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
    Wailea Ekolu Unit #312

    Wailea Ekolu Unit #312

    Wailea, HI

    Notes from the Owner: Come to relax in the luxury and tropical splendor of Maui's premier resort, Wailea. Featuring miles of pristine beaches, magnificent sunsets, and renowned cuisine, Wailea will surely be your ultimate vacation experience! The...

    Pool

    $167 to $382/night

  2. CONDOMINIUM
    Sugar Beach Resort, #330

    Sugar Beach Resort, #330

    Kihei, HI

    Unit #330 at Sugar Beach Resort is a nicely decorated third floor oceanfront unit that comes equipped with a king bed, queen sofa sleeper, 2 TV's, each with it's own DVD player, 2 cordless phones, wireless Internet, CD player, all new furniture,...

    Pool Hot Tub

    $202 to $387/night

  3. CONDOMINIUM
    Wailea Elua Unit #1305

    Wailea Elua Unit #1305

    Wailea, HI

    A note from the owner: Wailea Elua Village #1305 boasts 3 bedrooms (king bed in the master, queen bed in the 2nd bedroom and 2 twin beds in the 3rd bedroom) and a prime oceanfront ground floor location just steps from the white sands of Elua Beach....

    Pool

    $1,761 to $2,076/night

  4. CONDOMINIUM
    Sugar Beach Resort, #535

    Sugar Beach Resort, #535

    Kihei, HI

    Unit #535 is a jewel at Sugar Beach Resort. A beautiful remodel was completed in June of 2013, complete with granite counter-tops, new appliances and fun, fabulous decor. Every detail has been selected with your perfect beach vacation in mind. Very...

    Pool

    $365 to $627/night

  5. CONDOMINIUM
    Sugar Beach Resort Unit #540

    Sugar Beach Resort Unit #540

    Maui, HI

    Unit #540 at Sugar Beach Resort is a nicely decorated fifth floor oceanfront unit that comes equipped with a king bed, 1 queen, DVD player, VCR and CD/Stereo. Sugar Beach Resort is a tranquil beachfront condominium resort located in North Kihei...

    Pool

    $365 to $627/night

  6. CONDOMINIUM
    Wailea Elua Unit #1503

    Wailea Elua Unit #1503

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $459 to $953/night

  7. CONDOMINIUM
    Kihei Beach Unit #402

    Kihei Beach Unit #402

    Kihei, HI

    Kihei Beach is a moderately sized six story beachfront property located in North Kihei. It offers sweeping views of Kahoolawe, Molokini and the dazzling Pacific Ocean and a friendly casual atmosphere. Fronting the property is Sugar Beach, well known...

    Pool

    $263 to $421/night

  8. CONDOMINIUM
    Kihei Surfside, #311

    Kihei Surfside, #311

    Kihei, HI

    Kihei Surfside Resort is a unique six story oceanfront property located in South Kihei offering 180-degree views of the clear blue Pacific. The property and adjacent Keawekapu Beach together provide excellent locations for stunning sunsets,...

    Pool

    $163 to $427/night

  9. CONDOMINIUM
    Sugar Beach Resort, #130

    Sugar Beach Resort, #130

    Kihei, HI

    Unit #130 at Sugar Beach Resort is a ground floor, oceanfront condo with a newly remodeled kitchen complete with granite counter tops. This unit comes equipped with a king bed, queen size sofa sleeper, VCR, CD player and FREE wireless broadband...

    Pool Hot Tub

    $190 to $387/night

  10. CONDOMINIUM
    Kihei Beach Unit #508

    Kihei Beach Unit #508

    Kihei, Maui, HI

    Enjoy stunning views from this peaceful 5th floor condo - look out to over Sugar Beach to Maalaea Bay to views of Molokini, Lanai and Kahoolawe and regularly see whales from the lanai during whale season! This open-plan one bedroom, one bathroom...

    $185 to $309/night

  11. CONDOMINIUM
    Wailea Ekolu Unit #914

    Wailea Ekolu Unit #914

    Wailea, HI

    Wailea Ekolu Village is a tranquil terraced property located on the Wailea Blue Golf Course offering distant panoramic views of the Pacific. This quiet low-density village consists of eighteen two-story buildings spread out over 18 acres of tropical...

    Pool

    $328 to $584/night

  12. CONDOMINIUM
    Wailea Grand Champion, #180

    Wailea Grand Champion, #180

    Wailea, HI

    A note from the owner: Welcome to Grand Champions #180, our Maui getaway that comes complete with all the comforts and conveniences of home. We invite you to enjoy this 3 bedroom, 2 bath with your family and friends. You'll love the ocean view...

    Pool

    $257 to $556/night

  13. CONDOMINIUM
    Sugar Beach Resort, #121

    Sugar Beach Resort, #121

    Kihei, HI

    Unit #121 at Sugar Beach Resort is a ground floor oceanfront unit that comes equipped with a king bed, queen size sofa sleeper, DVD/VCR and CD player. Sugar Beach Resort is a tranquil beachfront condominium resort located in North Kihei offering...

    Pool Hot Tub

    $202 to $387/night

  14. CONDOMINIUM
    Sugar Beach Resort, #328

    Sugar Beach Resort, #328

    Kihei, HI

    Sugar Beach Resort is a tranquil beachfront condominium resort located in North Kihei offering sweeping views of the Pacific. There are two six story buildings with elevators and the beach fronting the property is exceptional for sunsets, swimming,...

