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 501

    Mahana 501

    LAHAINA, HI

    This brand-new beautiful new 5th floor listing at the Mahana at Kaanapali boasts gorgeous views of both the tranquil blue Pacific Ocean AND the lush West Maui Mountains. This property is extremely close to the water, you can literally sit in the 5th...

    Pool Hot Tub
    FREE CANCELLATION

    $499 to $1,764/night

  2. CONDOMINIUM
    Mahana 701

    Mahana 701

    Lahaina, HI

    Beautiful 7th floor 2br/2ba 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
    FREE CANCELLATION

    $499 to $1,665/night

  3. CONDOMINIUM
    Honua Kai Hokulani 509

    Honua Kai Hokulani 509

    Kaanapali, HI

    Hokulani #509 is located in one of the most desirable stacks on the entire property. Forward facing interior corner view location for catching the whales or just watching the SUNSET. This fabulous 2 bedroom/2 bath upgraded condo is in the Hokulani...

    Pool Hot Tub

    $495 to $1,790/night

  4. CONDOMINIUM
    Wailea Elua Unit #0202

    Wailea Elua Unit #0202

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $494 to $1,065/night

  5. VILLA
    Ridge 1214 Gold Ocean View

    Ridge 1214 Gold Ocean View

    Kapalua, HI

    This luxurious retreat will spoil you forever. You’ll feel like you’re on top of the world as you take in spectacular views of the Pacific Ocean and the lush green landscape that surrounds you. You’ll feel your last care melt away as the warm...

    Pool

    $494 to $856/night

  6. VILLA
    Ridge1112 Ocean View

    Ridge1112 Ocean View

    Kapalua, HI

    Enjoy 5 star accommodations in an exclusive private villa paradise! Custom Designed and Fully Upgraded Ridge Villa with Ocean Views from Every Room! Designed from the onset to take advantage of its unique Island setting, Kapalua Ridge Villa 1112 is...

    Pool

    $494 to $869/night

  7. CONDOMINIUM
    Wailea Elua #701

    Wailea Elua #701

    Kihei, 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
    FREE CANCELLATION

    $493 to $922/night

  8. TOWNHOUSE
    Keauhou Kona Surf & Racket Club Townhouse #4

    Keauhou Kona Surf & Racket Club Townhouse #4

    Kailua Kona, HI

    ***Brand New Property In Vacation Rental Inventory*** 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...

    Pool
    FREE CANCELLATION
  9. CONDOMINIUM
    Kaanapali Shores #255

    Kaanapali Shores #255

    Lahaina, HI

    This Hawaiian themed condo has ocean views from the lanai and both bedrooms in Ka'anapali. Remodeled and updated. The guest bathroom has a glass block walk-in shower only-no tub. Bring your DVD's from home and watch them on the flat screen TV in the...

    Pool
    FREE CANCELLATION

    $493 to $800/night

  10. HOUSE
    Ainamalu Home 69-9242

    Ainamalu Home 69-9242

    Waikoloa Village, HI

    Come and enjoy a luxurious laid-back island living in our new home located in the beautiful new neighborhood in Waikoloa Beach Resort – Ainamalu. This gated community Ainamalu is the newest resort community in the beautiful Waikoloa Beach Resort,...

    FREE CANCELLATION

    $493 to $896/night

  11. DUPLEX
    Terrace Duplex Unit #A

    Terrace Duplex Unit #A

    Honolulu, HI

    All photos, amenities, calendar, and rates are 100% accurate. We will notify you proactively when early check-in / late check-outs are possible and you'll receive the comforts of home with a starter supply of shampoo, soaps, paper products and...

    Hot Tub Pets OK
    FREE CANCELLATION

    $493 to $744/night

  12. CONDOMINIUM
    Kapalua Golf Villas 12T5

    Kapalua Golf Villas 12T5

    Kapalua, HI

    Relax and enjoy the tranquil setting of this luxurious Kapalua Golf Villa. Let the gorgeous greenery captivate and soothe your soul. This unit has been remodeled with only top of the line materials and furnishings and is well apointed. Spend your...

    Pool
    FREE CANCELLATION

    $493 to $626/night

  13. CONDOMINIUM
    Papakea L405

    Papakea L405

    Lahaina, HI

    You will not find a nicer penthouse oceanfront unit at the Papakea Resort. From your lanai and the master bedroom, you can watch the whales play in the ocean seasonally and see the honu (turtles) swim all year round. This unit has an oceanfront...

    Pool Hot Tub

    $491 to $737/night

  14. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    One of the nicest penthouse units at Papakea Resort. From your lanai and the master bedroom, watch the whales play and the honu (turtles) swim. The KING bed in master bedroom allows you to sleep to the sounds of the ocean just 25 feet away. The...

    Pool Hot Tub

    $491 to $707/night

  15. CONDOMINIUM
    Hanalei Colony Resort I1

    Hanalei Colony Resort I1

    Hanalei, HI

    Hanalei Colony Resort I1 is unique among north shore Kauai condo complexes. It's directly on the path to follow, just take a few steps and you're on the sand. You can also take advantage of the restaurant and spa onsite, or prepare your own food in...

    Pool
    FREE CANCELLATION

    $488 to $581/night

  16. HOUSE
    1332 Mokolea Dr Home

    1332 Mokolea Dr Home

    Kailua, HI

    Located in the upscale neighborhood of Lanikai, this 3BR/2BA ocean tree house is strolling distance to Lanikai Beach — regarded as one of the world's most beautiful top beaches, with its flour-soft white sands, cooling ocean breezes, and pristine...

