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
    Holua Kai #34

    Holua Kai #34

    Kailua Kona, HI

    Situated in the exclusive, gated oceanfront community of Holua Kai, this luxurious and inviting home provides the perfect setting for your Hawaiian getaway. The home comfortably accommodates six and is just a 10-minute walk from Keauhou Bay, the...

    Pool

    $423 to $839/night

  2. CONDOMINIUM
    Kaleialoha 205

    Kaleialoha 205

    Lahaina, HI

    A direct Beach/Oceanfront condo with an amazing view. Beach and ocean access for swimming, snorkeling, whale watching and relaxing in the sun. You can't get closer to the ocean than this unless you're on a boat. Watch the whales December through...

    Pool
    FREE CANCELLATION

    $186 to $331/night

  3. HOUSE
    Hilo Shangrila

    Hilo Shangrila

    Keaau, HI

    Let the oceanfront, gated retreat of Hilo Shangrila envelope you, with its private saltwater pool, hot tub, and covered lanai, all just a stone's throw from the peaceful Pacific. New air conditioning has been added in all bedrooms for total guest...

    Pool Hot Tub

    $417 to $1,054/night

  4. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    'Kona Bubbles' is a absolute spectacular property that Knutson & Associates is extremely proud to be newly representing as of November 2018. A gorgeous home in gated Meilani View Estates with ocean views just above Kailua Kona. Recently finished in...

    Pool
    FREE CANCELLATION

    $1,320 to $1,395/night

  5. CONDOMINIUM
    Ilikai 1820

    Ilikai 1820

    Waikiki, HI

    STUNNING OCEAN & SUNSET VIEWS! STEPS TO WAIKIKI BEACH. Memorable Meals from the Lanai. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life. Beautiful high end recent remodel. Fully equipped and...

    Pool
    FREE CANCELLATION

    $146 to $287/night

  6. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Island living at its finest! Experience charming plantation style living in this gorgeous Poipu home. Enjoy all the Robert Trent Jones, Jr. community has to offer conveniently located along the Kiahuna Golf Course. Shopping, golf, and beach...

    Pool Hot Tub

    $839 to $1,971/night

  7. HOUSE
    House of the Turtle at Champion Ridge, Mauna Lani (CR 18)

    House of the Turtle at Champion Ridge, Mauna Lani (CR 18...

    Kamuela, HI

    House of the Turtle - Limited Time Low Rates for August through October 31! $1049 per night! Tranquility and luxury await in this single-level residence with spectacular Kohala Mountain views in the desirable gated Champion Ridge community....

    Pool Hot Tub

    $1,373 to $4,078/night

  8. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Experience a vacation of a lifetime in this massive oceanfront custom home tucked away in an exclusive and quiet gated community along the Kona coast. A pond with a waterfall, filled with flowers welcomes you upon entering this beautiful custom...

    Pool Hot Tub

    $1,150 to $1,605/night

  9. HOUSE
    Kona Bay Bliss

    Kona Bay Bliss

    Kailua Kona, HI

    This incredible home is secluded in a 24 hour guard gated oceanfront community, yet is close to all that Kona has to offer. It is located just a short walk from the classic old Hawaiian town of Kailua and the start/finish of the Ironman. In all of...

    Pool Hot Tub

    $1,343 to $2,014/night

  10. HOUSE
    Honu O Kai (Turtle of the Sea)

    Honu O Kai (Turtle of the Sea)

    Kailua Kona, HI

    Welcome to Honu O Kai (Turtle of the Sea). Just two miles from the ocean, makes this spacious, four bedroom home one of the best places to stay on the Big Island. This two level home offers wide open spaces, two kitchens, both big enough for all...

    Pool

    $508 to $771/night

  11. CONDOMINIUM
    Ilikai 1122

    Ilikai 1122

    Waikiki, HI

    STUNNING OCEAN, LAGOON VIEWS! STEPS TO WAIKIKI BEACH. Memorable Meals and fireworks from the Lanai. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life. Beautiful high end recent remodel. Fully...

    Pool
    FREE CANCELLATION

    $141 to $262/night

  12. HOUSE
    Mauna Kea Fairways North #9

    Mauna Kea Fairways North #9

    Kamuela, HI

    The vacation of a lifetime awaits at Mauna Kea Fairways North, a gated community within the premier resort area of Hawaii Island. Mauna Kea Fairways North #9 boasts three en suite bedrooms, air conditioning, a private pool and spa, and views of the...

    Pool Hot Tub

    $1,791 to $3,695/night

  13. CONDOMINIUM
    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    Lahaina, HI

    The ultimate in luxury awaits at our completely remodeled and refurnished 1 bedroom, 1 bathroom oceanfront condo. Just steps from the water, this truly exceptional suite offers spectacular unobstructed ocean and sunset views from the lanai and...

    Pool
    FREE CANCELLATION

    $251 to $346/night

  14. CONDOMINIUM
    Kaleialoha 210

    Kaleialoha 210

    Lahaina, HI

    Imagine yourself staying at this incredible 1 bedroom Ocean Front Condo!! Views of the gorgeous Pacific Ocean and the neighboring islands from your lanai. Watch sea turtles eat seaweed off of the coral right below the lanai as well as watch...

    Pool
    FREE CANCELLATION

    $173 to $628/night

  15. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    IS 210-SUMMER Special Prices! Tranquil Oceanfront 1-Bedroom, 1-Bathroom Condo in Maalaea: Maui's Best Kept Secret! We invite you to be our guest in our 1-bedroom, 1-bath oceanfront home. There is an air conditioner in the living room to keep...

