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. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    This large 2 bedroom/ 2 bath home has enormous square footage, vaulted bamboo ceilings and a huge wrap around deck. New furnishings, top of the line appliances, gourmet kitchen and so much more… Newly installed A/C and many ceiling fans make it a...

    FREE CANCELLATION

    $471 to $683/night

  2. 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

    $158 to $596/night

  3. 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

  4. CONDOMINIUM
    Maui Eldorado D200- 2 Bedroom Ocean View

    Maui Eldorado D200- 2 Bedroom Ocean View

    Kaanapali, HI

    LIGHT & BRIGHT CORNER 2 BEDROOM!!!Beautiful 1,440 Sq ft 2 bedroom/2bath condo with Peek-a-boo Ocean View!What a find! The oversized covered lanai of this second floor, end location is the perfect spot to relax after a long day of Whale Watching,...

    Pool Hot Tub

    $310 to $1,017/night

  5. CONDOMINIUM
    Sandpiper 121B

    Sandpiper 121B

    Princeville, HI

    Special discount for open August dates! Sandpiper 121B is a perfect choice for couples seeking a romantic getaway on a budget! The private garden-level lanai is surrounded by tropical foliage and flowers. This charming studio has a private bathroom...

    Pool Hot Tub
    FREE CANCELLATION

    $115 to $153/night

  6. 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

  7. CONDOMINIUM
    Honua Kai- Hokulani 509- Ocean view from INSIDE! 2b/2b

    Honua Kai- Hokulani 509- Ocean view from INSIDE! 2b/2b

    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.Hokulani #509 is located in one of the most desirable stacks on the entire...

    Pool Hot Tub

    $580 to $1,839/night

  8. CONDOMINIUM
    Kapalua Bay Villas 17B-3

    Kapalua Bay Villas 17B-3

    Lahaina, HI

    Main living area comfortably accommodates you and your guests for lounging around while taking in the views having a afternoon snack at the bar top or sitting down to a meal in the dining area.2 full bathrooms, one on each floor of this 2 level...

    Pool
    FREE CANCELLATION

    $344 to $1,000/night

  9. CONDOMINIUM
    Wailua Bay View 204

    Wailua Bay View 204

    Kapaa, HI

    This air conditioned east shore Kauai vacation rental on the Royal Coconut Coast at Wailua Bay View 204 is perfect for your romantic getaway. The beach is right in front. Literally right in front. You've got a perfect beach and ocean view that...

    Pool
    FREE CANCELLATION

    $238 to $257/night

  10. CONDOMINIUM
    Sealodge J1

    Sealodge J1

    Princeville, HI

    Sealodge J1: Private, quiet and serene with oceanfront views all the way down the Anini Reef to the Kilauea lighthouse. On the edge of the bluff between the trees and the ocean, this condo sits alone like a separate little house, facing the sea....

    Pool
    FREE CANCELLATION

    $238 to $275/night

  11. 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

    $176 to $498/night

  12. TOWNHOUSE
    Keauhou Kona Surf & Racquet Club#37

    Keauhou Kona Surf & Racquet Club#37

    Kailua Kona, HI

    Knutson & Associates Property Management is proud to newly represent this wonderful 3 bedroom townhome that sleeps 6!Have a larger group? We manage the 3 bedroom townhome right next door! Townhome#36 is available within our inventory as...

    Pool
    FREE CANCELLATION

    $222 to $229/night

  13. 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

  14. 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

    $260 to $361/night

  15. HOUSE
    1 Bedroom Corner Oceanfront #908

    1 Bedroom Corner Oceanfront #908

    Kaanapali, HI

    This beautiful One Bedroom Corner unit was recently renovated and has a breathtaking view! Featuring a King Bed, Queen Sofa Sleeper, full kitchen, all done in the warm island style. Wake up and have breakfast on your spacious open lanai while you...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  16. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    TVNCU-1343 - TA# 127-070-6176-01 Hale Ola Kai is a three bedroom, two and a half bath home located near world famous Hanalei Bay. The house is a comfortable family-style home. Casual, yet equipped with anything you need to make your stay in Hanalei...

    FREE CANCELLATION

    $475 to $653/night

  17. VILLA
    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    Waikoloa, HI

    Stay in our lovely 2 Bedroom 2 Bath villa overlooking the lake located in the Waikoloa Resort area. This Fairway Villa Unit is only 25 miles from Kona and 18 miles north of the airport. You will be minutes away from some of the world's best rated...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $407/night

  18. CONDOMINIUM
    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    Waikoloa, HI

    Enjoy our 2 bedroom / 2 bath home for you and your family quietly tucked away along the Big Island's sunny Kohala Coast, Fairway Villas Waikoloa offers the crisp style, gracious elegance, and modern sophistication. The master bedroom has a king bed...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $407/night

  19. 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 $186/night

  20. CONDOMINIUM
    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    Kihei, HI

    Maalaea Surf, Unit A5 is a townhouse unit on the second floor which offers our guest total privacy and is located beach front on the property. This loft suite with 2 baths is very well furnished.Enjoy ocean front outdoor living on your spacious...

    FREE CANCELLATION

    $304 to $467/night

  21. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    We welcome you to stay at our private luxury home (Ono Hale) in the lush hills above historic Kailua Kona. Located just minutes from town and Kona’s beautiful sandy beaches.Cool and quiet. Ono Hale is situated on a very private lot on a quiet...

    Pool
    FREE CANCELLATION

    $525/night

  22. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    The Kahana Sunset Welcomes you withThis unique condo is a beachfront property on the world famous West Coast of Maui between Kaanapali and Kapalua.Included in our fabulous price are many owner-supplied extras such as:• Beach chairs (2)• Beach...

    Pool
    FREE CANCELLATION

    $223 to $389/night

  23. 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

  24. COTTAGE
    International Colony Club 34

    International Colony Club 34

    Lahaina, HI

    -Enjoy this charming Hawaiian Plantation Style cottage just a short walk to beautiful Kahekili Beach Park also known as Airport Beach. Lush landscapes and Plumeria trees bursting with flowers all all around!-10 PM quiet time rules apply at this...

    Pool
    FREE CANCELLATION

    $224 to $415/night

  25. CONDOMINIUM
    Napili Shores D230

    Napili Shores D230

    Lahaina, HI

    Come Stay at the famous Napili Shores in this spacious remodeled garden view studio!Beautiful Plumeria trees just off of your private lanai line the interior of this very popular vacation property. This studio comes with a wonderful fully stocked...

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $299/night

  26. 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

  27. 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

  28. 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

  29. DUPLEX
    2BR w/ Diamond Head Views & Lanai

    2BR w/ Diamond Head Views & Lanai

    Honolulu, HI

    Your Manoa Valley crew of five will adore this lovely 2BR duplex. Unique Craftsman touches include captivating stained glass windows, while an outdoor shower provides added convenience. Find another full living room on the enclosed lanai and views...

    Pets OK
    FREE CANCELLATION

    $236 to $685/night

  30. CONDOMINIUM
    Kona Bali Kai Studio w/ Pool & Spa

    Kona Bali Kai Studio w/ Pool & Spa

    Kailua Kona, HI

    As part of the exclusive Kona Bali Kai Resort, this updated studio features a private balcony. Take a dip in the sparkling shared pool or soak in the spa.A prime location just steps from the popular Banyan Surf Beach; spend sun-filled days...

    Pool Hot Tub
    FREE CANCELLATION

    $110 to $241/night