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
    Kahana Villa E111

    Kahana Villa E111

    Lahaina, HI

    Elegant, completely REMODELED 2 bedroom, 2 bathroom condo available now at Kahana Villa! The kitchen and bath both have new granite counter tops. The kitchen is fully stocked with glasses, pots, pans, cooking utensils, plates, bowls and everything...

    Pool Hot Tub
    FREE CANCELLATION

    $225 to $384/night

  2. CONDOMINIUM
    Cliffs 4205

    Cliffs 4205

    Princeville, HI

    This beautiful Kauai vacation rental is equipped with all of the modern luxury you’ll need, while also providing an easy, tranquil vacation-getaway on Kauai's paradisical north shore in Princeville. Stare into the expanse of the deep blue Pacific...

    Pool Hot Tub

    $235 to $301/night

  3. HOUSE
    Hahalua Hale

    Hahalua Hale

    Kailua Kona, HI

    Welcome to "Hahalua Hale" (House of the Manta Ray) located in a quiet gate community. Located at a perfect coffee growing elevation that receives those cool tropical Hawaiian breezes, this magnificent, one-of-kind, architectural showpiece sited for...

    Pool Hot Tub

    $1,261 to $1,664/night

  4. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    Lahaina, HI

    This rarely-available top-floor penthouse condominium is the ultimate in luxury living. Konea 743 boasts amazing ocean views of Maui and the surrounding islands. This spacious suite includes two bedroom, two full baths and a sofa-bed to accommodate...

    Pool Hot Tub
    FREE CANCELLATION

    $513 to $988/night

  5. HOUSE
    Alii Point #7 Oceanfront

    Alii Point #7 Oceanfront

    Kailua Kona, HI

    For a virtual tour of this property scroll down to the bottom of the text and click on the link. If viewing on vrbo click on the last picture and then the arrow to the right of the picture for the Virtual Tour. Private Oceanfront custom home with...

    Pool Hot Tub

    $668 to $846/night

  6. CONDOMINIUM
    Wailea Grand Champion, #148

    Wailea Grand Champion, #148

    Wailea, HI

    Wailea Grand Champions Golf Villas is a modern property located between the Wailea Blue Golf Course and the Wailea Tennis Club. This quiet low density development consists of twenty mostly two-story buildings set amongst lush tropical landscaping...

    Pool Hot Tub

    $201 to $549/night

  7. 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

  8. CONDOMINIUM
    Kauai Beach Villas 1 Bedroom

    Kauai Beach Villas 1 Bedroom

    Lihue, HI

    Kauai Beach Villas Booking stays under 3 days may be possible. Please inquire for more information The ever so charming Kauai Beach Villas is located in Lihue Hawaii and is nicknamed the “Coconut Coast”. This resort is conveniently, just...

    Pool Hot Tub

    $209/night

  9. CONDOMINIUM
    Cliffs 9201

    Cliffs 9201

    Princeville, HI

    Enjoy the cooling trade winds while watching the dolphins and whales (depending on season) frolicking in front of you as you are lounging on your private oceanfront lanai (patio). This very comfortable condo provides spectacular sunrises and sunsets...

    Pool Hot Tub

    $253 to $271/night

  10. CONDOMINIUM
    Sugar Beach Resort, #330

    Sugar Beach Resort, #330

    Kihei, HI

    Unit #330 at Sugar Beach Resort is a nicely decorated third floor oceanfront unit that comes equipped with a king bed, queen sofa sleeper, 2 TV's, each with it's own DVD player, 2 cordless phones, wireless Internet, CD player, all new furniture,...

    Pool Hot Tub

    $202 to $387/night

  11. CONDOMINIUM
    Sugar Beach Resort, #121

    Sugar Beach Resort, #121

    Kihei, HI

    Unit #121 at Sugar Beach Resort is a ground floor oceanfront unit that comes equipped with a king bed, queen size sofa sleeper, DVD/VCR and CD player. Sugar Beach Resort is a tranquil beachfront condominium resort located in North Kihei offering...

    Pool Hot Tub

    $202 to $387/night

  12. CONDOMINIUM
    Noelani 211- Modern, Upscale Ocean Front Condo

    Noelani 211- Modern, Upscale Ocean Front Condo

    Lahaina, HI

    Noelani is an OCEANFRONT property on lush landscaped grounds, reminiscent of Old Hawaii. A quiet low rise development of fifty units next to S Turns, a popular sandy beach. The property features two pools, one of which is a lap pool! There is a...

