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. APARTMENT
    Golf Course Views & Private! Lovely Renovated 2 Bed/2 Bath- Elima Lani 207

    Golf Course Views & Private! Lovely Renovated 2 Bed/...

    Waikoloa, HI

     This stunning 2 bedroom, 2 bathroom condo with gorgeous golf course views has everything you need for a relaxing vacation. The unit has been exquisitely remodeled from top to bottom. Beautiful new floors, cabinets and counters along with all brand...

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $213/night

  2. CONDOMINIUM
    Perfect for Your Vacation!- 2 Bed/2 Bath on the Golf Course

    Perfect for Your Vacation!- 2 Bed/2 Bath on the Golf Cou...

    Waikoloa, HI

     This is an adorable, updated 2 bedroom 2 bath condo located in Waikoloa Village with fairway view. Updated furnishings with great accommodation for the travelers to Hawaii!  There's a fully furnished kitchen, two full bathrooms and two great...

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $183/night

  3. CONDOMINIUM
    Aina Nalu K 205

    Aina Nalu K 205

    lahaina, HI

    AINA NALU K-205 Welcomes you with Aloha...This unique condo, in the heart of Old Lahaina Town, is a perfect vacation spot!K-205 was remodeled with the touch of ALOHA in 2017.Included in our fabulous price are many owner-supplied extras such as:•...

    Pool Hot Tub
    FREE CANCELLATION

    $133 to $239/night

  4. HOUSE
    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    Kailua Kona, HI

    Known as ‘Aniani Hale,’ or Glass House, this stunning 4BR/4.5BA home is situated just above the heart of Kailua-Kona. Elevated 700 feet above sea level, your beautiful island getaway boasts refreshing trade winds from the west and mountain...

    Pool Hot Tub
    FREE CANCELLATION

    $565 to $869/night

  5. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    AINA NALU A-201 Welcomes you with Aloha...This unique condo in the heart of Old Lahaina Town is a perfect vacation spot!A-201 has been remodeled with a decor that speaks "ALOHA"Included in our fabulous price are many owner-supplied extras such...

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $371/night

  6. VILLA
    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    Waikoloa, HI

    This Villa is in an excellent location right at one of the two lava rock pools that Waikoloa Beach Villas has to offer. The property is located on the ground floor which comes with many benefits. No stairs to climb, which makes bringing groceries...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $431/night

  7. CONDOMINIUM
    The Montage Kapalua Bay- Heliconia 2302- Ocean View Paradise!

    The Montage Kapalua Bay- Heliconia 2302- Ocean View Para...

    Kapalua, HI

    Beautiful 3 bedroom/3.5 bath plus Den Residence.Heliconia Residence at Residences at MontageThis beautiful 3 bedroom/3.5 bath plus Den home is situated in Building #2 at the Residences at Montage in beautiful Kapalua.Enjoy the ocean views from the...

    Pool Hot Tub

    $978 to $4,611/night

  8. CONDOMINIUM
    Honua kai- Konea 1026- 2 bedroom Partial Ocean View

    Honua kai- Konea 1026- 2 bedroom Partial Ocean View

    Lahaina, HI

    TOP FLOOR - OCEAN VIEW!OCEAN VIEWS FROM TWO BEDROOM PENTHOUSE LEVEL!NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the Konea building at Honua Kai. This condo overlooks the construction site. There may be noise and dust on...

    Pool Hot Tub

    $400 to $1,418/night

  9. DUPLEX
    Manoa Valley 3BR w/ Hot Tub & Lanai w/ Ocean View

    Manoa Valley 3BR w/ Hot Tub & Lanai w/ Ocean View

    Honolulu, HI

    Perched on a hill overlooking Honolulu City and the majestic Diamond Head volcano, this 3BR/2.5BA Manoa Valley duplex features gorgeous Craftsman touches and an expansive lanai that’s perfect for a barbecue.Striking stained glass and teak accents...

