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
    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

    $99 to $844/night

  2. CONDOMINIUM
    Maui Sunset B402

    Maui Sunset B402

    Kihei, HI

    Gorgeously updated 1 bedroom with AC- right on the beach! This unit has 2 full bathrooms, a great kitchen, a lanai with ocean view. With one Queen in the bedroom, two twin pullout sleeper ottomans, a leather folding sleeper futon, and additional...

    Pool
    FREE CANCELLATION

    $150 to $453/night

  3. CONDOMINIUM
    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Ilikai Marina Condo 1290 *Legal Vacation Rental

    Honolulu, HI

    Our LEGALLY ZONED vacation rental is located at Ilikai Marina Condominiums,  1765 Ala Moana Blvd.   If you are looking for a fully equipped unit with 180 degree of ocean and beautiful Hawaiian scenery, then your search is over and you have found...

    FREE CANCELLATION

    $219 to $731/night

  4. CONDOMINIUM
    Kaleialoha 402

    Kaleialoha 402

    Lahaina, HI

    Aloha! Come stay with us at the beautiful Kaleialoha Oceanfront Resort!!This is a fully furnished Studio that sleeps 4 with everything that you will need to enjoy your paradise vacation. There is a Queen sized bed and a Queen sofa sleeper! There is...

    Pool
    FREE CANCELLATION

    $135 to $494/night

  5. CONDOMINIUM
    Lauloa 105

    Lauloa 105

    Wailuku, HI

    Start your Maui vacation off right! Watch the sun rise of Haleakala with a cup of coffee, or watch the sunset from the comfort of your lanai. See the Honu (Sea Turtles) play just outside your door or watch the surfers on the legendary surf break...

    Pool
    FREE CANCELLATION

    $194 to $438/night

  6. CONDOMINIUM
    Kapalua Bay Villas 34B-4

    Kapalua Bay Villas 34B-4

    Lahaina, HI

    The Breathtaking views from this fabulous villa is just one of the reason Kapalua is the premier spot for your Hawaiian holiday. The white sand beaches, championship golf course, award winning restaurants are just a few things to dream of before you...

    Pool
    FREE CANCELLATION

    $356 to $809/night

  7. CONDOMINIUM
    Kapalua Bay Villas 23G-2

    Kapalua Bay Villas 23G-2

    Lahaina, HI

    Hear the ocean just steps away as you enjoy the view from your vacation villa.23g2 is a luxury villa, fully furnished and beautifully renovated in 2005. Expansive, unobstructed ocean views facing Moloka'i. 1 bedroom, 1 bathroom, 1247 sq ft of living...

    Pool
    FREE CANCELLATION

    $313 to $750/night

  8. 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

    $130 to $453/night

  9. CONDOMINIUM
    Kaleialoha 203

    Kaleialoha 203

    Lahaina, HI

    Come stay with us at the beautiful Kaleialoha Oceanfront Resort!!This spacious One Bedroom one Bath condominium has all of the comforts of home. It's the perfect place for an active family vacation or a couple looking for a romantic getaway. The...

    Pool
    FREE CANCELLATION

    $158 to $578/night

  10. CONDOMINIUM
    Hale Ono Loa 106

    Hale Ono Loa 106

    Lahaina, HI

    Enjoy this West Maui Ocean Front Resort with lush grounds which includes a pool, lounge area, shuffleboard, picnic area, BBQ’s. Relax on a Lanai and enjoying sunset dinners and beautiful views of Lanai and Molokai in the distance. Maui is known...

    Pool
    FREE CANCELLATION

    $199 to $200/night

  11. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    Lahaina, HI

    This rarely-available top-floor penthouse condominium is the ultimate in luxury living. Konea 743 boasts amazing ocean views of Maui and the surrounding islands. This spacious suite includes two bedroom, two full baths and a sofa-bed to accommodate...

    Pool Hot Tub
    FREE CANCELLATION

    $513 to $988/night

  12. CONDOMINIUM
    Honua Kai- Konea 1024- One Bedroom Penthouse Ocean View! 1b/1b

    Honua Kai- Konea 1024- One Bedroom Penthouse Ocean View!...

    Kaanapali, HI

    HAPPY HOUR ON US! FREE $25 Dukes gift card for stays between 7/11/19-12/19/19. 5-night minimum, for bookings made after 7/9/19, may not be combined with any promo pricing.GREAT DEAL! TOP FLOOR - OCEAN VIEW!OCEAN VIEWS FROM ONE BEDROOM PENTHOUSE...

    Pool Hot Tub

    $316 to $1,003/night

  13. CONDOMINIUM
    Maalaea Banyans 408

    Maalaea Banyans 408

    Wailuku, HI

    Get ready for Paradise! This 3bd/2ba unit sleeps 6 and truly has an unbeatable view.Located in Maalaea, you'll be right by Haycraft Beach Park, the harbor, restaurants, shops, the aquatic center, mini golf, and so much more! You're also in the...

    Pool
    FREE CANCELLATION

    $211 to $749/night

  14. CONDOMINIUM
    Mahana 602

    Mahana 602

    Lahaina, HI

    Beautiful 6th floor studio condominium at The Mahana at Kaanapali provides everything you need for your vacation in paradise. Equipped with granite counter tops, beautiful tile floors, central A/C, WiFi, flat screen TV, stocked kitchen, and...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $750/night

  15. CONDOMINIUM
    Napili Point B5

    Napili Point B5

    Lahaina, HI

    Brand New Remodel! All new furniture throughout the condo, new flooring, new kitchen that is a dream to cook in and a brand new Split A/C system all installed September 2018.Spend the day oceanside in the comfort of cool air all year long!This is a...