    Pool Hot Tub
    FREE CANCELLATION

    $179 to $320/night

  13. CONDOMINIUM
    Honua Kai Konea 224

    Honua Kai Konea 224

    Lahaina, HI

    This luxury Honua Kai one bedroom located in the 'Konea Tower' features everything you need to make your Hawaiian vacation truly enjoyable! We provide you with those extra amenities that make a difference, including comfortable beach chairs, beach...

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $401/night

  14. 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 $1,727/night

  15. CONDOMINIUM
    Fairway Villas A-31

    Fairway Villas A-31

    WAIKOLOA, HI

    Outstanding 2 bedroom, 2 bath Top Floor “Penthouse” condo with spectacular view of the 6th fairway of the Waikoloa Beach Golf Course, Mauna Kea, and the Kohala mountains. This contemporary Hawaiian Plantation designed condominium gives you space...

    Pool Hot Tub

    $194 to $244/night

  16. CONDOMINIUM
    Sugar Beach Resort, #130

    Sugar Beach Resort, #130

    Kihei, HI

    Unit #130 at Sugar Beach Resort is a ground floor, oceanfront condo with a newly remodeled kitchen complete with granite counter tops. This unit comes equipped with a king bed, queen size sofa sleeper, VCR, CD player and FREE wireless broadband...

    Pool Hot Tub

    $178 to $387/night

  17. 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

    $766 to $846/night

  18. CONDOMINIUM
    Pali Ke Kua 107

    Pali Ke Kua 107

    Princeville, HI

    Enjoy the magnificent ocean views & be lulled by the sound of the waves below at Pali Ke Kua 107, located in the prestigious Princeville resort on the north shore of Kauai. Ocean views abound from the Living room, kitchen, dining area & lanai...

    Pool Hot Tub

    $319 to $392/night

  19. 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

  20. CONDOMINIUM
    Cliffs 6201

    Cliffs 6201

    Princeville, HI

    Standing on your lanai at The Cliffs #6201, you have a 180 degree unfettered view of the spectacular deep blue waters of Kauai’s northern coastline, with serene quiet only broken by the wild geese and other tropical migratory birds sailing by in...

    Pool Hot Tub

    $211 to $235/night

  21. CONDOMINIUM
    Kamahana 18

    Kamahana 18

    Princeville, HI

    Situated near the 6th fairway of the Makai Golf Course, this beautiful Kauai vacation rental is perfect for the golf enthusiast or anyone looking for a great view. Enjoy breathtaking views of the ocean, golf course, and Kilauea lighthouse while...

    Pool Hot Tub

    $223 to $277/night

  22. HOUSE
    Mauna Kai 4

    Mauna Kai 4

    Princeville, HI

    Two bedroom/two bathroom condominium near the Westin Hotel. The Mauna Kai complex has one of the largest swimming pools in Princeville. The unit offers two bedrooms downstairs, one with a queen bed and the other a double, with a shared bathroom. The...

    Pool Hot Tub

    $235 to $283/night

  23. CONDOMINIUM
    Cliffs 5201

    Cliffs 5201

    Princeville, HI

    This beautiful Kauai vacation rental is perfect for two. If you are looking for a comfortable stay in paradise on the second floor, you have found it. Enjoy the fully equipped kitchen, sip a cool drink on the lanai (patio) or take a short stroll...

    Pool Hot Tub

    $211 to $259/night

  24. CONDOMINIUM
    Sugar Beach Resort, #414

    Sugar Beach Resort, #414

    Kihei, HI

    A note from the owner: This highly sought after, newly renovated, ocean front corner unit has a view of the swimming pool, BBQ area and of beautiful Sugar Beach extending in both directions. This unit is on the 4th floor and has one bedroom, a fully...

    Pool Hot Tub

    $202 to $387/night

  25. CONDOMINIUM
    Wailea Elua, #2003

    Wailea Elua, #2003

    Wailea, HI

    A note from the owner: You will love the elegance of this remodeled one-bedroom, two-bath Elua condo. You can spread out, relax and truly enjoy your stay in paradise. Our large lanai, living room and master bedroom are ocean facing, with a...

    Pool Hot Tub

    $448 to $823/night

  26. CONDOMINIUM
    Maui Eldorado I204/205 2Bdrm 2Bath

    Maui Eldorado I204/205 2Bdrm 2Bath

    Lahaina, HI

    Picture yourself sitting on one of your two private lanai's while overlooking the 4th green of the Royal Golf Course at Kaanapali and experiencing views of the blue Pacific ocean, sunsets, winter whale watching and the island of Molokai. Our...

    Pool Hot Tub
    FREE CANCELLATION

    $383 to $551/night

  27. 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

  28. 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

  29. 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

  30. 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