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. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Ko Olina Kai is a peaceful gated community that offers all the tranquil privacy you could desire! The interior is spacious and homey with 2 bedrooms, 2 baths, a living room with an adjacent dining space, and a kitchen. This outstanding villa offers...

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $158/night

  2. CONDOMINIUM
    Country Club Villas#115

    Country Club Villas#115

    Kailua Kona, HI

    Country Club Villas, Unit#115 is a remarkable NEW addition to the Vacation Rental Market that Knutson & Associates Property Management is proud to represent.Picture yourself living on the "Kona Country Club" golf course, be mesmerized by the...

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $244/night

  3. 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

  4. CONDOMINIUM
    Kauhale Makai 529

    Kauhale Makai 529

    Kihei, HI

    Come stay and relax at this NEWLY RENOVATED 1bd/1ba condo. This unit offers all the comforts of home with its WiFi, Cable, DVD Player, AC in the living room, and Ceiling Fans throughout. You'll also get to enjoy the fully-stocked kitchen, on-site...

    Pool Hot Tub
    FREE CANCELLATION

    $151 to $445/night

  5. CONDOMINIUM
    Kamaole Sands 5-313

    Kamaole Sands 5-313

    Kihei, HI

    Ocean and garden views close to the pool. Enjoy beautiful sunsets every evening from your private lanai in this beautifully updated third floor unit! This one bedroom (plus sleeper sofa), two bath, 818 square foot condo is ideal for families or for...

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $445/night

  6. CONDOMINIUM
    Mahana 1113

    Mahana 1113

    Lahaina, HI

    Mahana 1113, Studio Breathtaking Oceanfront Views Greet you! Sleeps 2.When you first open the door to your eleventh-floor unit, you are facing a wall of windows in your studio showcasing the panorama of the endless waves, spectacular views of the...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $1,136/night

  7. CONDOMINIUM
    Kaanapali Shores 546

    Kaanapali Shores 546

    Lahaina, HI

    This is a 5th floor residence with striking ocean and lush tropical garden views.Enjoy the refreshing breeze from your private lanai overlooking swaying palm trees, lush green landscape and the beautiful Pacific Ocean with the view of the island of...

    Pool Hot Tub
    FREE CANCELLATION

    $169 to $598/night

  8. CONDOMINIUM
    Kihei Alii Kai A101

    Kihei Alii Kai A101

    Kihei, HI

    This spacious 2 bedroom, 2 bathroom condo is fully furnished with WiFi, Cable, and A/C in the living area and master bedroom! There are also ceiling fans and floor fans throughout to help keep everything cool in the hot summer months.This unit has a...

    Pool Hot Tub
    FREE CANCELLATION

    $165 to $514/night

  9. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    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 CALENDARIf the calendar shows as available, the Villa is not reserved and can be...

    Pool Hot Tub

    $845 to $1,668/night

  10. CONDOMINIUM
    Hale Ohana Ko Olina Beach Villa (B801)

    Hale Ohana Ko Olina Beach Villa (B801)

    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

    $548 to $1,784/night

  11. CONDOMINIUM
    Nohonani #300

    Nohonani #300

    Lahaina, HI

    Nohonani 300 has recently completed a brand new renovation. Improvements include new carpeting and beautiful furnishings. This is an end unit on the third floor giving added privacy and a spectacular crows nest view of the outer islands and golden...

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $403/night

  12. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This Villa is the owner’s primary residence under section 121 of IRC. The owners offer it for rent during limited periods. As such, it is Exempt from STVR rules, so it has no STVR registration #. TAT is TA-185-465-4464-01 . Villa operates in...

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $762/night

  13. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Thoughtfully designed with your comfort in mind, Hale Nui will exceed your expectations! After a long, arduous flight, each guest will feel embraced upon entering this exquisite, spacious home and everyone will immediately marvel at the panoramic...

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  14. CONDOMINIUM
    Papakea K306

    Papakea K306

    Lahaina, HI

    A beautifully updated kitchen allows for cooking family meals in, saving money for activities and adventures. In addition to the flat screen TV and dvd player in the living room, there is also a TV in the bedroom.. Bring your electronic equipment...

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $675/night

  15. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Wonderful ocean views from this spacious penthouse level studio. The owners have completed a beautiful remodel featuring tile floors and a new sofa-sleeper. The full kitchen was recently re-done with new appliances, granite counter tops, new...

    Pool Hot Tub
    FREE CANCELLATION

    $185 to $614/night

  16. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    TROPICIAL LUXURY, ELEGANCE AND CHARM best describe this splendid 2 bedroom / 2 bath at Aina Nalu condominium. Abundant comforts await your arrival at this award winning and highly sought after Lahaina resort. You will be greeted to this 9 acre...

    Pool Hot Tub
    FREE CANCELLATION

    $189 to $645/night

  17. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Your dream Maui vacation awaits! Kamaole Sands 8-203 is on the second floor of building 8 in one of the most sought-after complexes in South Maui. This unit has been newly updated and has a brand new sofa sleeper in the living area and King mattress...

