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
    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $745 to $2,016/night

  2. CONDOMINIUM
    Hale Moana Ko Olina Beach Villa (B305)

    Hale Moana Ko Olina Beach Villa (B305)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $455 to $1,268/night

  3. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    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

    $383 to $599/night

  4. CONDOMINIUM
    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    Kailua Kona, HI

    Set right across the street from Kahalu’u Beach, this 3BR/2BA condo is within steps of one of the best beaches in Hawaii for surfing. Your prime locale is also close to Kona Town and Keauhou.Perched on the second-floor, this corner unit boasts...

    Pool Hot Tub
    FREE CANCELLATION

    $216 to $517/night

  5. COTTAGE
    2BR Garden Cottage- Walk to Beach!

    2BR Garden Cottage- Walk to Beach!

    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

    $197 to $445/night

  6. CONDOMINIUM
    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Kihei, HI

    Commanding a prime location in south Kihei, this 2BR condo offers a ground-level tropical retreat with two private lanais and upscale interior upgrades including a chef’s kitchen and stylish Hawaiian decor. Enjoy access to two pools, a hot tub,...

    Pool Hot Tub
    FREE CANCELLATION

    $205 to $530/night

  7. CONDOMINIUM
    Ocean-View 2BR Kamaole Beach Royale

    Ocean-View 2BR Kamaole Beach Royale

    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

    $176 to $373/night

  8. CONDOMINIUM
    Honua Kai 210

    Honua Kai 210

    Lahaina, HI

    Come stay in our amazing Honua Kai Suite, new new sofa, new furniture and a new 49" Sam Sung ultra high DEF 4 K TV... Our beautiful one bedroom home, located on the 2nd floor of the newer, Konea building, is one of the larger 1 bedroom units at...

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $401/night

  9. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    AINA NALU C-203 Welcomes you with Aloha... C-203 is decorated with a touch of ALOHA! This is an amazing location and quality unit. Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) • Beach umbrella •...

    Pool Hot Tub
    FREE CANCELLATION

    $205 to $371/night

  10. CONDOMINIUM
    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    Lahaina, HI

    Enjoy the island breeze and ocean views from your private lanai at this spacious two-level 2BR/2BA condo. Perched on the seventh floor (the top floor) at the Kahana Villa Resort, this dreamy getaway provides lavish amenities including a shared pool,...

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $494/night

  11. CONDOMINIUM
    Hale Mahina A-403

    Hale Mahina A-403

    Lahaina, HI

    This two-bedroom, two bath has an open floor plan and gives it the feeling of a penthouse. Living room and kitchen are sunken with a large spacious deck; totally unobstructed view of the beach and ocean. The upstairs bedroom is a large loft that...

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $369/night

  12. COTTAGE
    Upgraded 2BR w/ Diamond Head Views- Walk to Beach

    Upgraded 2BR w/ Diamond Head Views- Walk to Beach

    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

    $152 to $445/night

  13. CONDOMINIUM
    Kahana Sunset C 3

    Kahana Sunset C 3

    Lahaina, HI

    The Kahana Sunset Welcomes you with This unique condo is a beachfront property on the world famous West Coast of Maui between Kaanapali and Kapalua. C-3 was completely remodeled with loads of ALOHA in 2017. Included in our fabulous price are...

    Pool
    FREE CANCELLATION

    $287 to $394/night

  14. CONDOMINIUM
    Valley Isle 110

    Valley Isle 110

    Lahaina, HI

    ~Book today and Fall in LOVE with 110 Valley iIsle The"Aloha House" You will feel like you have gone back in time to the true Hawaiian experience in this condo just STEPS from the water's edge! 110 Valley Isle Welcomes you with so much Some of...

    Pool
    FREE CANCELLATION

    $235 to $312/night

  15. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    This luxury Honua Kai one bedroom located in the 'Konea Tower' features everything you need to make your Hawaiian vacation truly enjoyable! We provide you with those extra amenities that make a difference, including comfortable beach chairs, beach...

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $401/night

  16. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 508 Welcomes you... This spacious one bedroom one bath plus den can accommodate up to six (6) guests … Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) • Beach...

    Pool Hot Tub
    FREE CANCELLATION

    $299 to $608/night

  17. CONDOMINIUM
    Hula Hideaway-303

    Hula Hideaway-303

    Lahaina, HI

    ~Book today and Fall in LOVE with "THE HULA HIDEAWAY" You will feel like you have gone back in time to the true Hawaiian experience in this condo just 10 FT from the water's edge! 303 Hula Hideaway Welcomes you with so much Some of the many...

