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
    Papakea E306

    Papakea E306

    Lahaina, HI

    One of the nicest ocean view units in Papakea. Highly upgraded with all the amenities you expect. Living room Air Conditioning, designer granite, Bosch dishwasher, GE washer/dryer, flat surface range/oven, LCD flat screen TV's in both living room...

    Pool Hot Tub

    $203 to $314/night

  3. CONDOMINIUM
    Kona Bali Kai 223- Oceanfront

    Kona Bali Kai 223- Oceanfront

    Kailua Kona, HI

    Lovely Oceanfront upgraded second floor 2bd2bth unit in Kona Bali Kai one of Kona's most popular oceanfront destinations. Watch the surfers at "Banyans" from your lanai at one of Kona's premier surfing spots. Light, Bright, and Airy with several...

    Pool
    FREE CANCELLATION

    $181 to $242/night

  4. 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

  5. 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

  6. 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

  7. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    An incredibly comfortable unit! This renovated one bedroom unit fronts directly on a beautiful white sand beach. You'll have just enough lawn area to stretch out and shake the sand off before stepping directly into your beautiful ocean side living...

    FREE CANCELLATION

    $195 to $324/night

  8. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Welcome to Wai'ula'ula at the Mauna Kea Resort! Your vacation will truly be one to remember in this beautifully decorated condominium in the gated community of Wai'ula'ula is located on the Hapuna Golf Course. This recently built luxury development...

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  9. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Book a memorable Maui vacation at this third-floor 1BR condo in central Kihei. With open-concept living and an additional sleeper sofa, there’s plenty of room for four people. Step out to your private lanai with retractable net enclosure and take...

    Pool
    FREE CANCELLATION

    $131 to $326/night

  10. 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

  11. CONDOMINIUM
    Kanaloa 202

    Kanaloa 202

    Keauhou, HI

    Historic and Charming Keauhou Bay is just steps away from Kanaloa at Kona. The premier resort in Keauhou Resort area. The location is perfect. Close to supermarket, restaurants, shopping, golf, beaches, sport fishing, and other vacation activities....

    Pool
    FREE CANCELLATION

    $169 to $230/night

  12. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 215 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

    $275 to $413/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
    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua, HI

    Over $600K in recent upgrades! Even the best photos can not capture the true beauty of the high-end materials used, the designer furniture and accessories and the magnificent views that surround this 5 star property.Wrap yourself in the luxury of...

    Pool

    $563 to $1,063/night

  15. CONDOMINIUM
    Kaleialoha #115

    Kaleialoha #115

    Lahaina, HI

    Lovely corner unit with all one side louvered windows to let the outside in!Recently upgraded with gorgeous granite counter, all new appliances and tile through out! Unit has unique four poster bed, walk in tiled shower, AC in living area, in suite...

    Pool
    FREE CANCELLATION

    $207 to $384/night

  16. 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

    $144 to $231/night

  17. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    This brand new upscale luxury condo is located in the privately gated new Waikoloa Beach Villas Complex, close to the activity center with two pools, fitness workout room and spa areas. Unit includes discounted GOLD GOLF KINGS' CLUB MEMBERSHIP....

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  18. 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

    $224 to $464/night

  19. CONDOMINIUM
    Kuleana 706 1 Bdrm

    Kuleana 706 1 Bdrm

    Lahaina, HI

    Enjoy the luxury of this beautiful oceanfront condo including all brand new furniture! You will find travertine floors, granite counter tops in the kitchen, an island bar, and bathroom with a custom walk in shower. There is a heavenly King Bed in...

    Pool
    FREE CANCELLATION

    $269 to $461/night

  20. HOUSE
    Holoholo ku Waimea

    Holoholo ku Waimea

    Waimea, HI

    HoloHolo Ku is the most charming neighborhood. It's like living in a storybook with huge ranch lands, horses and the view of beautiful Mauna Kea. Walk to town and walk to one of the most famous farmer's markets in Waimea. Minimum 30 Day Rental The...

    FREE CANCELLATION

    $193 to $255/night

  21. HOUSE
    Hale Kohola

    Hale Kohola

    Hilo, HI

    Hale Kohola “The House of the Whale” is situated on 3 acres in an ideal location on the Kohala Coast, with panoramic views of the ocean and coastline. The master bedroom has a stunning ocean view that you can enjoy by just lifting your head off...

    FREE CANCELLATION

    $347 to $466/night

  22. CONDOMINIUM
    Ocean and Pool View Beachfront 2nd Floor Villa 208

    Ocean and Pool View Beachfront 2nd Floor Villa 208

    Kahuku, HI

    This villa is located on the second level with Spectacular Ocean and pool views from the lanai, the living room, the dining room, and the master bedroom! This villa is just 35 yards from the sandy beach and 10 yards to the Pool and BBQs. It has...

    Pool Hot Tub

    $912 to $2,147/night

  23. TOWNHOUSE
    Na Hale o Keauhou H3

    Na Hale o Keauhou H3

    Kailua-Kona, HI

    Na Hale O Keauhou is a newer complex of townhomes located just 6 miles South of Kona.Our unit is at the quiet Northern end of the complex that overlooks a protected preservation areawith unencumbered panoramic white water ocean views and beyond. No...

    Pool Hot Tub
    FREE CANCELLATION

    $237 to $359/night

  24. CONDOMINIUM
    Valley Isle #1104

    Valley Isle #1104

    Lahaina, HI

    Perched on the 11th floor of the beautiful, lush, ocean-front Valley Isle Resort, this 1-Bedroom/1-Bath condo boasts panoramic views of the ocean and the islands of Molokai'i and Lana'i. The best sunsets you can imagine. Whale-watching at its best....

    Pool
    FREE CANCELLATION

    $173 to $291/night

  25. CONDOMINIUM
    Wailea Elua #701

    Wailea Elua #701

    Wailea, HI

    The Wailea Elua is the premier ocean front property in Wailea. Situated right on Ulua Beach, it has one of the best locations in Wailea. There are miles of spectacular walking paths that follow the ocean In addition the property has two swimming...

    Pool Hot Tub
    FREE CANCELLATION

    $493 to $922/night

  26. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Oceanfront estate with breathtaking panoramic unobstructed views. 4 BR, 4 elegant baths. All bedrooms have oceanfront balconies. Walls of glass open to lanai & main living area making this an ideal Hawaiian indoor/outdoor living experience. Elegant...

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  27. CONDOMINIUM
    Casa De Emdeko 330

    Casa De Emdeko 330

    Kailua Kona, HI

    ***COMPLETE REMODEL COMPLETED JANUARY 2016 IN CONDO! Owners have extensively updated the condo from top to bottom.Flooring, Bathroom, Kitchen, Furniture, Lanai all updated! Be one of the first guests to enjoy this renovation!TAKE A VIRTUAL TOUR OF...

    Pool
    FREE CANCELLATION

    $239/night

  28. CONDOMINIUM
    Papakea G206

    Papakea G206

    Lahaina, HI

    Brand new washer and dryer. Brand new refrigerator. Brand new living room carpet. New curtains in both rooms and living room.Enjoy the ocean view from this cozy condo. It has a remodeled kitchen with granite counter tops. Fully stocked with...

    Pool Hot Tub

    $232 to $387/night

  29. 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

  30. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Sprawling, Exclusive Hali’i Kai Condo 22FImagine this: You wake up to balmy Hawaiian breeze and wander onto your bedrooms personal lanai to watch the morning sun on the mountains. After a hike along the lava-rock seashore, you take a dip in the...

    Pool Hot Tub

    $330 to $689/night