CONDOMINIUM
    Kauhale Makai #632

    Kauhale Makai #632

    Kihei, HI

    Kauhale Makai (Village by the Sea) is a beautiful beachfront, 169-unit condominium development in central Kihei. Unit #632 with 2 beds, 2 ensuite baths, overlooks the ocean, pool and courtyard. The Master bedroom features a King bed, the Guest...

    Pool

    $199 to $413/night

  18. CONDOMINIUM
    Sugar Beach Resort, #418

    Sugar Beach Resort, #418

    Kihei, HI

    Sugar Beach Resort is the Winner of Building of the Year and Manager of the Year Awards from the Institute of Real Estate Management (IREM®) Sugar Beach Resort is a tranquil beachfront condominium resort located in North Kihei offering sweeping...

    Pool

    $202 to $387/night

  19. CONDOMINIUM
    Menehune Shores, #623

    Menehune Shores, #623

    Kihei, HI

    Amazing Remodel Completed August 2016! New Kitchen and Bathrooms and Split-Duct Air Conditioning! See for yourself the new Menehune Shores #623! Note from the Owner: Unit 623 is on the top floor, and is referred to as a "penthouse" unit. Because...

    Pool

    $223 to $313/night

  20. CONDOMINIUM
    Kanaloa At Kona 1102

    Kanaloa At Kona 1102

    Kailua Kona, HI

    Kanaloa at Kona Resort is an oceanfront resort with 17 acres of tropical landscaping. Surrounded by the Kona Country Club and dramatic coastline. You'll never tire of walking out to see those spectacular Kona Sunsets. Guest can enjoy the heat...

    $215 to $546/night

  21. CONDOMINIUM
    Na Hale O Keauhou #N1

    Na Hale O Keauhou #N1

    Kailua Kona, HI

    Guests will not be disappointed vacationing in this exquisite 3 bedroom 3 bath town-home! Luxury at it's best, all within one of Keauhou's newest complexes conveniently located to the Keauhou Shopping center, golfing and beaches. Very spacious with...

    Pool

    $191 to $569/night

  22. CONDOMINIUM
    Kailua Bay Resort #3301

    Kailua Bay Resort #3301

    Kailua Kona, HI

    Kailua Bay Resort is located in the heart of downtown Kailua-Kona. A variety of shopping and restaurants surround the area or go grab a cold one over at Kona Brewing just down the street. This 2 bedroom/2 bathroom unit is spacious and can...

    Pool

    $114 to $317/night

  23. CONDOMINIUM
    Kona Reef #A33

    Kona Reef #A33

    Kailua Kona, HI

    Your first step inside the door begins your great Hawaiian vacation experience. The Hawaiian decor, sandy beach, oceanfront pool, spa, BBQ and a stunning sunset view from your private lanai are just the beginning! You are literally steps away from...

    Pool

    $211 to $418/night

  24. CONDOMINIUM
    Kona Makai #2101

    Kona Makai #2101

    Kailua Kona, HI

    Great location! Ground floor 2 bedroom 2 bath unit close to the ocean and pool within the desirable Kona Makai! Enjoy the easy access, and spacious open floor plan this lovely unit offers! Equipped with window A/C in the living room and both...

    Pool

    $185 to $401/night

  25. CONDOMINIUM
    Kanaloa 2201

    Kanaloa 2201

    Kailua Kona, HI

    The Kanaloa at Kona, is an exclusive 5-Star oceanfront tropical gated resort, and is the premier vacation destination in Kailua-Kona on the Big Island of Hawaii. The resort is situated on the championship Golf Course "Kona Country Club" and located...

    Pool

    $230 to $759/night

  26. CONDOMINIUM
    Kolea 16E

    Kolea 16E

    Waikoloa Village, HI

    Welcome to our hand-picked collection of luxury vacation rental properties in Kolea, a gated community located on the Big Island along the pristine white sand beaches and sheltered waters of Anaeho'omalu Bay ("A-Bay"), home to giant sea turtles and...

    Pool

    $375 to $932/night

  27. TOWNHOUSE
    Fairway Villas M3

    Fairway Villas M3

    Waikoloa Village, HI

    The Waikoloa Fairway Villas are located in an exquisite setting on the pristine private shores of King's Lake on the Waikoloa Beach Course. This luxurious villa provides a quiet and convenient location where you can enjoy the swimming pool, hot tub,...

    Pool

    $161 to $537/night

  28. CONDOMINIUM
    Hali'i Kai 15A

    Hali'i Kai 15A

    Waikoloa Village, HI

    Welcome to oceanfront living at its finest at Hali'i Kai. Hali'i Kai is a direct oceanfront complex apart of the Waikoloa Beach Resort and has all the attributes you could desire on your Big Island of Hawaii vacation. There is a large resort quality...

    Pool

    $338 to $825/night

  29. CONDOMINIUM
    Kolea 15C Penthouse

    Kolea 15C Penthouse

    Waikoloa Beach Resort, HI

    Bring friends and family on your Big Island of Hawaii vacation. This 2 bedroom/2 bathroom Penthouse is spacious and can accommodate up to 5 guests. A tropical getaway starts with where you stay, and this gated community surely has it all from an...

    Pool

    $333 to $867/night

  30. CONDOMINIUM
    Kolea 7B

    Kolea 7B

    Waikoloa Village, HI

    This beautiful vacation home with an ocean view is ideal for families or for individuals who enjoy gracious, exclusive vacation residences. Kolea Villas offers luxurious accommodations for discerning guests. With 3 bedrooms and 3 bathrooms, Kolea 7...

    Pool

    $337 to $968/night