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
    Ocean View Beachfront Beach Level 4-Bed Turtle Bay Villa 104

    Ocean View Beachfront Beach Level 4-Bed Turtle Bay Villa...

    Kahuku, HI

    Ocean View & Beachfront Beach Level 4-Bedroom (2 Masters) Turtle Bay Villa 104 At Ocean Villa 104 you have dramatic ocean views from just about everywhere! My 4-bedroom villa is located on the beach level so you can walk right out your living room...

    Pool Hot Tub

    $1,559 to $3,517/night

  2. CONDOMINIUM
    Villa 317

    Villa 317

    Kahuku, HI

    This villa is in a private location on the third floor with dramatic panoramic ocean views, just 20 yards from the ocean and just 80 yards from the sandy beach! Watch the whales swim past while in your living room during migration season! The Pool...

    Pool Hot Tub

    $515 to $920/night

  3. CONDOMINIUM
    303 Punahoa Condominium

    303 Punahoa Condominium

    Kihei, HI

    Oceanfront 1 Bedroom unit! Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. "All Units Are Non-smoking"...

    $176 to $382/night

  4. HOUSE
    Alii Point #7 Oceanfront

    Alii Point #7 Oceanfront

    Kailua Kona, HI

    For a virtual tour of this property scroll down to the bottom of the text and click on the link. If viewing on vrbo click on the last picture and then the arrow to the right of the picture for the Virtual Tour.Private Oceanfront custom home with...

    Pool Hot Tub
    FREE CANCELLATION

    $668 to $846/night

  5. HOUSE
    Ali'i Point #5 Oceanfront

    Ali'i Point #5 Oceanfront

    Kailua-Kona, HI

    Ali'i Point #5 is located at Ali'i Point, a private and gated community of 16 seaside homes with community pool and tennis court.Central A/C throughout. Main floor has living room, dining room, kitchen, half bath, and master king bedroom with en...

    Pool
    FREE CANCELLATION

    $668 to $846/night

  6. CONDOMINIUM
    Valley Isle #1106

    Valley Isle #1106

    Lahaina, HI

    From the time you open your front door a magnet pulls you across the room directly to the balcony. It takes a few swallows to get that lump cleared from your throat. This is the view you see on the travel channel, travel books, magazines, and post...

    Pool
    FREE CANCELLATION

    $156 to $251/night

  7. CONDOMINIUM
    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    Honolulu, HI

    Legal vacation rental -  2947 Kalakaua Ave, #1401Oceanfront - Spacious 1 Bed Penthouse With Large Living Area And Full Kitchen. Rooftop Penthouse - Sitting above the Pacific Ocean and nestled under Hawaii's iconic Diamond Head crater. Beautifully...

    FREE CANCELLATION

    $360 to $557/night

  8. CONDOMINIUM
    Maalaea Banyans #403

    Maalaea Banyans #403

    Maalaea, HI

    Maalaea Banyans is an ocean front condominium complex located on Maalaea Beach. Maalaea Banyans features panoramic ocean views from every unit, a swimming pool, hot tub, barbecue area, and a large oceanside lawn for sunning and relaxing. The town of...

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $371/night

  9. CONDOMINIUM
    Waiohuli Beach Hale #C-110

    Waiohuli Beach Hale #C-110

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $208 to $347/night

  10. CONDOMINIUM
    Kahana Villa F-410

    Kahana Villa F-410

    Lahaina, HI

    F-410 is the newest, most beautifully upgraded unit around - and the prices are FANTASTIC! There is literally nothing more you could ask for in a vacation rental condo. Everything is available to you. Upgraded kitchen, granite counter tops,...

    Pool
    FREE CANCELLATION

    $206 to $291/night

  11. CONDOMINIUM
    Hale Kania Kai at Surf & Racquet 3302

    Hale Kania Kai at Surf & Racquet 3302

    Kailua-Kona,, HI

    The Surf & Racquet Club located just 5 miles South of Kona town is a beautiful condominium complex situated on 16 acres of impeccably landscaped grounds and boasts a large pool, 3 professional tennis courts, covered pavillions, a vollyball court,...

    Pool
    FREE CANCELLATION

    $279 to $401/night

  12. CONDOMINIUM
    Koa Lagoon #505

    Koa Lagoon #505

    Kihei, HI

    The Koa Lagoon is an ocean front condominium complex in North Kihei with spectacular panoramic views of the Pacific ocean and Mauna Kahalawai, also known as the West Maui Mountains. Situated just 15 minutes from Kahului Airport on Sugar Beach, Koa...

    Pool
    FREE CANCELLATION

    $208 to $296/night

  13. CONDOMINIUM
    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    Kailua Kona, HI

    Lovely Oceanfront upgraded second floor 2bd2bth unit in Kona Bali Kai one of Kona's most popular oceanfront destinations. Watch the surfers at "Banyans" from your lanai at one of Kona's premier surfing spots. Light, Bright, and Airy with several...

    Pool
    FREE CANCELLATION

    $181 to $242/night

  14. CONDOMINIUM
    Hale Ono Loa 401

    Hale Ono Loa 401

    Lahaina, HI

    Look straight out from condo and large lanai directly at WHALES, SEA TURTLES, MOLOKAI & LANAI! Close to everything in West Maui! Close to Whalers and downtown Lahaina. HUGE OCEANFRONT condo complex with beautifully tiled pool, large grounds, WORLD...