    Pool
    FREE CANCELLATION

    $163 to $366/night

  16. CONDOMINIUM
    Kihei Akahi C-616

    Kihei Akahi C-616

    Kihei, HI

    Imagine yourself sitting on the lanai with a drink in hand, watching the gorgeous colors of the Hawaiian sunset! This is a perfect budget getaway. Come explore the island! See gorgeous beaches, taste the island cuisine, shop the local businesses and...

    Pool
    FREE CANCELLATION

    $158 to $543/night

  17. CONDOMINIUM
    Island Surf 409

    Island Surf 409

    Kihei, HI

    This adorable new 1bd/1ba condo sits across from Kalama Park in the heart of beautiful Kihei. You'll get to enjoy stunning ocean and mountain views, AC, and all the comforts of home! If you're looking for a place to relax and enjoy Maui, look no...

    Pool
    FREE CANCELLATION

    $158 to $543/night

  18. CONDOMINIUM
    Kihei Alii Kai A207

    Kihei Alii Kai A207

    Kihei, HI

    Brand New Renovation! This spacious 1-bedroom, 1 bathroom condo is fully furnished and offers AC, wifi, cable, Dvd player, hairdryer, an in-unit washer and dryer, iron/ironing board, and so much more! You'll also get to enjoy the brand new sofabed...

    Pool Hot Tub
    FREE CANCELLATION

    $158 to $543/night

  19. CONDOMINIUM
    Kauhale Makai 203

    Kauhale Makai 203

    Kihei, HI

    Relax and enjoy Maui from this adorable 1bd/1ba condo! This unit offers all the comforts of home with WiFi, Cable, DVD Player, and Central AC. You'll also get to enjoy the fully-stocked kitchen, on-site laundry room, and private ocean-view and...

    Pool Hot Tub
    FREE CANCELLATION

    $130 to $548/night

  20. CONDOMINIUM
    Honua Kai Hokulani 316 1BR

    Honua Kai Hokulani 316 1BR

    Lahaina, HI

    Suite 316 is located on the 3rd floor in the south building, called HOKULANI. This 1 bedroom/1bath unit is spacious at 700 square feet, plus a 145 square feet lanai. The suite is south facing and enjoys both ocean and mountain views. Being a...

    Pool Hot Tub
    FREE CANCELLATION

    $328 to $474/night

  21. HOUSE
    Mahuahua Hale

    Mahuahua Hale

    Kailua Kona, HI

    This 2700+ square ft. house is perfect for entertaining family and friends! With so much space you can accommodate everyone's needs; whether that be barbecuing down by the pool with friends or finding a quiet, private spot to relax with a favorite...

    Pool
    FREE CANCELLATION

    $525 to $642/night

  22. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Welcome to Hale Lani! This gorgeous house is a BRAND NEW VACATION RENTAL that Knutson & Associates Management is proud to represent. Hale Lani is the perfect spot to host a unforgettable Hawaii Vacation. With 4 bedrooms, and a capacity to sleep 14,...

    Pool
    FREE CANCELLATION

    $1,173 to $1,535/night

  23. HOUSE
    Heeia Bay Hale

    Heeia Bay Hale

    Kailua Kona, HI

    Welcome to the listing page of Heeia Bay Hale! A Brand New Vacation Rental as of October 2018. This wonderful 2 story home in Keauhou is WALKING DISTANCE TO HEEIA BAY!! This private & spacious 3 bedroom, 3.25 bath multi-level Hawaiian style beach...

    Pool
    FREE CANCELLATION

    $467 to $774/night

  24. HOUSE
    Blue Hawaii

    Blue Hawaii

    Kailua Kona, HI

    Blue Hawaii a 3200 square ft. property provides a great experience for family and friends. This large well-appointed home is perfect for a large group. Because of the size of this property, you have the space to entertain both inside and out. The...

    Pool

    $744 to $2,322/night

  25. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Mauna Kea condo description Rare 3BR * Sleeps 6 * Panoramic Ocean Views * On 4th Fairway * Amenity Cards Available with fee*  Kumulani G-1, our 3-bedroom, 2-bathroom condominium home in the world-famous Mauna Kea Resort, has an Ocean view and...

    Pool Hot Tub

    $342 to $646/night

  26. HOUSE
    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    Princeville, HI

    This custom designed home by Hawaii's renowned architect Mark Eyler is located on the idyllic northshore of Kauai. Designed for professional surfer Bruce Irons, the architecture and interior design blends Balinese, Hawaiian and Asian elements with a...

    Pool

    $1,553 to $3,338/night

  27. ESTATE
    Hale Kauka

    Hale Kauka

    Kamuela, HI

    ***This property is currently for sale and may be shown during your stay. The property manager will contact you to make arrangements for showings.*** ***Please note there is a 7 night minimum during the holidays. Christmas reservations must check...

    Pool

    $958 to $1,375/night

  28. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    This stunning Poipu home boasts over 3,300 square feet of elegant living space, along with sweeping views from the coastline up the sloping hills of Kalaheo. An open floor plan provides guests with the perfect setting for quality time together,...

    Pool Hot Tub

    $899 to $2,124/night

  29. 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

  30. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Hale Pua (“House of Flowers”) is one of the few 5 bedroom/6 full bath oceanfront vacation rental homes with its own private pool & spa in the Kailua-Kona area. For recent candid photos and input from guests, please visit our FB page,...

    Pool Hot Tub

    $1,938 to $2,627/night