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. APARTMENT
    Waikiki Grand 411 Studio

    Waikiki Grand 411 Studio

    Honolulu, HI

    A Sweet Freshly Remodeled & updated balcony Studio Suite next to Waikiki Beach Great View & Balcony. Recently remodeled, painted and upgraded as of November 2018 - park, zoo and ocean views from this comfortable studio with balcony - You’ll love...

    Pool
    FREE CANCELLATION

    $124 to $174/night

  2. CONDOMINIUM
    Diamond Head Beach Hotel 1401

    Diamond Head Beach Hotel 1401

    Honolulu, HI

    Legal vacation rental -  2947 Kalakaua Ave, #1401Oceanfront - Spacious 1 Bed 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...

    FREE CANCELLATION

    $360 to $557/night

  3. 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

  4. CONDOMINIUM
    Kaleialoha #214

    Kaleialoha #214

    Lahaina, HI

    Beautiful, newly remodeled 2nd floor. All new furnishings including King Bed. Brand new carpeting! Upgraded bath has tub/shower combo. Brand new queen size sofa sleeper. Ceramic stove top in open kitchen. 2nd floor on end offers privacy and...

    Pool
    FREE CANCELLATION

    $195 to $384/night

  5. 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

  6. CONDOMINIUM
    Waiohuli Beach Hale #D-214

    Waiohuli Beach Hale #D-214

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $139 to $244/night

  7. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Maui Sunset is a fabulous oceanfront property in Kihei that has lush tropical landscaping, large pool which is heated during the winter months, hot tub, gas grills, workout room, and tennis courts out on the beach for your use. Guests return here...

    Pool Hot Tub
    FREE CANCELLATION

    $167 to $254/night

  8. 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 with...

    Pool
    FREE CANCELLATION

    $358 to $375/night

  9. CONDOMINIUM
    E6-2 Bedroom Oceanfront Townhouse

    E6-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Ma'alaea Surf, Unit E6 - WHAT A VIEW! Sunsets on the lanai….Stunning views of the ocean and the West Maui Mountains…This 2 bedroom 2 bath second floor private condo sleeps 4 on comfortable Cal King beds, and is on a property built in the unique...

    Pool
    FREE CANCELLATION

    $343 to $540/night

  10. CONDOMINIUM
    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua, HI

    This elegant and upscale villa occupies the top two floors and features rare West-facing views for magnificent sunsets and 180* ocean views from your master suite! A whale watchers dream! This villa offers the best vantage of whales and their...

    Pool

    $563 to $781/night

  11. 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

    $525 to $969/night

  12. CONDOMINIUM
    Waiohuli Beach Hale #C-210

    Waiohuli Beach Hale #C-210

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool
    FREE CANCELLATION

    $208 to $347/night

  13. CONDOMINIUM
    Kapalua Bay Villa 21B2 Gold Beach Front

    Kapalua Bay Villa 21B2 Gold Beach Front

    Kapalua, HI

    This gorgeous Beach Front Villa occupies the top two floors of building 21. It has two completely private master bedrooms with en-suite. Main floor master has a private lanai. Both master suites have spectacular ocean views. There are 3...

    Pool

    $1,219 to $1,813/night

  14. CONDOMINIUM
    G9-2 Bedroom Oceanfront Townhouse

    G9-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Ma'alaea Surf, Unit G9 is a townhouse unit situated on the second floor which offers our guest total privacy. This unit has stunning ocean views and overlooks the large pool. This elegant unit features a fully furnished gorgeous kitchen and is...

    Pool
    FREE CANCELLATION

    $343 to $540/night

  15. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    The Sugar Beach Resort is the perfect destination for your tropical Hawaiian getaway! This oceanfront complex is just a few steps away from Maui's longest continual white sand beach, perfect for long strolls on the beach or enjoying postcard...

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $544/night

  16. CONDOMINIUM
    Leinaala Oceanfront #302

    Leinaala Oceanfront #302

    Kihei, HI

    Leinaala is a small 24 unit oceanfront property with panoramic views. Each unit faces the ocean. Leinaala has a relaxed and private atmosphere with a great feeling of the aloha spirit. There is an oceanfront pool, gas barbecue for your use, and...

    Pool
    FREE CANCELLATION

    $161 to $278/night

  17. CONDOMINIUM
    Surf & Racquet Club 4302

    Surf & Racquet Club 4302

    Keauhou, HI

    Recently upgraded and completely refurbished, our unique penthouse at Keauhou Surf & Racquet Club is a luxurious 3 bedroom / 2 bath unit with designer decorated furnishings , gourmet kitchen and unencumbered panoramic ocean views of the blue pacific...

