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
    Villas on the Prince 28

    Villas on the Prince 28

    Princeville, HI

    Villas on the Prince 28: NOTE: 30-DAY MINIMUM STAY AT THIS LOCATION. Enjoy this elegant, very private end unit which provides both mountain and golf course views. Inside you'll find three bedrooms and three bathrooms, as well as numberous...

    Pool
    FREE CANCELLATION

    $164 to $183/night

  2. CONDOMINIUM
    Waikiki Dream Vacation

    Waikiki Dream Vacation

    Honolulu, HI

    Beautifully remodeled 2 bedroom 2 bath with large lanai facing Diamond Head with Ocean and Mountain Views. free assigned, covered and secure parking. One queen bed in master bedroom. 2 twins in the view suite can be put together. Located centrally...

    Pool Hot Tub

    $292 to $352/night

  3. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This Villa is the owner’s primary residence under section 121 of IRC. The owners offer it for rent during limited periods. As such, it is Exempt from STVR rules, so it has no STVR registration #. TAT is TA-185-465-4464-01 . Villa operates in...

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $760/night

  4. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    One of West Maui's most exclusive legally permitted rental properties, the Makena Aloha Estate offers exceptional ocean and mountain views, with gated exclusive privacy and seclusion. With 4,400 square feet of interior dwelling space, this...

    Pool Hot Tub

    $1,538 to $3,075/night

  5. CONDOMINIUM
    Wailea Grand Champion, #154

    Wailea Grand Champion, #154

    Wailea, HI

    A note from the owner: This rare 3 bedroom ocean view, golf course view condo has been completely remodeled in 2011. It the absolute best location in the Grand Champions Villas boasting granite countertops and stainless steel appliances. Relax on...

    Pool

    $297 to $672/night

  6. CONDOMINIUM
    Papakea J103

    Papakea J103

    Lahaina, HI

    Quiet Garden Unit! Awesome Garden and Pond View! West Maui Kaanapali Papakea 2 bedroom, 2 bathroom, sleeps 6, ground floor condo 100 yards from the ocean's edge. Enjoy dinner or a cocktail with the awesome pond and garden view. Updated kitchen and...

    Pool Hot Tub

    $215 to $351/night

  7. CONDOMINIUM
    Papakea A309

    Papakea A309

    Lahaina, HI

    Direct Ocean Front! Sleep to the sound of the waves! West Maui Kaanapali Papakea 1 bedroom, 1 bathroom, sleeps 4, third floor corner condo 25 feet from the ocean's edge. Watch the whales, sunsets, and the ocean from the kitchen, living room and...

    Pool Hot Tub

    $234 to $357/night

  8. CONDOMINIUM
    Wailea Elua Unit #0302

    Wailea Elua Unit #0302

    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

    $448 to $823/night

  9. CONDOMINIUM
    Puu Poa 405

    Puu Poa 405

    Princeville, HI

    This spacious top floor condo in the upscale Puu Poa complex on the north shore of beautiful Kauai is located directly next door to the Princeville St Regis Hotel. You'll love the newly renovated oceanfront pool! Also available onsite are tennis...

    Pool
    FREE CANCELLATION

    $397 to $458/night

  10. CONDOMINIUM
    Plantation at Princeville 1322

    Plantation at Princeville 1322

    Princeville, HI

    Plantation at Princeville 1322: This elegant air-conditioned Kauai vacation rental at The Plantation at Princeville is close to everything! You'll be just a few minutes drive from great beaches like Anini, Hideaways, and Hanalei. It's one mile to...

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $306/night

  11. CONDOMINIUM
    Wailea Elua #2204

    Wailea Elua #2204

    Wailea, Maui, HI

    You will immediately sense that the fabulous Maui vacation you have been looking forward to has begun when you step into this completely remodeled 2 bedroom, 2 bath condo located on one of the best locations in the Wailea Elua Village. From our...

    Pool

    $650 to $1,065/night

  12. CONDOMINIUM
    Mahana Resort #1107

    Mahana Resort #1107

    Lahaina, HI

    Welcome to Mahana 1107! Located on the eleventh-floor, this recently remodeled one bedroom, one bath condo sleeps 2-4 and features stunning panoramic views of the ocean, beach and outer islands from the living room, dining area, bedroom, and lanai....

    Pool
    FREE CANCELLATION

    $325 to $638/night

  13. CONDOMINIUM
    Papakea #E207

    Papakea #E207

    Lahaina, HI

    This 1 bedroom, 1 bath remodeled ocean view condo at the beautiful Papakea Beach Resort in North Kaanapali in located in building E, on the North side of the complex. The second floor location is great for privacy as well as spectacular views of the...

    Pool
    FREE CANCELLATION

    $273 to $447/night

  14. CONDOMINIUM
    Hale Mahina #A207

    Hale Mahina #A207

    Lahaina, HI

    This Ocean Front unit is located right on a beautiful sandy beach in Honokowai, just north of Kaanapali. This Corner, Ocean Front, 1 bedroom condo houses spectacular views from the bedroom, living room, AND the kitchen. Listen to the Masters of the...

    Pool
    FREE CANCELLATION

    $191 to $414/night

  15. CONDOMINIUM
    Lahaina Shores #317

    Lahaina Shores #317

    Lahaina, HI

    New to program: Direct ocean front view from our 3rd floor remodeled condo located at the beautiful beach Resort in Lahaina Town: Lahaina Shores. Completely remodeled kitchen with granite counters and stainless steel appliances. Tile floors...

    Pool
    FREE CANCELLATION

    $226 to $435/night

  16. CONDOMINIUM
    Kaanapali Royal #M302

    Kaanapali Royal #M302

    Lahaina, HI

    This well-equipped, sleekly decorated Hawaiian style unit is remodeled with ocean and golf course views on the Kaanapali golf course. The master bedroom and bathroom are upstairs with ocean views as well. Enjoy a nice soak in the bathtub to unwind...

