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
    077 West Turtle Bay Condo

    077 West Turtle Bay Condo

    Kahuku, HI

    Ground Floor Unit. Light, bright, updated end unit-on first fairway. Two flat screen TVs. Maple kitchen. Tile floors. King bed. A/C in bedroom. DVD player, WIFI, computer desk. Enjoy beautiful sunsets from the lanai. 5 night minimum stay. Shower...

    Pool
    FREE CANCELLATION

    $191 to $237/night

  2. CONDOMINIUM
    1 Bedroom Corner Oceanfront 308

    1 Bedroom Corner Oceanfront 308

    Kaanapali, HI

    One Bedroom Corner - King Bed, NO sofa bed, Flat screen TV - hardwood floors; Livingroom is tiled in white. This condo will accommodate a maximum of two people. The unit has a fabulous panoramic view of the beach below and the neighboring islands....

    Pool Hot Tub
    FREE CANCELLATION

    $351 to $434/night

  3. CONDOMINIUM
    1 Bedroom Corner Oceanfront 701

    1 Bedroom Corner Oceanfront 701

    Kaanapali, HI

    Our One Bedroom Corner unit is spacious and well-appointed with a King Bed in the bedroom and a Queen sofa bed in the living room. There is seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  4. CONDOMINIUM
    1 Bedroom Corner Oceanfront 808

    1 Bedroom Corner Oceanfront 808

    Lahaina, HI

    Maui Kai unit #808 is a one Bedroom Corner - King bed; Flat screen TV; queen sofa sleeper; TV in bedroom. Beautiful one bedroom corner condo. The beach front location with its view of the ocean from our eighth floor lanai is very much like a cruise...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  5. CONDOMINIUM
    1 Bedroom Corner Oceanfront 908

    1 Bedroom Corner Oceanfront 908

    Kaanapali, HI

    This beautiful One Bedroom Corner unit was recently renovated and has a breathtaking view! Featuring a King Bed, Queen Sofa Sleeper, full kitchen, all done in the warm island style. Wake up and have breakfast on your spacious open lanai while you...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  6. CONDOMINIUM
    1 Bedroom Oceanfront 404

    1 Bedroom Oceanfront 404

    Kaanapali, HI

    One Bedroom - Flat screen TV ; King bed, 2 Twins on lanai. (No Sofa Bed) This unit located on the Kaanapali Beach less than one mile from the Kapalua West Maui Airport. This unit features an heated outdoor pool, a jacuzzi and free Wi-Fi. It...

    Pool
    FREE CANCELLATION

    $341 to $413/night

  7. CONDOMINIUM
    1 Bedroom Oceanfront 604

    1 Bedroom Oceanfront 604

    Lahaina, HI

    Maui Kai #604. One Bedroom- Flat screen TV, King Bed, Queen sofabed; TV in bedroom. This is a beautiful one bedroom sixth floor unit, with expansive views of Molokai and Lanai. Decorated luxuriously with beige tile in the entryway, kitchen and...

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  8. CONDOMINIUM
    1 Bedroom Oceanfront 804

    1 Bedroom Oceanfront 804

    Lahaina, HI

    Our One Bedroom unit is spacious and well-appointed with a King Bed in the bedroom. This condo will accommodate only two persons as there is no sofa bed. You will find seating arrangements for relaxing and dining, and there is plenty of space to...

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  9. CABIN
    1075 Nanihoku Pl Cabin

    1075 Nanihoku Pl Cabin

    Haiku, HI

    Located in the lush rainforest in the upcountry of Haiku, this unique and luxurious 2BR Asian-style bamboo bungalow includes a private hot tub and a shared freshwater pool. Boasting a custom eco-design, this rental features 1,800 sq ft of covered...

    Pool Hot Tub
    FREE CANCELLATION

    $268 to $712/night

  10. TOWNHOUSE
    1085E Ko Olina Kai Townhome

    1085E Ko Olina Kai Townhome

    Kapolei, HI

    Lovely, developer upgraded unit overlooking the greenbelt close to the tropical pool area. You will feel like you are truly in paradise, when you relax in this tropical home. The home features rich wood cabinets, granite counters, all stainless...

