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
    Sugar Beach Resort #PH23

    Sugar Beach Resort #PH23

    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 Hot Tub

    $202 to $387/night

  2. CONDOMINIUM
    Kamaole Nalu #603

    Kamaole Nalu #603

    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 its romantic sunsets,...

    Pool

    $223 to $394/night

  3. CONDOMINIUM
    Royal Mauian #416

    Royal Mauian #416

    Kihei, 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

    $291 to $505/night

  4. CONDOMINIUM
    Wailea Ekahi Unit #22D

    Wailea Ekahi Unit #22D

    Wailea, HI

    Wailea Ekahi Village is a beautifully terraced property located at the entrance to the resort community of Wailea. This relaxing low-density property consists of 54 two-story buildings spread out over thirty-four acres of immaculate tropical...

    Pool

    $313 to $432/night

  5. CONDOMINIUM
    Ma'alaea Surf Unit #C-8

    Ma'alaea Surf Unit #C-8

    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...

    Pool

    $257 to $526/night

  6. CONDOMINIUM
    Kihei Surfside, #309

    Kihei Surfside, #309

    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

    $167 to $427/night

  7. CONDOMINIUM
    Wailea Ekolu Unit #401

    Wailea Ekolu Unit #401

    Wailea, HI

    A Note from the Owner: We chose Maui as the prefect location for our second home based on year around outstanding weather. Every day has highs in the 80s and generally bright sunshine. Our favorite hobby is golf. There are 5 courses within a few...

    Pool

    $235 to $431/night

  8. CONDOMINIUM
    Wailea Elua Unit #0106

    Wailea Elua Unit #0106

    Wailea, HI

    About this condo: Wailea Elua Village #106 is a second floor, two bedroom-two bath, ocean view condo with a large lanai complete with a sun shade screen. It has a king bed in the master bedroom and a queen bed in the guest bedroom. This unit can be...

    Pool

    $291 to $488/night

  9. CONDOMINIUM
    Menehune Shores #425

    Menehune Shores #425

    Kihei, HI

    Menehune Shores #425 is an oceanfront ocean view unit with a gorgeous view of the ocean. It is a 2 bedroom 2 bath unit with a fully equipped kitchen, washer and dryer, and internet service. Long distance calling to the US Mainland and Canada is...

    Pool
    FREE CANCELLATION

    $208 to $347/night

  10. CONDOMINIUM
    Sugar Beach Resort, #524

    Sugar Beach Resort, #524

    Kihei, HI

    A note from the owner: Tropical bliss welcomes you from the moment you walk through the door and past the gorgeous island artwork hanging on the wall. As you step into the main living area of the condo, prepare yourself to see one of the most...

    Pool

    $202 to $387/night

  11. CONDOMINIUM
    Kihei Beach Unit #506

    Kihei Beach Unit #506

    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 $309/night

  12. CONDOMINIUM
    Kihei Surfside, #205

    Kihei Surfside, #205

    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

    $185 to $427/night

  13. CONDOMINIUM
    Kihei Beach Unit #303

    Kihei Beach Unit #303

    Kihei, HI

    A Note from the Owners: #303 is owned by Maui-lovers, and you can tell. Their unit is warm and comfortable, with a newly-remodeled kitchen equipped for the owners themselves, newly-remodeled living room and bathroom, a mosaic underwater scene from a...

    Pool

    $190 to $309/night

  14. CONDOMINIUM
    Makena Surf Resort Unit #f-212

    Makena Surf Resort Unit #f-212

    Maui, 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

    $775 to $1,094/night

  15. HOUSE
    Indo Lotus Beach House

    Indo Lotus Beach House

    Wailea, HI

    The Indo Lotus Beach House is one of the few vacation homes on Maui that has a legal grandfathered rental history, combined with a beachfront location. Set on Kamaole One Beach at the 'Charley Young' end, Indo Lotus has direct access to a popular...

    Hot Tub

    $1,458 to $2,694/night

  16. CONDOMINIUM
    Royal Mauian Unit #302

    Royal Mauian Unit #302

    Kihei, 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

    $515 to $702/night

  17. CONDOMINIUM
    Kihei Beach Unit #103

    Kihei Beach Unit #103

    Kihei, HI

    A note from the owner: We love relaxing on our sunny ground level lanai with its spectacular view of the ocean, West Maui Mountains and the Islands of Kaho'olawe, Molokini and Lanai. It feels like it is our front yard! Just a few steps across the...

    Pool

    $223 to $309/night

  18. CONDOMINIUM
    Makena Surf Resort Unit #C-103

    Makena Surf Resort Unit #C-103

    Maui, 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

    $504 to $926/night

  19. CONDOMINIUM
    Royal Mauian Unit #403

    Royal Mauian Unit #403

    Kihei, Maui, HI

    A Note from the Owner: As we look out from our lanai we are reminded that few places on earth offer the extraordinary ambiance of our Maui location - the varying colors of blue ocean, green grass near a beautiful sand beach, the sound of waves...

    Pool

    $324 to $505/night

  20. CONDOMINIUM
    Sugar Beach Resort Unit #531

    Sugar Beach Resort Unit #531

    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

  21. CONDOMINIUM
    Wailea Elua Unit #1309

    Wailea Elua Unit #1309

    Wailea, HI

    Our condo has been in our family for 25 years. The grandparents recognized the gorgeous views that Elua represented, snorkeling among the turtles, abundant sea life, great diving, fishing, and the opportunities to bike down the side of Mt....

    Pool

    $634 to $896/night

  22. CONDOMINIUM
    Makena Surf Resort, #G-101

    Makena Surf Resort, #G-101

    Makena, HI

    A note from the owner. Welcome to our Maui ohana. Our unit is special because of the extra space and privacy, including the cool, shady side lanai we call our grotto - the perfect place to curl up with a good book, and a lovely respite from the...

    Pool

    $775 to $1,094/night

  23. CONDOMINIUM
    Wailea Elua Unit #2010

    Wailea Elua Unit #2010

    Wailea, HI

    Wailea Elua Village #2010 is located on one of the buildings corners, giving you ocean views and property from the master lanai and the main lanai which may also be accessed via the guest bedroom. Recently added to the condo area large new flat...

    Pool

    $437 to $953/night

  24. CONDOMINIUM
    Wailea Elua Unit #0802

    Wailea Elua Unit #0802

    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 Hot Tub

    $459 to $953/night

  25. CONDOMINIUM
    Makena Surf Resort Unit #B-304

    Makena Surf Resort Unit #B-304

    Maui, 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

    $773 to $1,319/night

  26. 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 $336/night

  27. CONDOMINIUM
    Menehune Shores Unit #218

    Menehune Shores Unit #218

    Maui, HI

    A note from the owner: Unit 218 has been completely remodeled in 2006. It is a spacious 3 bedroom condo and is great for larger families or couples traveling together. This ocean front condo has spectacular outer island views. The condo is well...

    Pool

    $477 to $533/night

  28. CONDOMINIUM
    Kihei Beach Unit #309

    Kihei Beach Unit #309

    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...

    $263 to $421/night

  29. CONDOMINIUM
    Menehune Shores Unit #412

    Menehune Shores Unit #412

    Maui, HI

    enehune Shores is a beautiful six story oceanfront property located in North Kihei and offers unobstructed views of the clear blue Pacific. The property features an immaculately kept lawn area, a shuffleboard court, an on-site restaurant (Monsoon...

    Pool

    $230 to $303/night

  30. CONDOMINIUM
    Wailea Elua Unit #0202

    Wailea Elua Unit #0202

    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

    $494 to $1,065/night