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
    Turtle Bay Sunset Retreat***TA-188332646401

    Turtle Bay Sunset Retreat***TA-188332646401

    Kahuku, HI

    Beautiful second story upgraded condo in a great location! Close to the beach, the hotel and LeiLeis restaurant. 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

    $225 to $271/night

  2. ESTATE
    Kailua Shores Estate

    Kailua Shores Estate

    Kailua, HI

    One of the largest, most private and secluded Estates on the island of Oahu. A spectacular beachfront location-at Kailua Shores Estate with the comfort of a resort, consisting of separate houses, newly remodeled, set on extensive grounds featuring a...

    Pool

    $7,860 to $12,620/night

  3. CONDOMINIUM
    Kamaole Nalu Unit #604

    Kamaole Nalu Unit #604

    Kihei, HI

    Kamaole Nalu Resort is a six story oceanfront property located in South Kihei. It offers time stopping views of the dazzling Pacific Ocean and a friendly casual atmosphere. Adjacent the property is Kamaole Beach, well known for it's romantic...

    $259 to $459/night

  4. CONDOMINIUM
    Grand Champions #45

    Grand Champions #45

    Wailea, HI

    The nearby Ulua and Mokapu Beaches are a quick drive down the hill from the The Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort. The complex offers two swimming...

    Pool Hot Tub
    FREE CANCELLATION

    $261 to $400/night

  5. CONDOMINIUM
    Luana Kai #A-103

    Luana Kai #A-103

    Kihei, HI

    Luana Kai is a large oceanfront complex in Kihei. It is centrally located to shops, activities, and restaurants. It features a large oceanfront pool, hot tub, shuffleboard, and gas grills for your use. There is an expansive lawn between the...

    Pool Hot Tub
    FREE CANCELLATION

    $255 to $406/night

  6. CONDOMINIUM
    Luana Kai #C-203

    Luana Kai #C-203

    Kihei, HI

    Luana Kai is a large oceanfront complex in Kihei. It is centrally located to shops, activities and restaurants. It features a large oceanfront pool, hot tub, shuffleboard, and five gas grills for your use. There is an expansive lawn between the...

    Pool
    FREE CANCELLATION

    $128 to $219/night

  7. CONDOMINIUM
    338

    338

    Kihei, HI

    This Colorful two bedroom Maui condo features ocean, garden, and pool views! Kitchen has been remodeled with tile floors, new cabinets and is equip with all of your cooking essentials while visiting. Unit has a full washer/dryer. Living room has...

    Pool
    FREE CANCELLATION

    $235 to $346/night

  8. CONDOMINIUM
    266

    266

    Kihei, HI

    Beautiful Ocean & mountain views and just steps away from the family friendly Kamaole Beach III. This top floor condo with two bedrooms and loft, has recently been updated with new carpeting and new paint. Master bedroom has a new king bed,...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  9. CONDOMINIUM
    264

    264

    Kihei, HI

    Great Ocean and mountain Views. Two bedroom with loft. Upstairs master bedroom has king bed, downstairs bedroom has two twin beds, with queen hide-a-bed in living room. Loft has twin bed. Kitchen and Bathrooms have new cabinets. Bathrooms provide...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  10. CONDOMINIUM
    326

    326

    Kihei, HI

    Beautifully updated condo with partial Ocean View! Upstairs master bedroom has island style King bed and furniture. Remodeled master bath has walk-in tiled shower, new vanity and granite top. Downstairs bedroom has island style furniture with 2 Twin...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  11. CONDOMINIUM
    221

    221

    Kihei, HI

    Two bedroom with a great Ocean View. Large clay tiles from front door to lanai. Decorated by interior designer, color and style pleasing to the eye. Beautiful furniture, comfy sofa with queen hide-a-bed. Bedroom decor very Hawaiian with dark wood...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  12. CONDOMINIUM
    308

    308

    Kihei, HI

    Fantastic ocean & mountain view in this Maui Vacation Rental. New Carpet and tile shower installed. Master bedroom and loft area have queen beds. Downstairs bedroom has two twins. Queen hide-a-bed in the living room, along with 2 sitting chairs. New...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  13. CONDOMINIUM
    311

    311

    Kihei, HI

    This two bedroom condo without a loft, has a good Ocean and Garden View. Master bedroom has king bed. Down stairs bedroom has king bed. Hide a bed couch in the living room. Spacious kitchen cabinets. Wood and tile floor including lanai no carpet....