    Pool
    FREE CANCELLATION

    $250 to $625/night

  16. CONDOMINIUM
    Hale Ono Loa 402

    Hale Ono Loa 402

    Lahaina, HI

    Enjoy this West Maui Ocean Front Resort with lush grounds which includes a pool, lounge area, shuffleboard, picnic area, BBQ’s. Relax on a Lanai and enjoying sunset dinners and beautiful views of Lanai and Molokai in the distance. Maui is known...

    Pool
    FREE CANCELLATION

    $219 to $225/night

  17. CONDOMINIUM
    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    Honolulu, HI

    Oceanfront - Spacious 1 Bd Penthouse With Large Living Area And Full Kitchen. Rooftop Penthouse - Sitting above the Pacific Ocean and nestled under Hawaii's iconic Diamond Head crater. Beautifully furnished with a light and airy ocean theme, this...

    FREE CANCELLATION

    $360 to $557/night

  18. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Indulge yourself in the ultimate island style luxury at the Big Island of Hawaii’s most exclusive retreat, Kauhale Pilialoha. Experience breathtaking sunsets, enjoy the natural beauty of Hawaii from the ultimate poolside lanai perched on the...

    Pool Hot Tub

    $17,975 to $27,561/night

  19. CONDOMINIUM
    Hale Mahina B401

    Hale Mahina B401

    Lahaina, HI

    Enjoy your Maui vacation from the Hale Mahina Resort!This gorgeous 2 bedroom, 2 bath, lush ocean view condo is the perfect place for couples or families looking to experience and explore the island. Equipped with a full kitchen with stainless steel...

    Pool Hot Tub
    FREE CANCELLATION

    $331 to $686/night

  20. CONDOMINIUM
    Kona Makai 6301

    Kona Makai 6301

    Kailua Kona, HI

    One of the best ocean front locations along the Kona Coast; top level corner unit with panoramic ocean views. These oceanfront units are the most prized units in the complex.Completely remodeled 2 bedroom, 2 bath condo with an amazing wrap around...

    Pool

    $286 to $409/night

  21. CONDOMINIUM
    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit A3 is a conveniently located ground floor condo, just steps from Sugar beach. This condo features a full kitchen and dining table. The master bedroom has a king sized bed. The large living room has expansive views and a flat...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  22. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    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

    $1,869 to $3,125/night

  23. CONDOMINIUM
    Kulakane 304

    Kulakane 304

    Lahaina, HI

    The Kulakane is the most distinctive condominium building on the beautiful West Maui shore with picturesque views of neighboring islands and spectacular sunsets. Watch the whales, dolphins and sea turtles up close while relaxing at our ocean side...

    Pool
    FREE CANCELLATION

    $281 to $311/night

  24. CONDOMINIUM
    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    This luxurious Island Villa is uniquely positioned to offer nice ocean views! The perfect Rx for leaving your every care behind.Surround yourself with rare exotic wood cabinetry, new granite counter tops and new stainless steel appliances,Cool...

    Pool

    $494 to $969/night

  25. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #3-203

    Keauhou Kona Surf & Racquet Club #3-203

    Kailua Kona, HI

    Keauhou Kona Surf & Racquet Club#3-203 DIRECT OCEANFRONT, 2ND FLOOR OF BUILDING#3 in complex! #3-203 is extensively upgraded & remodeled.A truly beautiful oceanfront condo in a gated complex with unobstructed ocean and Kailua town views. Elegant...

    Pool
    FREE CANCELLATION

    $216 to $327/night

  26. CONDOMINIUM
    Honua kai 437

    Honua kai 437

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 437 Welcomes you with SO MuchThis 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 towels•...

    Pool Hot Tub
    FREE CANCELLATION

    $235 to $413/night

  27. 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

  28. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-202

    Keauhou Kona Surf & Racquet Club #5-202

    Kailua Kona, HI

    BRAND NEW VACATION RENTAL WITH BRAND NEW OWNERSHIP!Welcome to #5-202 at the Keauhou Kona Surf & Racquet Club! The new owners are excited to have their new property that's never been rented before be placed as a new Vacation Rental!DIRECT OCEANFRONT...

    Pool
    FREE CANCELLATION

    $302 to $326/night

  29. CONDOMINIUM
    Polynesian Shores 111

    Polynesian Shores 111

    Lahaina, HI

    It doesn't get much better than this! Come enjoy your amazing Maui Vacation here at the breathtaking Polynesian Shores!!The perfect place for a last minute summer vacation, an upcoming trip this fall or a great spot to watch the Humpback Whales this...

    Pool
    FREE CANCELLATION

    $115 to $480/night

  30. CONDOMINIUM
    Mahana 713

    Mahana 713

    Lahaina, HI

    Beautiful 7th floor studio condominium at The Mahana at Kaanapali provides everything you need for your vacation in paradise. Equipped with granite counter tops, beautiful tile floors, central A/C, WiFi, flat screen TV, stocked kitchen, and...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $710/night