    Pool
    FREE CANCELLATION

    $144 to $274/night

  15. CONDOMINIUM
    Luana Kai #C-203

    Luana Kai #C-203

    Kihei, HI

    Luana Kai is a large oceanfront complex in Kihei. It is centrally located to shops, activities and restaurants. It features a large oceanfront pool, hot tub, shuffleboard, and five gas grills for your use. There is an expansive lawn between the...

    Pool
    FREE CANCELLATION

    $128 to $219/night

  16. CONDOMINIUM
    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Ma'alaea Surf, Unit E6 - WHAT A VIEW! Sunsets on the lanai….Stunning views of the ocean and the West Maui Mountains…This 2 bedroom 2 bath second floor private condo sleeps 4 on comfortable Cal King beds, and is on a property built in the unique...

    Pool
    FREE CANCELLATION

    $343 to $540/night

  17. CONDOMINIUM
    Waiohuli Beach Hale #D-214

    Waiohuli Beach Hale #D-214

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $139 to $244/night

  18. CONDOMINIUM
    Leinaala Oceanfront #302

    Leinaala Oceanfront #302

    Kihei, HI

    Leinaala is a small 24 unit oceanfront property with panoramic views. Each unit faces the ocean. Leinaala has a relaxed and private atmosphere with a great feeling of the aloha spirit. There is an oceanfront pool, gas barbecue for your use, and...

    Pool
    FREE CANCELLATION

    $161 to $278/night

  19. CONDOMINIUM
    Waiohuli Beach Hale #C-210

    Waiohuli Beach Hale #C-210

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $208 to $347/night

  20. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Ma'alaea Surf, Unit G9 is a townhouse unit situated on the second floor which offers our guest total privacy. This unit has stunning ocean views and overlooks the large pool. This elegant unit features a fully furnished gorgeous kitchen and is...

    Pool
    FREE CANCELLATION

    $343 to $540/night

  21. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    The Sugar Beach Resort is the perfect destination for your tropical Hawaiian getaway! This oceanfront complex is just a few steps away from Maui's longest continual white sand beach, perfect for long strolls on the beach or enjoying postcard...

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $544/night

  22. CONDOMINIUM
    Surf & Racquet Club 4302

    Surf & Racquet Club 4302

    Keauhou, HI

    Recently upgraded and completely refurbished, our unique penthouse at Keauhou Surf & Racquet Club is a luxurious 3 bedroom / 2 bath unit with designer decorated furnishings , gourmet kitchen and unencumbered panoramic ocean views of the blue pacific...

    Pool
    FREE CANCELLATION

    $279 to $401/night

  23. CONDOMINIUM
    Waiohuli Beach Hale #A-201

    Waiohuli Beach Hale #A-201

    Kihei, HI

    Gorgeous Remodeled Oceanfront Kihei Condo – 2BRYou can’t do better than this! Not only does this beautifully renovated second-floor unit have an unobstructed ocean view but the quality of the complex and its location cannot be beat. The ocean...

    Pool
    FREE CANCELLATION

    $288 to $604/night

  24. CONDOMINIUM
    Maui Sunset #A-407

    Maui Sunset #A-407

    Kihei, HI

    Maui Sunset is a fabulous oceanfront property in Kihei that has lush tropical landscaping, large pool which is heated during the winter months, hot tub, gas grills, work out room and tennis courts out on the beach for your use. Guests return here...

    Pool Hot Tub
    FREE CANCELLATION

    $203 to $409/night

  25. 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

  26. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Maui Sunset – 1BR Oceanfront Condo with a Whale-Watching LanaiThere’s a reason many of our lovely guests return year after year to our oceanfront Maui condo.Actually, there are lots of reasons.The condo community’s sparkling pool which is...

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $473/night

  27. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Almost Oceanfront. Spend your vacation in a luxurious single family home within a private, gated, enclave of 16 seaside homes. This Alii Point subdivision of fine, luxury residences is a tropical paradise surrounded by a botanical garden with beach...

    Pool
    FREE CANCELLATION

    $608 to $791/night

  28. CONDOMINIUM
    Hoyochi Nikko #109

    Hoyochi Nikko #109

    Lahaina, HI

    One bedroom condo located in beautiful west Maui. For those wishing additional solitude, this is an end unit with a new queen bed and bedroom air conditioning. All units are fully equipped with Cable TV, DVD, CD player, washer/dryer, and...

    Pool
    FREE CANCELLATION

    $201 to $319/night

  29. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Maui Sunset is a fabulous oceanfront property in Kihei that has lush tropical landscaping, large pool which is heated during the winter months, hot tub, gas grills, workout room, and tennis courts out on the beach for your use. Guests return here...

    Pool Hot Tub
    FREE CANCELLATION

    $167 to $254/night

  30. CONDOMINIUM
    Luana Kai #A-103

    Luana Kai #A-103

    Kihei, HI

    Luana Kai is a large oceanfront complex in Kihei. It is centrally located to shops, activities, and restaurants. It features a large oceanfront pool, hot tub, shuffleboard, and gas grills for your use. There is an expansive lawn between the...

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $418/night