    Pool Hot Tub
  11. HOUSE
    1332 Mokolea Dr Home

    1332 Mokolea Dr Home

    Kailua, HI

    Located in the upscale neighborhood of Lanikai, this 3BR/2BA ocean tree house is strolling distance to Lanikai Beach — regarded as one of the world's most beautiful top beaches, with its flour-soft white sands, cooling ocean breezes, and pristine...

    FREE CANCELLATION

    $496 to $803/night

  12. CONDOMINIUM
    150 Puukolii Condo Unit 16

    150 Puukolii Condo Unit 16

    Lahaina, HI

    Property Overview  Overlooking both Lanai and Molokai, this 3BR/2.5BA condo offers the ultimate tropical getaway. Enjoy al fresco meals paired with ocean views on the private lanai or recline on lounge chairs with a refreshing beverage. Ensuring...

    Pool
    FREE CANCELLATION

    $211 to $621/night

  13. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    Offering an idyllic oceanfront setting in the town of Puako, this rental sleeps up to six guests between the 1BR cottage and a separate studio. Perfect for groups seeking extra privacy, this charming seaside compound boasts unobstructed views of the...

    FREE CANCELLATION

    $498 to $1,245/night

  14. COTTAGE
    22 Puako Beach Drive Cottage

    22 Puako Beach Drive Cottage

    Kamuela, HI

    Immerse yourself in island life at this unique 1BR oceanfront cottage. Surrounded by lush coconut palms, your rental provides unparalleled access to the turquoise water of Puako Bay and incredible ocean views from the bedroom and living area. Spend...

    FREE CANCELLATION

    $423 to $1,146/night

  15. CONDOMINIUM
    2385 S Kihei Road Condo Unit 410

    2385 S Kihei Road Condo Unit 410

    Kihei, HI

    Discover the meaning of true relaxation at this fourth-floor 2BR/2BA Kamaole Beach Royale Resort condo. Your spacious island getaway boasts incredible indoor/outdoor living space with an ocean-view lanai, as well as upscale finishes including...

    Pool
    FREE CANCELLATION

    $160 to $373/night

  16. CONDOMINIUM
    2737 S Kihei Rd Condo Unit # 4-230

    2737 S Kihei Rd Condo Unit # 4-230

    Kihei, HI

    Property Overview Situated directly across from famous Kamaole Beach III, this charming 1BR condo affords a peek-a-boo ocean view and the perfect Maui location - walking distance to excellent restaurants and a short drive to more fantastic dining...

    Pool
    FREE CANCELLATION

    $153 to $389/night

  17. CONDOMINIUM
    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai

    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai...

    Kailua Kona, HI

    An upstairs residence at Four Seasons Resort Hualalai, 2901B offers the ultimate in Big Island luxury. With amazing ocean and sunset views, central air conditioning, stylish décor, and use of a golf cart included in every rental, this villa...

    Pool

    $790 to $2,188/night

  18. CONDOMINIUM
    35 Walaka Street Condo Unit P207

    35 Walaka Street Condo Unit P207

    Kihei, HI

    The glittering ocean is at your fingertips at this tropical 1BR Kihei condo. Walk 5 minutes to the wide sands of Kamaole Beach or the waves at The Cove (one of the most popular surf breaks in South Maui) for a day of fun in the sun. Later, head back...

    Pool
    FREE CANCELLATION

    $111 to $346/night

  19. CONDOMINIUM
    3559 Lower Honoapi'ilani Road Condo Unit 2E

    3559 Lower Honoapi'ilani Road Condo Unit 2E

    Lahaina, HI

    An unforgettable Hawaii vacation is yours at this beautiful 1BR Maui Sands corner-unit condo. This condo has the highest land to condo ratio of any oceanfront condominium complex in Honokowai which means less crowds, less noise, a more peaceful...

    Pool
    FREE CANCELLATION

    $123 to $286/night

  20. CONDOMINIUM
    3559 Lower Honoapiilani Rd Condo Unit 1H

    3559 Lower Honoapiilani Rd Condo Unit 1H

    Lahaina, HI

    Relax fully at this tropical 2BR Lahaina condo at Maui Sands, with a shared pool and an excellent location within strolling distance to the beach. Gaze across the pool area from your private lanai, furnished with comfy lounge chairs and an outdoor...

