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
    Wailea Elua Unit #0902

    Wailea Elua Unit #0902

    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

    $482 to $1,065/night

  2. 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

  3. 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

  4. CONDOMINIUM
    Maui Kaanapali Villas #A101

    Maui Kaanapali Villas #A101

    Lahaina, 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

  5. 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

    $481 to $1,171/night

  6. 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

    $481 to $896/night

  7. CONDOMINIUM
    Hale Kai O'Kona

    Hale Kai O'Kona

    Kailua Kona, HI

    Hale Kai O'Kona is an exclusive oceanfront Hawaii vacation home one mile south of the town of Kailua-Kona, on the Big Island of Hawaii. Our home is a 2400 Sq. Ft. end property with no connecting walls. The beauty and privacy of this 4 bedroom, 3...

    Pool

    $479 to $642/night

  8. HOUSE
    826 Kaahue Street Home

    826 Kaahue Street Home

    Honolulu, HI

    Prepare to be wowed by unforgettable views at this 4BR/3BA home, ideally situated in Honolulu’s beautiful Hawaii Kai. Overlooking Maunalua Bay, Koko Marina, and Hawaii Kai, you’ll enjoy sweeping ocean and Koko Head vistas from almost every room...

    FREE CANCELLATION

    $478 to $890/night

  9. CONDOMINIUM
    Menehune Shores Unit #218

    Menehune Shores Unit #218

    Maui, HI

    A note from the owner: Unit 218 has been completely remodeled in 2006. It is a spacious 3 bedroom condo and is great for larger families or couples traveling together. This ocean front condo has spectacular outer island views. The condo is well...

    Pool

    $477 to $533/night

  10. CONDOMINIUM
    Menehune Shores Unit #515

    Menehune Shores Unit #515

    Maui, HI

    This center unit, ideally situated, offers unsurpassed, panoramic views of the ocean and neighboring islands. Step onto the lanai, experience the soft sea breeze and rejoice in your arrival! Sit, relax, and watch paddlers in outriggers glide across...

    Pool

    $477 to $533/night

  11. TOWNHOUSE
    Pili Mai 11I

    Pili Mai 11I

    Koloa, HI

    Enjoy modern Hawaii living at Pili Mai 11I Pack your golf clubs and get ready to enjoy modern Hawaii living in this exclusive Poipu community. Located on the 9th hole of the beautiful Kiahuna Golf Course, this exceptionally beautiful,...

    Pool Hot Tub

    $476 to $1,137/night

  12. CONDOMINIUM
    Honua Kai Konea 705

    Honua Kai Konea 705

    Kaanapali, HI

    WOW! HUGE OCEAN VIEWS WITH SUNSETS ALL YEAR LONG!!! This spectacular 7th Floor OCEAN VIEW 2 bed2 bath home is one of the finest at the Honua Kai Resort & Spa. JUST UPGRADED WITH NEW DESIGNER FURNISHINGS AND PORCELAIN TILE FLOORING THROUGHOUT! The...

    Pool Hot Tub

    $473 to $1,706/night

  13. 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

  14. CONDOMINIUM
    Oceanfront 3BR w/ Private Beach & AC

    Oceanfront 3BR w/ Private Beach & AC

    Kihei, HI

    Feel Pacific breezes as you unwind on the lanai of your fourth-floor 3BR/2BA condo. This unit commands the most sought-after location in the building (front and center), closest to the ocean and furthest from the road. Take in stunning wide-open...

    Pool
    FREE CANCELLATION

    $471 to $794/night

  15. CONDOMINIUM
    WAILEA ELUA, #1601*

    WAILEA ELUA, #1601*

    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

    $471 to $896/night

  16. CONDOMINIUM
    Grand Champions #089

    Grand Champions #089

    Wailea, HI

    Remodeled two bedroom condo at Wailea Grand Champions with fabulous views of the golf course. This condo completed renovations in November 2016 and features a completely renovated Kitchen and bathrooms and new furnishings. The Kitchen has new...

    Pool Hot Tub
    FREE CANCELLATION

    $469 to $688/night

  17. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-104

    Keauhou Kona Surf & Racquet Club #5-104

    Kailua Kona, HI

    Welcome to unit #5-104 at the Keauhou Kona Surf & Racquet Club. Knutson & Associates Property Management is so proud to be newly representing this absolutely breathtaking corner unit. #5-104 is a immaculate, remodeled ground floor unit in the best...