    Pool
    FREE CANCELLATION

    $235 to $346/night

  14. CONDOMINIUM
    340

    340

    Kihei, HI

    Ocean and Garden Views. This two bedroom with loft has been remodeled with tile installed from the entrance to the lanai. Tile walk-in shower in downstairs bathroom. Both Bathrooms’ cabinets and counter tops have been recently remodeled. Master...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  15. CONDOMINIUM
    Kona Reef D32

    Kona Reef D32

    Kailua Kona, HI

    Private, top floor, absolute oceanfront, lovely one bedroom condo at the highly acclaimed Kona Reef Resort! Why Kona Reef: • Conveniently located along the prestigious Alii Drive in the heart of Kona town. • It’s a 5 minute walk in your...

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $292/night

  16. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #6-104

    Keauhou Kona Surf & Racquet Club #6-104

    Kailua Kona, HI

    **BRAND NEW PROPERTY IN OUR INVENTORY! AIR CONDITIONING INSTALLED AS OF SEPTEMBER 2018!** Unit#6-104 is a well-maintained 2BR/2BA ground floor unit in a 15-acre, gated oceanfront complex at the Keauhou Kona Surf & Racquet Club. It's also an end...

    Pool
    FREE CANCELLATION

    $256 to $292/night

  17. TOWNHOUSE
    Keauhou Kona Surf & Racket Club Townhouse #4

    Keauhou Kona Surf & Racket Club Townhouse #4

    Kailua Kona, HI

    Looking to stay direct oceanfront & within steps to the beach? Look no further, you've found the perfect property! Welcome to the page of our direct oceanfront, townhome#4 at the Keauhou Kona Surf & Racquet Club. We're extremely proud to be newly...

    Pool
    FREE CANCELLATION

    $428 to $447/night

  18. CONDOMINIUM
    Royal Sea Cliff #704

    Royal Sea Cliff #704

    Kailua Kona, HI

    ENJOY UPSCALE PENTHOUSE LIVING AT THIS FULLY FURNISHED OCEAN FRONT LUXURY RESORT CONDOMINIUM COMPLEX IN KONA! Breathtaking white water views, marble floors, soaring ceilings, spacious tiled lanai with wet bar, upgraded cabinetry and countertops...

    Pool Hot Tub
    FREE CANCELLATION

    $353 to $467/night

  19. CONDOMINIUM
    Casa De Emdeko 111

    Casa De Emdeko 111

    Kailua Kona, HI

    Casa#111 is an excellent ground floor unit, that's VERY spacious! Nearly 1300 square feet! Close to the pool for easy access. There are new owners who own the property! Wifi! Casa De Emdeko offers owners and guests the perfect blend of Hawaiian...

    Pool
    FREE CANCELLATION

    $309 to $323/night

  20. CONDOMINIUM
    Kona Makai 1-301

    Kona Makai 1-301

    Kailua Kona, HI

    Kona Makai #1-301 is arguably the BEST condo in the entire complex! Being the top floor corner in building 1, the location is undeniably too perfect. Private & upgraded, this is direct oceanfront condo living at its finest. You can't get a better...

    Pool Hot Tub
    FREE CANCELLATION

    $626 to $674/night

  21. CONDOMINIUM
    Kona Plaza#220

    Kona Plaza#220

    Kailua Kona, HI

    Welcome to the listing page of Kona Plaza#220! It's amazing location puts you right in immediate walking distance to restaurants, beaches, shopping & entertainment right in the heart of Kailua Village. This comfortable 1 bedroom, 1 bath that sleeps...