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $374/night

  18. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    The condo is totally renovated and updated. From your private lanai you have a lovely area to sit and dine or just relax with nothing but the crystal blue ocean and the famous Maui sunsets in front, FRONT SEAT WHALE WATCHING from the lanai.Tile thru...

    Pool Hot Tub
    FREE CANCELLATION

    $225 to $826/night

  19. CONDOMINIUM
    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Lahaina, HI

    Enveloped by serene gardens and detailed with stylish Asian-inspired decor, your 1BR condo combines all the comforts of home with the luxe amenities of a boutique resort. As part of the small, exclusive community at Aina Nalu, you’ll enjoy access...

    Pool Hot Tub
    FREE CANCELLATION

    $135 to $502/night

  20. CONDOMINIUM
    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    Kailua Kona, HI

    PROPERTY OVERVIEWPrime surfing and snorkeling are within steps of this 2BR/2BA condo, situated right across the street from Kahalu’u Beach. The ultra-convenient location is also close to Kona Town and Keauhou.Boasting beautiful ocean views from...

    Pool Hot Tub
    FREE CANCELLATION

    $148 to $460/night

  21. CONDOMINIUM
    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    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

    $548 to $2,016/night

  22. CONDOMINIUM
    Aina Nalu G102

    Aina Nalu G102

    Lahaina, HI

    TROPICAL LUXURY, ELEGANCE AND CHARM best describe this splendid 2 bedroom / 2 bath Aina Nalu condominium. Abundant comforts await your arrival at this award winning and highly sought after Lahaina resort. You will be greeted to this 9 acre island...

    Pool Hot Tub
    FREE CANCELLATION

    $238 to $540/night

  23. CONDOMINIUM
    Noelani #219

    Noelani #219

    Lahaina, HI

    One way to enhance an ocean view is to wrap it in lush lawns and gardens. Add to that not one, but two oceanfront pools and a Jacuzzi, and what more can you ask for? How about being as close to the ocean as you can possibly get without being on a...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $251/night

  24. CONDOMINIUM
    Kihei Alii Kai A207

    Kihei Alii Kai A207

    Kihei, HI

    Brand New Renovation! This spacious 1-bedroom, 1 bathroom condo is fully furnished and offers AC, wifi, cable, Dvd player, hairdryer, an in-unit washer and dryer, iron/ironing board, and so much more! You'll also get to enjoy the brand new sofabed...

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $456/night

  25. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    This brand-new beautiful new 5th floor listing at the Mahana at Kaanapali boasts gorgeous views of both the tranquil blue Pacific Ocean AND the lush West Maui Mountains. This property is extremely close to the water, you can literally sit in the 5th...

    Pool Hot Tub
    FREE CANCELLATION

    $438 to $1,689/night

  26. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Relax and enjoy Maui from this adorable 1bd/1ba condo!This unit offers all the comforts of home with WiFi, Cable, DVD Player, and Central AC. You'll also get to enjoy the fully-stocked kitchen, on-site laundry room, and private ocean-view and...

    Pool Hot Tub
    FREE CANCELLATION

    $130 to $451/night

  27. CONDOMINIUM
    Kaanapali Shores 725

    Kaanapali Shores 725

    Lahaina, HI

    Wonderful ocean and garden views from this spacious 2 bedroom unit . The owners have completed a beautiful remodel featuring carpeting, kitchen and bath upgrades and new furniture. The full kitchen was recently re-done with new appliances, granite...

    Pool Hot Tub
    FREE CANCELLATION

    $290 to $898/night

  28. CONDOMINIUM
    Paki Maui 123

    Paki Maui 123

    LAHAINA, HI

    Located in the front of the building, as close to the pool and ocean as you can get. At over 1200 sq feet, there is enough room to bring the whole family. Sleep 6 comfortably in our 2 bedroom 2 bath unit with full kitchen.The ocean front master...

    Pool Hot Tub
    FREE CANCELLATION

    $221 to $785/night

  29. CONDOMINIUM
    Eldorado K102

    Eldorado K102

    Lahaina, HI

    Maui Eldorado located in the beautiful Kaanapali Resort is a Golf and beach lovers delight. If you like a quiet beach, go to The Maui Eldorado cabana which is to the right of Black Rock and is the only \"on the beach\" private cabana in Maui. The...

    Pool Hot Tub
    FREE CANCELLATION

    $171 to $725/night

  30. CONDOMINIUM
    Aina Nalu G204

    Aina Nalu G204

    Lahaina, HI

    TROPICIAL LUXURY, ELEGANCE AND CHARM best describe this splendid 2 bedroom / 2 bath at Aina Nalu condominium. Abundant comforts await your arrival at this award winning and highly sought after Lahaina resort. You will be greeted to this 9 acre...

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $636/night