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

    $371 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. CONDOMINIUM
    126 West Kuilima Dr Condo

    126 West Kuilima Dr Condo

    Kahuku, HI

    Cozy studio with loft condo. Recently remodeled full kitchen. A/C in the living room. TV with DVD. 10 minute walk from the hotel and the public beach. No WiFi. Why pay more? Welcome to Kuilima Estates, the condo property located on the grounds of...

    Pool
    FREE CANCELLATION

    $127 to $149/night

  12. 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

  13. 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

    $262 to $621/night

  14. CONDOMINIUM
    155 Wailea Ike Pl Condo Unit 123

    155 Wailea Ike Pl Condo Unit 123

    Kihei, HI

    Property Overview Situated in an exclusive gated enclave, this 3BR/2BA condo boasts $100,000 of recent upgrades. Enjoy a prime location, just seven minutes from some of the island’s best beaches. Spend days snorkeling the clear waters, or simply...

    Pool
    FREE CANCELLATION

    $342 to $812/night

  15. CONDOMINIUM
    19th Hole Turtle Bay Condo

    19th Hole Turtle Bay Condo

    Kahuku, HI

    Comfy ground floor end unit. A/C in the bedroom. Screened-in lanai with table and chairs. TV has VCR. WiFi Welcome to Kuilima Estates, the condo property located on the grounds of world-renowned Turtle Bay. The condos are surrounded by two...

    Pool
    FREE CANCELLATION

    $161 to $177/night

  16. 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

    $483 to $1,245/night

  17. 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

    $225 to $373/night

  18. 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

    $720 to $2,118/night

  19. 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

    $147 to $346/night

  20. 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

    $141 to $286/night

  21. 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

    $180 to $434/night

  22. COTTAGE
    3615 Leahi Ave Cottage Unit A

    3615 Leahi Ave Cottage Unit A

    Honolulu, HI

    Aloha! Your 2BR Honolulu cottage is so well-located, you won’t even need a car. Find yourself just down the street from the Honolulu Zoo and Aquarium and right at the edge Kapiolani Park—the largest park on Oahu. Adventurous vacationers will...

    FREE CANCELLATION

    $242 to $445/night

  23. COTTAGE
    3615 Leahi Ave Cottage Unit B

    3615 Leahi Ave Cottage Unit B

    Honolulu, HI

    Vintage Hawaiian décor—including lovely teak furniture and vibrant pops of color—welcomes you to an authentic Honolulu vacation. The 2BR configuration is perfect for a small family or friends traveling together. Within walking distance to many...

    FREE CANCELLATION

    $194 to $445/night

  24. HOUSE
    3615 Leahi Ave House

    3615 Leahi Ave House

    Honolulu, HI

    Ideal for groups who want both togetherness and privacy, this pair of vintage-inspired Hawaiian cottages are a delightful home base within walking distance to many Honolulu highlights, including legendary Waikiki Beach (20-minute walk), the Honolulu...

    FREE CANCELLATION

    $572 to $901/night

  25. CONDOMINIUM
    3823 Lower Honoa'apilani Road Condo Unit 111

    3823 Lower Honoa'apilani Road Condo Unit 111

    Lahaina, HI

    Welcome to Hale Ono Loa Napili! Relaxation comes easy at this ground-floor 1BR Lahaina condo, featuring a private ocean-view lanai and access to a shared pool. When you stay at Hale Ono Loa, you’ll have access to gas grills and a sundeck offering...

    Pool
    FREE CANCELLATION

    $154 to $262/night

  26. HOUSE
    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    This oceanfront Kohala Coast home with breathtaking coastline views offers the ultimate setting for a once-in-a-lifetime escape to paradise. Decorated in a tranquil, elegant island style, it features two master suites, central air conditioning, and...

    $1,077 to $3,202/night

  27. 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

    $970 to $2,857/night

  28. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    Kailua Kona, HI

    Among the newest additions to the exclusive Four Seasons Resort Hualalai, this ocean-view villa provides the perfect setting for a romantic getaway for two or a relaxing retreat to paradise for two couples. The villa boasts over 2,600 square feet of...

    Pool Hot Tub

    $1,056 to $3,133/night

  29. HOUSE
    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    Kamuela, HI

    This golf course-adjacent luxury home in a gated oceanfront community is the premier destination for a once-in-a-lifetime Hawaiian getaway. Offering over 3,000 square feet of island elegance with stunning views, a private pool and hot tub, and...

    Pool Hot Tub

    $1,182 to $3,374/night

  30. 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

    $1,191 to $3,571/night