    Pool
    FREE CANCELLATION

    $229 to $282/night

  18. HOUSE
    Ocean Tree House w/ Lanai & Yard- Walk to Beach

    Ocean Tree House w/ Lanai & Yard- Walk to Beach

    Kailua, HI

    Located in the upscale neighborhood of Lanikai, this 3BR/2BA is affectionately named Ocean Tree House and is within strolling distance to Lanikai Beach — regarded as one of the world's most beautiful top beaches, with its flour-soft white sands,...

    FREE CANCELLATION

    $485 to $803/night

  19. CONDOMINIUM
    Casa De Emdeko 338

    Casa De Emdeko 338

    Kailua-Kona, HI

    Casa De Emdeko, an oceanfront condominium complex, is located on famous Alii Drive just 1.5 miles south of Kailua Kona Village. This is a no-smoking property. Hale Makana O Ke Akua (Casa de Emdeko 338), "House of Gods Gifts", a two bedroom, two...

    Pool Hot Tub

    $251 to $409/night

  20. HOUSE
    Happy House (3-Bedroom Home)

    Happy House (3-Bedroom Home)

    Kaunakakai, HI

    Happy House is a legal vacation rental on Molokai !! Happy House- why? because staying here makes you happy! The Happy House is a three bedroom, one and one half bath oceanfront home on Kanoa Beach. Located 3.5 miles from the main town of Kaunakakai...

    FREE CANCELLATION

    $281 to $338/night

  21. TOWNHOUSE
    Ko Olina Kai Condo (1085E)

    Ko Olina Kai Condo (1085E)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $218/night

  22. TOWNHOUSE
    Keauhou Kona Surf & Racquet Club#37

    Keauhou Kona Surf & Racquet Club#37

    Kailua Kona, HI

    Knutson & Associates Property Management is proud to newly represent this wonderful 3 bedroom townhome that sleeps 6! Have a larger group? We manage the 3 bedroom townhome right next door! Townhome#36 is available within our inventory as well!!!...

    Pool
    FREE CANCELLATION

    $222 to $229/night

  23. CONDOMINIUM
    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. LIVE CALENDAR If the calendar shows as available, the property is not reserved and can...

    Pool Hot Tub

    $485 to $1,204/night

  24. CONDOMINIUM
    Hale Kaimana Ko Olina Beach Villa (B903)

    Hale Kaimana Ko Olina Beach Villa (B903)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $617 to $1,784/night

  25. CONDOMINIUM
    Hale Kai Ko Olina Beach Villa (B904)

    Hale Kai Ko Olina Beach Villa (B904)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $594 to $1,784/night

  26. CONDOMINIUM
    Oceanfront 3BR w/ Private Beach & AC

    Oceanfront 3BR w/ Private Beach & AC

    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

    $577 to $794/night

  27. CONDOMINIUM
    PuaMana 175-2

    PuaMana 175-2

    Lahaina, HI

    ~Book today and fall in LOVE with "T175-2 Puamana" You will feel like you have gone back in time to the true Hawaiian experience and all that Puamana has to offer... 175-2 Welcomes you with so much Some of the many owner-supplied extras are: •...

    Pool
    FREE CANCELLATION

    $187 to $324/night

  28. CONDOMINIUM
    2BR w/ 3 Lanais & 2 Pools, Walk to Beach

    2BR w/ 3 Lanais & 2 Pools, Walk to Beach

    Kihei, HI

    Set on a hilltop overlooking the Pacific, this beautiful 2BR/2BA offers a private beachside getaway. Your spacious condo boasts 1,279 square feet across of living space on two levels, vaulted ceilings, upgraded finishes, tropical furniture, and...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $494/night

  29. CONDOMINIUM
    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    Waikoloa, HI

    ** This home is professionally managed by TurnKey Vacation Rentals, two-time winner of the Travel Weekly Magellan Award for Vacation Rental Hospitality. With TurnKey, you can always expect exceptional service, a high-quality experience, and...

    Pool Hot Tub
    FREE CANCELLATION

    $176 to $289/night

  30. CONDOMINIUM
    Hale Leilani Ko Olina Beach Villa (B708)

    Hale Leilani Ko Olina Beach Villa (B708)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $508 to $1,384/night