    Pool

    $202 to $387/night

  15. CONDOMINIUM
    Kihei Beach Unit #102

    Kihei Beach Unit #102

    Kihei, HI

    Kihei Beach is a moderately sized six story beachfront property located in North Kihei. It offers sweeping views of Kahoolawe, Molokini and the dazzling Pacific Ocean and a friendly casual atmosphere. Fronting the property is Sugar Beach, well known...

    $296 to $448/night

  16. CONDOMINIUM
    Kihei Beach Unit #110

    Kihei Beach Unit #110

    Kihei, HI

    Kihei Beach is a moderately sized six story beachfront property located in North Kihei. It offers sweeping views of Kahoolawe, Molokini and the dazzling Pacific Ocean and a friendly casual atmosphere. Fronting the property is Sugar Beach, well known...

    Pool

    $263 to $421/night

  17. CONDOMINIUM
    Kamaole Nalu Unit #305

    Kamaole Nalu Unit #305

    Kihei, HI

    Kamaole Nalu Resort is a six story oceanfront property located in South Kihei. It offers time stopping views of the dazzling Pacific Ocean and a friendly casual atmosphere. Adjacent the property is Kamaole Beach, well known for it’s romantic...

    Pool

    $313 to $526/night

  18. CONDOMINIUM
    Kamaole Nalu Unit #204

    Kamaole Nalu Unit #204

    Kihei, HI

    A note from the owner: My beautiful two bedroom, two bathroom oceanfront condo is located between Kamaole 1 & 2 Beach Parks and is just steps away from the beach. Being on the 2nd floor allows for an incredible ocean view but is still close enough...

    Pool

    $246 to $394/night

  19. CONDOMINIUM
    Kihei Beach Unit #509

    Kihei Beach Unit #509

    Kihei, HI

    Kihei Beach is a moderately sized six story beachfront property located in North Kihei. It offers sweeping views of Kahoolawe, Molokini and the dazzling Pacific Ocean and a friendly casual atmosphere. Fronting the property is Sugar Beach, well known...

    Pool

    $263 to $421/night

  20. CONDOMINIUM
    Makena Surf Resort, #G-304

    Makena Surf Resort, #G-304

    Makena, HI

    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and...

    Pool

    $898 to $1,235/night

  21. CONDOMINIUM
    Royal Mauian Unit #606

    Royal Mauian Unit #606

    Maui, HI

    A note from the owner: This unit has been remodeled and has central air conditioning, LCD flat screen TVs in each room, luxury linens, kitchen supplies and more.Walks directly out to Kamaole Beach Park 1. Snorkeling is great, right in front of the...

    Pool

    $370 to $505/night

  22. CONDOMINIUM
    Kihei Surfside Unit #314

    Kihei Surfside Unit #314

    Kihei, HI

    A note from the owner: Come enjoy our newly renovated ocean front condo. We did a complete renovation in December of 2006 and it is nicely appointed with granite counter tops in the kitchen and bathrooms. You can enjoy great sunsets from the lanai...

    Pool

    $313 to $526/night

  23. CONDOMINIUM
    Royal Mauian Unit #102

    Royal Mauian Unit #102

    Maui, HI

    A note from the owner: This unit has been remodeled and has central air conditioning, LCD flat screen TVs, luxury linens, kitchen supplies, and more. Walk out directly to Kamaole Beach Park 1. Snorkeling is great right in front of the property....

    Pool

    $560 to $702/night

  24. CONDOMINIUM
    Kamaole Nalu Unit #102

    Kamaole Nalu Unit #102

    Kihei, HI

    Kamaole Nalu Resort is a six story oceanfront property located in South Kihei. It offers time stopping views of the dazzling Pacific Ocean and a friendly casual atmosphere. Adjacent the property is Kamaole Beach, well known for it’s romantic...

    Pool

    $191 to $332/night

  25. CONDOMINIUM
    Maalaea Surf Unit #f-2

    Maalaea Surf Unit #f-2

    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...

    $201 to $393/night

  26. CONDOMINIUM
    Makena Surf Resort #F-209

    Makena Surf Resort #F-209

    Kihei, HI

    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and...

    Pool

    $515 to $1,094/night

  27. CONDOMINIUM
    Hale Mahina Unit #A-201

    Hale Mahina Unit #A-201

    Lahaina, HI

    Hale Mahina Beach Resort, West Maui Hale Mahina (House of the Moon) is located on the world famous West Coast of Maui adjacent to the West Maui Mountains, nestled between Kaanapali and Kapalua in the charming oceanfront town of Honokowai. Hale...

    $358 to $560/night

  28. CONDOMINIUM
    Royal Mauian Unit #517

    Royal Mauian Unit #517

    Maui, HI

    Royal Mauian is a unique six story oceanfront property located in South Kihei offering unobstructed views of the clear blue Pacific. The property and adjacent Kamaole Beach together provide excellent locations for stunning sunsets, snorkeling,...

    Pool

    $313 to $505/night

  29. CONDOMINIUM
    Kealia Resort #102

    Kealia Resort #102

    Kihei, HI

    Unit #102 at Kealia Resort is a nicely decorated ground floor oceanfront unit that comes equipped with two queen beds and a sofa sleeper. Kealia Resort is a tranquil beachfront condominium resort located in North Kihei offering sweeping views of the...

    Pool

    $201 to $280/night

  30. CONDOMINIUM
    Wailea Ekahi Unit #22B

    Wailea Ekahi Unit #22B

    Wailea, HI

    New! For the First time in the rental pool - Gorgeous and spacious ground floor 1 bedroom / 2 bath condo, completely renovated in a contemporary style in 2017 is a 2 min walk to the world-renowned Keawakapu beach, pools and pavilion. It has walk-out...

    Pool

    $336 to $432/night