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
    Ko Olina Beach Villa (O425)

    Ko Olina Beach Villa (O425)

    Kapolei, HI

    LIVE CALENDAR If the calendar shows as available, the property is not reserved and can be booked instantly online. This listing is updated in real-time. Please click the calendar tab to see availability. This Villa requires a minimum 6 night stay....

    Pool

    $485 to $1,204/night

  2. CONDOMINIUM
    Honua Kai 506

    Honua Kai 506

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 506 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

    $311 to $608/night

  3. VILLA
    Bay Villa 22G2 Gold Ocean Front

    Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Perfectly situated above the waves in the most pristine and highly desired locations in Kapalua! This unique floor plan is the only ground-floor Kapalua Bay villas that can boast an additional 150+ square feet of living space facing the ocean!!...

    Pool

    $813 to $1,219/night

  4. VILLA
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    This brand new upscale luxury condo is located in the privately gated new Waikoloa Beach Villas Complex, close to the activity center with two pools, fitness workout room and spa areas. The complex is located in the best area of the entire Waikoloa...

    Pool
    FREE CANCELLATION

    $258 to $506/night

  5. CONDOMINIUM
    Honua Kai 437

    Honua Kai 437

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 437 Welcomes you with SO Much This spacious studio, 1 bath can accommodate up to 4 guests. Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) • Beach umbrella • Beach...

    Pool Hot Tub
    FREE CANCELLATION

    $264 to $413/night

  6. HOUSE
    Papaua Estate

    Papaua Estate

    Lahaina, HI

    APPROVED MAUI SHORT TERM RENTAL HOUSE #STWM 2104/0003. You and your family and friends will love your stay here for a vacation filled with Aloha! If you are looking for location, luxury and Hawaiian life style, you have found it. Perhaps the most...

    Hot Tub
    FREE CANCELLATION

    $2,119 to $3,125/night

  7. CONDOMINIUM
    New! Updated! Modern, Maui Beachfront with Central A/C

    New! Updated! Modern, Maui Beachfront with Central A/C

    Lahaina, HI

    Most frequently asked questions re: payments, cancellations, our home, and the area, can be answered in the property info, guest reviews, and pictures, below. We kindly ask that you read all of these details, as we offer a lot of amenities that...

    Pool Hot Tub
    FREE CANCELLATION

    $561 to $731/night

  8. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    AINA NALU A-201 Welcomes you with Aloha... This unique condo in the heart of Old Lahaina Town is a perfect vacation spot! A-201 was completely remodeled with the touch of ALOHA in 2016. Included in our fabulous price are many owner-supplied extras...

    Pool Hot Tub
    FREE CANCELLATION

    $205 to $371/night

  9. CONDOMINIUM
    Kamaole Sands #1-103

    Kamaole Sands #1-103

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Kamaole Sands is located across the street from Kamaole Beach III. Whale watch, swim, snorkel, walk miles on the beach and watch the most amazing sunsets imaginable. There are 15 acres of lush...

    Pool
    FREE CANCELLATION

    $168 to $278/night

  10. TOWNHOUSE
    Keauhou Surf & Racquet 58

    Keauhou Surf & Racquet 58

    Kailua Kona, HI

    Located on world-famous Ali'i Drive the Keauhou Kona Surf and Racquet Club is a 4-star Oceanfront Resort located 4.5 miles south of Kailua-Kona town. This gated complex is just 1/8 mile away from the Keauhou Shopping Center, which has a grocery...

    Pool

    $152 to $263/night

  11. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    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 $370/night

  12. 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 many...

    Pool
    FREE CANCELLATION

    $287 to $406/night

  13. 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

    $241 to $282/night

  14. CONDOMINIUM
    Honua Kai 508

    Honua Kai 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

    $311 to $608/night