    Pool
    FREE CANCELLATION

    $168 to $434/night

  21. VILLA
    3BD Fairways Villa (116C) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116C) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Make memories with family and friends in this spacious Waiulu Street ground floor villa, overlooking the 15th hole of the Jack Nicklaus Hualalai Golf Course with the Pacific Ocean and Mount Hualalai beyond. The home features an open floor plan, high...

    Pool Hot Tub

    $1,040 to $2,912/night

  22. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Relax in your own private pool and waterfall spa on a spacious deck while enjoying some of the best panoramic ocean, coastline, sunset, and Maui views in the entire Mauna Kea Resort. This exquisite luxury property, recently renovated and refreshed...

    Pool Hot Tub

    $1,261 to $3,622/night

  23. HOUSE
    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    This elegant and timeless oceanfront estate is situated on the scenic shores of beautiful Puako Bay. One of Hawaii's last remaining peaceful little beach communities, Puako is steeped in history from abundant fishing to sugar cane farming and epic...

    $1,230 to $3,526/night

  24. HOUSE
    56-419 Kamehameha Hwy Home HM- 340

    56-419 Kamehameha Hwy Home HM- 340

    Kahuku, HI

    Your charming 4BR/2BA home is just a short walk from a hidden Kahuku beach. From the updated granite kitchen to the spacious back deck and yard, this tranquil retreat offers seamless indoor and outdoor living, plus extras like boogie boards and...

    FREE CANCELLATION

    $324 to $599/night

  25. HOUSE
    6307 Kaiwiki Pl Home

    6307 Kaiwiki Pl Home

    Honolulu, HI

    Property Overview Located on a quiet cul-de-sac just minutes from the ocean, this 3BR/2BA home is perfect for a serene tropical escape. Relax on the lanai or in the private yard and enjoy meals al fresco under the tall palms. Enjoy a prime location;...

    FREE CANCELLATION

    $413 to $778/night

  26. CONDOMINIUM
    69-200 Pohakulana Place Condo #O-3

    69-200 Pohakulana Place Condo #O-3

    Waikoloa Beach Resort, HI

    Property Overview  Nestled in an inclusive enclave on the Big Island's Kohala Coast, this ground-floor condo offers the ultimate home base for your island getaway. Take in sweeping golf course views from a private lanai with al fresco dining and...

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $255/night

  27. CONDOMINIUM
    760 South Kihei Condo Unit 407

    760 South Kihei Condo Unit 407

    Kihei, HI

    Enjoy sun-soaked beach days and relaxing balmy evenings at this fourth-floor 2BR/2BA Menehune Shores condo. Your rental offers a prime location on the right side of the building, overlooking the pool and ocean. Take a dip in the heated pool, or...

    Pool
    FREE CANCELLATION

    $212 to $554/night

  28. CONDOMINIUM
    760 South Kihei Condo Unit 414

    760 South Kihei Condo Unit 414

    Kihei, HI

    Feel Pacific breezes as you unwind on the lanai of your fourth-floor 3BR/2BA condo. This unit commands the most sought-after location in the building (front and center), closest to the ocean and furthest from the road. Take in stunning wide-open...

    Pool
    FREE CANCELLATION

    $388 to $794/night

  29. CONDOMINIUM
    78-6721 ALii Dr Condo Unit 1-203

    78-6721 ALii Dr Condo Unit 1-203

    Kailua Kona, HI

    The Beach Villas represent the first new beachfront condo construction on Alii Drive in the last 20 years. This two bedroom, two bath villa is large, luxurious, designer decorated and has all the amenities you desire. You'll find ocean front views...

    Pool
    FREE CANCELLATION

    $191 to $494/night

  30. CONDOMINIUM
    78-6721 Alii Dr Condo Unit 1-203 B

    78-6721 Alii Dr Condo Unit 1-203 B

    Kailua Kona, HI

    The Beach Villas represent the first new beachfront condo construction on Alii Drive in the last 20 years. This three bedroom, two bath villa is large, luxurious, designer decorated and has all the amenities you desire. You'll find ocean front views...

    Pool Hot Tub
    FREE CANCELLATION

    $242 to $595/night