    Pool
    FREE CANCELLATION
  18. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-303

    Keauhou Kona Surf & Racquet Club #5-303

    Kailua Kona, HI

    **Brand New Property In Our Inventory.* 5-303 at the Surf & Racquet Club is a jaw dropping, absolutely gorgeous top floor condo located in the best building in the complex. Building 5. The most Private of them all. Come stay at this beautifully...

    Pool
    FREE CANCELLATION
  19. CONDOMINIUM
    Casa De Emdeko 219

    Casa De Emdeko 219

    Kailua Kona, HI

    **Newly Remodeled Kitchen And Master Bathroom As Of September 2018.** Casa#219 is a direct oceanfront 2 bedroom. 2 bath property that sits right on the water. Huge lanai. This unit has everything you will need to feel like you are royalty a great...

    Pool
    FREE CANCELLATION
  20. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Kona Makai 3-302 is a gorgeous top floor, spacious condo that's been recently updated! Great showmanship of pride in property. Nice ocean view. Loft! Essentially a 2 bedroom for the price of 1! The Kona Makai is a beautiful sunny highly sought after...

    Pool Hot Tub
    FREE CANCELLATION

    $466 to $485/night

  21. CONDOMINIUM
    Wailea Elua #207

    Wailea Elua #207

    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

    $464 to $725/night

  22. CONDOMINIUM
    Wailea Elua #102

    Wailea Elua #102

    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 Hot Tub
    FREE CANCELLATION

    $464 to $696/night

  23. HOUSE
    Iki Nui Hale

    Iki Nui Hale

    Princeville, HI

    This home is a short walking distance to Queen's Bath as well as Hideaways Beach! For all you golf enthusiasts, Makai Golf Course is a short walk from this home as well! The Princeville Public Library, Princeville Park as well as the shopping center...

    $464 to $933/night

  24. VILLA
    Luxury 3bed/3bath Hideaway

    Luxury 3bed/3bath Hideaway

    Kihei, HI

    Lele Hideaway is a three bedroom, 3 bath two-level condominium suite. Two bedrooms each have a full bathroom and are located on the ground floor. The third bedroom is located below ground level, down a spiral staircase from the living room. The...

    Pool Hot Tub

    $463 to $52,200/night

  25. VILLA
    Poolside Bungalow 3bed/3bath, w/ Pool & Hot Tub- Steps To Beach

    Poolside Bungalow 3bed/3bath, w/ Pool & Hot Tub- Ste...

    Kihei, HI

    Poolside Bungalow is a three bedroom, 3 bath two-level condominium suite. Two bedrooms each have a full bathroom and are located on the ground floor. The third bedroom is located below ground level, down a spiral staircase from the living room. The...

    Pool

    $463 to $984/night

  26. CONDOMINIUM
    Wailea Elua Unit #0307

    Wailea Elua Unit #0307

    Wailea, HI

    A note from the owner: Welcome to Wailea Elua Village #307, our newly remodeled ground floor condo and our piece of paradise. With outstanding views, beach access through beautifully sculpted gardens, and Hawaiian-home class, it has everything you...

    Pool Hot Tub

    $459 to $953/night

  27. CONDOMINIUM
    Wailea Elua Unit #1503

    Wailea Elua Unit #1503

    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

    $459 to $953/night

  28. HOUSE
    Waterfall House

    Waterfall House

    Kailua-Kona, HI

    Beautiful high end home with views directly to the ocean below. Have your own private retreat within a secure, gated community in an expansive open home. Stay in perhaps one of the most unique homes in Hawaii where it rains into the house, filling...

    Pool Hot Tub

    $459 to $1,721/night

  29. CONDOMINIUM
    Wailea Elua Unit #0802

    Wailea Elua Unit #0802

    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 Hot Tub

    $459 to $953/night

  30. CONDOMINIUM
    Wailea Elua Unit #801

    Wailea Elua Unit #801

    Wailea, HI

    Notes from the Owner: Wailea Elua Village #801 is located in the center of the Elua Village just across from the small pool and Jacuzzi area and just steps to the paddle court. Enjoy ocean views as well as secluded garden views from this quiet...

    Pool Hot Tub

    $459 to $953/night