    Pool
    FREE CANCELLATION

    $279 to $401/night

  18. CONDOMINIUM
    Kaleialoha #207

    Kaleialoha #207

    Lahaina, HI

    Completely remodeled condo. Two 55' Flat Screen TV's, A/C, Bosch washer Dryer, wine cooler. Granite and marble throughout. King bed. Free internet/ basic cable, onsite parking and local phone.Near Shopping, Restaurants and all beach activities....

    Pool
    FREE CANCELLATION

    $230 to $431/night

  19. 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 $448/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

    $625 to $674/night

  21. CONDOMINIUM
    Kaleialoha #315

    Kaleialoha #315

    Lahaina, HI

    Superior third floor corner unit with terra cotta tile floors, Bali teak furniture, Gourmet kitchen. Queen bed, washer/dryer, free WIFI! Recently painted and nicely updated!Near Shopping, Restaurants and all beach activities. Farmer's Market, coffee...

    Pool
    FREE CANCELLATION

    $195 to $384/night

  22. CONDOMINIUM
    Waiohuli Beach Hale #A-201

    Waiohuli Beach Hale #A-201

    Kihei, HI

    Gorgeous Remodeled Oceanfront Kihei Condo – 2BRYou can’t do better than this! Not only does this beautifully renovated second-floor unit have an unobstructed ocean view but the quality of the complex and its location cannot be beat. The ocean...

    Pool
    FREE CANCELLATION

    $288 to $604/night

  23. CONDOMINIUM
    Maui Sunset #A-509

    Maui Sunset #A-509

    Kihei, HI

    Maui Sunset – 1BR Oceanfront Condo with a Whale-Watching LanaiThere’s a reason many of our lovely guests return year after year to our oceanfront Maui condo.Actually, there are lots of reasons.The condo community’s sparkling pool which is...

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $473/night

  24. CONDOMINIUM
    Poipu Kapili 46

    Poipu Kapili 46

    Koloa, HI

    Remaining August 2019 dates now discounted!! Air-conditioned, awesome view, and newly renovated inside, in sunny Poipu with the beach just a short walk away! This comfortable 1200sf one bedroom condo is absolutely perfect for a couple looking for...

    Pool
    FREE CANCELLATION

    $275 to $361/night

  25. CONDOMINIUM
    Sealodge J9

    Sealodge J9

    Princeville, HI

    Special discount for open August dates! Our Sealodge J9 Kauai vacation rental offers dramatic and uninterrupted oceanfront views, top floor privacy, and your own furnished oceanfront lanai. Living room and both bedrooms have big picture windows...

    Pool
    FREE CANCELLATION

    $238 to $275/night

  26. CONDOMINIUM
    Sealodge D1

    Sealodge D1

    Princeville, HI

    Sealodge D1: With a private oceanfront lanai and spacious expanse of lawn in front, you'll enjoy sitting outside admiring the view and the passing chickens and nene. Take along the provided binoculars and get an up close view of the surfers, or...

    Pool
    FREE CANCELLATION

    $238 to $275/night

  27. CONDOMINIUM
    Kaleialoha 211

    Kaleialoha 211

    Lahaina, HI

    This beautiful 1 bedroom, 1 bathroom, oceanfront condominium provides everything you need for your vacation in paradise. With spectacular panoramic views over Maui’s neighbor islands, Lanai and Molokai, you can’t beat watching the whales and...

    Pool
    FREE CANCELLATION

    $175 to $335/night

  28. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Get ready for the trip of a lifetime!Royal Kahana 106 is a fantastic unit with tons of space and amazing ocean views! Equipped with cable, wifi, washer/dryer and more. You'll have all the comforts of home! Be sure to take full advantage of the lanai...

    Pool
    FREE CANCELLATION

    $165 to $494/night

  29. 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

    $271 to $749/night

  30. CONDOMINIUM
    Kahana Villa F-410

    Kahana Villa F-410

    Lahaina, HI

    F-410 is the newest, most beautifully upgraded unit around - and the prices are FANTASTIC! There is literally nothing more you could ask for in a vacation rental condo. Everything is available to you. Upgraded kitchen, granite counter tops,...

    Pool
    FREE CANCELLATION

    $206 to $291/night