    Pool
    FREE CANCELLATION

    $278 to $1,032/night

  17. CONDOMINIUM
    Mahana Resort #813

    Mahana Resort #813

    Lahaina, HI

    Welcome to Mahana 813! Located on the eighth-floor, this oceanfront studio sleeps 2 and features stunning panoramic views of the ocean, beach and outer islands. Living area highlights include tile floor, 48" Smart HD TV (access your Netflix and Hulu...

    Pool
    FREE CANCELLATION

    $273 to $493/night

  18. 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

    $406 to $800/night

  19. CONDOMINIUM
    Mahana Resort #518

    Mahana Resort #518

    Lahaina, HI

    Ocean front on North Ka'anapali beach. An ocean front bedroom allows for a greater view from this 5th floor Mahana condo. Tastefully furnished in a tropical green theme with all the amenities. The bedroom has a new 40 inch LED flat screen TV with...

    Pool
    FREE CANCELLATION

    $232 to $574/night

  20. CONDOMINIUM
    Lahaina Shores #533

    Lahaina Shores #533

    Lahaina, HI

    SPECTACULAR OCEANFRONT LOCATION! Just steps from the ocean. See breaching whales and breathtaking sunsets from your private lanai (patio). Watch the cruise ships offshore and the surfers on the waves near the harbor. Fall asleep to the sounds of the...

    Pool
    FREE CANCELLATION

    $238 to $447/night

  21. CONDOMINIUM
    Kaanapali Shores #160

    Kaanapali Shores #160

    Lahaina, HI

    Settle into your Hawaiian vacation in this ocean front and ground floor condo with beach and pool access in Ka'anapali. Wake up to the smell of the ocean, just steps away from one of the most popular beaches in Maui. Kaanapali Shores #160 May...

    Pool
    FREE CANCELLATION

    $429 to $800/night

  22. CONDOMINIUM
    Papakea #L207

    Papakea #L207

    Lahaina, HI

    2nd floor 1 bedroom, 1 bath vacation condo with direct ocean front views in North Ka'anapali. This super adorable condo features a new king bed in the bedroom and there is a brand new queen sofa sleeper in the living room to sleep up to 4 guests...

    Pool
    FREE CANCELLATION

    $244 to $447/night

  23. CONDOMINIUM
    Papakea #G103

    Papakea #G103

    Lahaina, HI

    Remodeled with a partial ocean view our 2 bedroom is located on the ground floor in North Ka'anapali with easy access to pools and beach. Under new ownership as of March 2016 and owner has already completed the following updates: New microwave and...

    Pool
    FREE CANCELLATION

    $267 to $600/night

  24. CONDOMINIUM
    Mahana Resort #1003

    Mahana Resort #1003

    Lahaina, HI

    Welcome to Mahana #1003. We have named our special get-away “Nani”, which means beauty in Hawaiian, for the spectacular expanse of ocean and sky that one can see from our 10th floor ocean-front vacation home. The beautiful view will greet you...

    Pool
    FREE CANCELLATION

    $232 to $493/night

  25. CONDOMINIUM
    Lahaina Shores #505

    Lahaina Shores #505

    Lahaina, HI

    Magnificent ocean front views of Maui's neighboring islands plus spectacular sunsets make this romantic studio condo in Lahaina a place you'll want to return to again and again. Located on a reef-protected beach on Maui's sunny west side, this...

    Pool
    FREE CANCELLATION

    $290 to $493/night

  26. CONDOMINIUM
    Honua Kai-Hokulani #218

    Honua Kai-Hokulani #218

    Lahaina, HI

    Ocean and Resort views in North Ka'anapali. A brand new one bedroom condo at the Honua Kai in the Hokulani tower. Granite counter tops and stainless steel appliances make for an exceptionally polished look. In addition to the flat screen TV in the...

    Pool
    FREE CANCELLATION

    $348 to $669/night

  27. CONDOMINIUM
    Mahana Resort #617

    Mahana Resort #617

    Lahaina, HI

    Welcome to Mahana 617. This oceanfront one bedroom, one bath condo sleeps 2-4 and features stunning panoramic views of the ocean, beach and outer islands from the living room, dining area, bedroom, and lanai. The living room features a 47" HD TV,...

    Pool
    FREE CANCELLATION

    $319 to $638/night

  28. CONDOMINIUM
    Mahana Resort #1204

    Mahana Resort #1204

    Lahaina, HI

    Ocean front on North Ka'anapali beach. An ocean front bedroom allows for a greater view in this Deluxe unit that has been completely remodeled. A TV, VCR and DVD player in the bedroom have been provided for your entertainment. The bathroom features...

    Pool
    FREE CANCELLATION

    $325 to $606/night

  29. CONDOMINIUM
    Kaanapali Shores #159

    Kaanapali Shores #159

    Lahaina, HI

    Almost ocean front on Kaanapali Beach. Our 2 bedroom, 2 bath condo is one unit back from being direct ocean front. Being ground floor allows for easy access to pool and beach. Enjoy amazing Maui sunsets from our lanai. Tastefully furnished and ready...

    Pool
    FREE CANCELLATION

    $377 to $800/night

  30. CONDOMINIUM
    Maui Kaanapali Villas #E288

    Maui Kaanapali Villas #E288

    Lahaina, HI

    Ocean views in North Ka'anapali overlooking pool. This studio condo is located in the Emerald Building of the beautiful beach front resort: Maui Kaanapali Villas. Kitchen and bathroom remodeled March 2019. This second floor condo has stairs to its...

    Pool
    FREE CANCELLATION

    $220 to $377/night