    Pool
    FREE CANCELLATION

    $139 to $211/night

  22. CONDOMINIUM
    Kona Isle D21

    Kona Isle D21

    Kailua Kona, HI

    Stunning direct oceanfront views in this gorgeous one bedroom will make you never want to leave.The rhythmic sounds of crashing waves generated by the nearby Pacific Ocean provide a serene soundtrack to peaceful meals from the lanai, which overlooks...

    Pool
    FREE CANCELLATION

    $111 to $146/night

  23. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #3-101 "Hale Malama Pono"

    Keauhou Kona Surf & Racquet Club #3-101 "Hale M...

    Kailua Kona, HI

    Welcome to Hale Malama Pono, a temporary home base for you to enjoy what Hawaii has to offer you as a visitor while treading as lightly as you can. Your hosts are long time visitors to the Island and now new owners. This home away from home is...

    Pool
    FREE CANCELLATION

    $292 to $350/night

  24. TOWNHOUSE
    Keauhou Kona Surf & Racquet Club #176

    Keauhou Kona Surf & Racquet Club #176

    Kailua Kona, HI

    **Brand new Property in our Vacation Rental Inventory, that we're proud to represent!!** **TAKE A VIRTUAL TOUR OF THE PROPERTY! -If link is not shown, please inquire within! This is a gorgeous ocean front townhouse corner unit. Being an end unit...

    Pool
    FREE CANCELLATION

    $360 to $375/night

  25. CONDOMINIUM
    Casa De Emdeko 204

    Casa De Emdeko 204

    Kailua Kona, HI

    Casa 204 is an excellent, affordable 2nd floor property that you will certainly love. Unit#204 has been NEWLY REMODELED IN APRIL 2019! All new flooring, furniture, kitchen, bathrooms, paint, appliances! Central AC, WIFI, Elevators, Beach gear! Look...

    Pool
    FREE CANCELLATION

    $165 to $239/night

  26. CONDOMINIUM
    Hale Ono Loa 401

    Hale Ono Loa 401

    Lahaina, HI

    Look straight out from condo and large lanai directly at WHALES, SEA TURTLES, MOLOKAI & LANAI! Close to everything in West Maui! Close to Whalers and downtown Lahaina. HUGE OCEANFRONT condo complex with beautifully tiled pool, large grounds, WORLD...

    Pool Hot Tub
    FREE CANCELLATION

    $144 to $274/night

  27. CONDOMINIUM
    Kaanapali Shores Studio 742

    Kaanapali Shores Studio 742

    Lahaina, HI

    Enjoy the luxuries of home with this studio unit. You will enjoy partial ocean views from within the unit as well as from the lanai! You will also view the gorgeous West Maui Mountains from this highly desirable corner unit! The kitchen and...

    FREE CANCELLATION

    $186 to $359/night

  28. CONDOMINIUM
    Kuhio Village Condominium 1101A *Legal Vacation Rental

    Kuhio Village Condominium 1101A *Legal Vacation Rental

    Honolulu, HI

    Our LEGALLY ZONED vacation rental is located at Kuhio Village Towers, 2463 Kuhio Avenue.        Two short blocks to the World's most famous beach. Wake up and enjoy beautiful ocean views and tropical breezes from your eat-in kitchen or spacious...

    FREE CANCELLATION

    $107 to $596/night

  29. CONDOMINIUM
    Kuhio Village 1205 Condominium

    Kuhio Village 1205 Condominium

    Honolulu, HI

    Queen size bed, private balcony, partial ocean views 2 Blocks from Waikiki beach Penthouse Top Floor level and Location! Location! Location! Central Waikiki, top floor furnished studio suite with Private lanai and partial ocean view. Queen size...

    FREE CANCELLATION

    $126/night

  30. CONDOMINIUM
    Hale Ko'aniani (Sea Village 4107)

    Hale Ko'aniani (Sea Village 4107)

    Kailua-Kona, HI

    This unit sets the stage for casual vacation fun! Two bedrooms, two bath condo sleeps 4 comfortably. This truly oceanfront unit features a bright and cheery atmosphere. Cook dinner while watching the Pacific! Beautiful wood flooring throughout...

    Pool Hot Tub

    $169 to $304/night