    FREE CANCELLATION

    $488 to $803/night

  17. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Hanalei Colony Resort E3 is unique among north shore Kauai condo complexes. It's directly on the path to follow, just take a few steps and you're on the sand. You can also take advantage of the restaurant and spa onsite, or prepare your own food on...

    Pool
    FREE CANCELLATION

    $488 to $581/night

  18. CONDOMINIUM
    Sands of Kahana #292

    Sands of Kahana #292

    Kahana, HI

    9th Floor Ocean Front 3 bedroom, 3 bath Penthouse at the beautiful Sands of Kahana with exquisite views of the neighboring islands. This spacious 3 bedroom condo allows for plenty of room and seating areas for the entire family. A fully equipped...

    Pool
    FREE CANCELLATION

    $487 to $1,183/night

  19. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Beautifully appointed "like new" 2 bedroom 2.5 bath oceanfront home with pool. Gourmet kitchen and huge deck for tanning, dining & sunset cocktails. Upstairs master has shower & hot tub. Sliding doors disappear into walls for the ultimate "on the...

    Pool

    $486 to $608/night

  20. CONDOMINIUM
    O-226: Hale Ka Wailele Malu Ko Olina Beach Villa

    O-226: Hale Ka Wailele Malu Ko Olina Beach Villa

    Kapolei, HI

    Hale Ka Wailele Malu is one of the most unique and desirable Beach Villas in all of Ko'Olina. The large (1,650 sq ft) 3 bedroom, 3 bathroom, 2nd floor, ocean-facing Beach Villa is one of only four Villas (out of the 247) that fronts the soothing and...

    Pool Hot Tub

    $485 to $1,668/night

  21. CONDOMINIUM
    O-1406: Hale Ikena Ko Olina Beach Villa

    O-1406: Hale Ikena Ko Olina Beach Villa

    Kapolei, HI

    Leave the world behind as you’re greeted by the warm blue expansive ocean views from the living area and spacious lanai (balcony) of Hale Ikena Ko Olina Beach Villa. This incredible 2 bedroom, 2 bathroom Penthouse condo in the Ocean Tower has...

    Pool Hot Tub

    $485 to $1,384/night

  22. CONDOMINIUM
    B-903 Beach Villa

    B-903 Beach Villa

    Kapolei, HI

    Beachfront Living at its finest! This 3 bedroom, 3 bath Villa is located in the beautiful Ko Olina Resort on the quiet West side of Oahu. The Beach Villas are the newest, and only, beachfront condominiums available on the island in 25 years....

    Pool

    $485 to $1,784/night

  23. CONDOMINIUM
    B-904: Hale Kai Ko Olina Beach Villa

    B-904: Hale Kai Ko Olina Beach Villa

    Kapolei, HI

    Beachfront Living at its finest! This 3 bedroom, 3 bath Villa is located in the beautiful Ko Olina Resort on the quiet West side of Oahu. The Beach Villas are the newest, and only, beachfront condominiums available on the island in 25 years....

    Pool Hot Tub

    $485 to $1,784/night

  24. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    Experience beach living in this beautiful vacation home on Puako Beach. This private residence is located right across the street from the ocean. Great place to kayak and snorkel in one of the best snorkeling spots on the Big Island. Or bask with...

    FREE CANCELLATION

    $485 to $652/night

  25. HOUSE
    Keauhou Estates #185

    Keauhou Estates #185

    Kailua Kona, HI

    Experience privacy and panoramic Pacific views just ten minutes from endless dining and shopping options in downtown Kailua-Kona. Situated in the exclusive gated Keauhou Estates community, this elegant custom home features three bedrooms and two...

    Hot Tub

    $482 to $780/night

  26. HOUSE
    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    Kailua Kona, HI

    ***Please note there is a 7 night minimum during the holidays. Christmas reservations must check out by 10AM on Dec. 27 and New Year's reservations can check in on Dec. 27 or after for a week. There is a 14 night minimum to book both Christmas and...

    Pool

    $482 to $720/night

  27. HOUSE
    Kahakai Estates Hale

    Kahakai Estates Hale

    Kailua Kona, HI

    This charming home is ideally situated in the gated community of Kahakai Estates on the Big Island's spectacular Kona Gold Coast. Experience the seclusion of your own Hawaiian hideaway just two miles southwest of all the incredible attractions and...

    Pool Hot Tub

    $482 to $839/night

  28. COTTAGE
    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    Kamuela, HI

    This spectacular 3 bedroom- 3 bath single-level cottage is located within Kamilo, which is nestled near the heart of the Mauna Lani Resort area. Upon entering Mauna Lani KaMilo Home (424) enjoy the vaulted ceilings and open floor plan which allows...

    Pool Hot Tub

    $482 to $1,197/night

  29. CONDOMINIUM
    Maui Kaanapali Villas #A101

    Maui Kaanapali Villas #A101

    Kaanapali, HI

    Luxury + Privacy = Our Maui Kaanapali Villa Vacation Rental Home. Our Villa, located on the ocean side ground level of Aloha Tower, represents the finest in gracious Hawaiian living. Featuring soaring ceilings and fine Asian art throughout, this 2...

    Pool
    FREE CANCELLATION

    $481 to $1,167/night

  30. CONDOMINIUM
    Wai'ula'ula D201 Condominium

    Wai'ula'ula D201 Condominium

    Waimea, 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, located on the Hapuna Golf Course. This recently built luxury development...

    Pool
    FREE CANCELLATION

    $481 to $1,174/night