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.

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters
  1. CONDOMINIUM
    Kealia Resort Unit #304

    Kealia Resort Unit #304

    Kihei, HI

    Unit #304 at Kealia Resort is a nicely decorated third-floor oceanfront unit that comes equipped with a queen bed, 2 twin beds, sofa sleeper, DVD player, VCR and CD/Stereo. Kealia Resort is a tranquil beachfront condominium resort located in North...

    Pool

    $201 to $321/night

  2. 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

    $538 to $702/night

  3. 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

  4. 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

    $302 to $526/night

  5. 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

    $178 to $382/night

  6. CONDOMINIUM
    Makena Surf Resort, #G-201

    Makena Surf Resort, #G-201

    Kihei, HI

    akena 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 rocky...

    Pool Hot Tub

    $717 to $1,094/night

  7. CONDOMINIUM
    Kihei Beach Unit #203

    Kihei Beach Unit #203

    Kihei, HI

    Our second floor, oceanfront unit has a picture perfect view including Kahoolawe island, Molokini Crater, the Southwestern shoreline of Maui, and is an ideal location for whale watching (seasonal). Sugar Beach, one of the longest continuous sand...

    Pool

    $212 to $309/night

  8. 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

  9. 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

    $448 to $1,094/night

  10. CONDOMINIUM
    Wailea Elua Unit #0909

    Wailea Elua Unit #0909

    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

    $358 to $661/night

  11. 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

  12. CONDOMINIUM
    Kamaole Nalu Unit #302

    Kamaole Nalu Unit #302

    Kihei, HI

    A Note from the Owner: You will love the location on the beach and the spectacular sunsets. Numerous activities, shopping, and restaurants are all within walking distance. The beaches are a 30 second walk from the condo and the ocean and sunset...

    Pool

    $191 to $332/night

  13. 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

    $324 to $432/night

  14. CONDOMINIUM
    Kihei Beach Unit #510

    Kihei Beach Unit #510

    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

  15. CONDOMINIUM
    Kamaole Nalu Unit #403

    Kamaole Nalu Unit #403

    Kihei, HI

    Kamaole Nalu 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 its romantic sunsets, great...

    Pool

    $190 to $394/night

  16. CONDOMINIUM
    Kihei Surfside, #411

    Kihei Surfside, #411

    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

    $196 to $448/night

  17. 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

  18. CONDOMINIUM
    Makena Surf Resort, #A-101

    Makena Surf Resort, #A-101

    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

    $403 to $785/night

  19. 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

    $1,683 to $2,076/night

  20. 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

  21. CONDOMINIUM
    Royal Mauian Unit #114

    Royal Mauian Unit #114

    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

    $336 to $505/night

  22. 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

  23. 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

  24. 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

    $280 to $526/night

  25. CONDOMINIUM
    Royal Mauian Unit #202

    Royal Mauian Unit #202

    Maui, HI

    Welcome to this perfect island retreat! You will be greeted by a stunning ocean view, a spacious great room complete with two cozy couches, a reading corner and 50 inch flat screen TV and DVD player. The wall of glass offers access to the huge lanai...

    Pool

    $515 to $702/night

  26. 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

  27. 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

  28. 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

  29. 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

    $223 to $421/night

  30. 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...

    $212 to $393/night