    Hot Tub Pets OK
    FREE CANCELLATION

    $444 to $1,527/night

  10. 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 $762/night

  11. CONDOMINIUM
    Palms at Wailea #1503

    Palms at Wailea #1503

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long white sandy shoreline. The Palms at Wailea is a gorgeous property; lush with tropical landscaping....

    Pool Hot Tub
    FREE CANCELLATION

    $418 to $585/night

  12. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Kamaole Beach III is just across the street from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property and tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  13. CONDOMINIUM
    Hear the Waves!! Honua Kai- Hokulani 306

    Hear the Waves!! Honua Kai- Hokulani 306

    Kaanapali, HI

    UPGRADED OCEAN/MOUNTAIN VIEW 2 bed/2 bath - GREAT VALUE!*This condo is so close to the beach you can hear the waves crashing!This 1240 Sq ft OCEAN VIEW condo has been upgraded with new DESIGNER FURNISHINGS, SMART TV and TRAVERTINE FLOORING...

    Pool Hot Tub

    $436 to $1,596/night

  14. CONDOMINIUM
    Kihei Bay Surf #126

    Kihei Bay Surf #126

    Kihei, HI

    Kihei Bay Surf is located in North Kihei across the street from the Whale Sanctuary and Kalepolepo Beach and an ancient Hawaiian fishpond. Each studio has a fully equipped kitchen and cable TV. In addition there is a large pool, hot tub, tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  15. CONDOMINIUM
    Kihei Bay Surf #226

    Kihei Bay Surf #226

    Kihei, HI

    The Kihei Bay Surf is located in North Kihei across the street from the Humpback Whale Marine Sanctuary and Kalepolepo Beach and an ancient Hawaiian fishpond. Each studio has a fully-equipped kitchen, Cable TV and can sleep from 2-3 people. In...

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  16. HOUSE
    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    Lahaina, HI

    This premium oceanfront Two Bedroom, Two Bath condo is conveniently located on the ground level. Master Bedroom has a King Bed with a private bathroom. Second Bedroom has a queen bed; and the living room has a queen sofa bed for the extra guests....

    Pool Hot Tub
    FREE CANCELLATION

    $516 to $620/night

  17. CONDOMINIUM
    Kihei Garden Estates #D-201

    Kihei Garden Estates #D-201

    Kihei, HI

    Kihei Garden Estates is a lovely property right across the street from Waiohuli Beach. Kihei Garden Estates boasts a family friendly gathering area, seating up to 25 people to your Bar-B-Q feast under the covered pavilion. Enjoy this full outdoor...

    Pool Hot Tub
    FREE CANCELLATION

    $139 to $231/night

  18. CONDOMINIUM
    Papakea A108

    Papakea A108

    Lahaina, HI

    This GROUND FLOOR, OCEANFRONT condo is just feet from ocean access. Completely remodeled kitchen, bathroom and living room, with queen size bed in the bedroom, and queen size convertible sofa bed in the living room. Relax with the 55" SMART blue...

    Pool Hot Tub

    $245 to $381/night

  19. CONDOMINIUM
    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2b

    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2...

    Kaanapali, HI

    Absolutely the MOST DESIRABLE 2 bedroom 2.5 bath condo in the entire complex.Konea 501 is the top unit of only 5 TWO BEDROOM ALI'I SUITES with DIRECT OCEAN VIEWS and private OUTDOOR KITCHENS. At 1620 Sq ft with a HUGE 415 Sq ft lanai this gorgeous...

    Pool Hot Tub

    $603 to $2,466/night

  20. HOUSE
    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Lahaina, HI

    Our Junior Suite on the TENTH Floor is spacious and well-appointed with a King Bed as well as a sofa bed for the occasional guest. You will find seating arrangements for relaxing and dining. There is plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  21. HOUSE
    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Kaanapali, HI

    Our Junior Suite is spacious and well-appointed with a Queen Bed and seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and personal items. The kitchen comes fully equipped with all the modern...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  22. CONDOMINIUM
    Maui Sunset #A-204

    Maui Sunset #A-204

    Kihei, HI

    Maui Sunset is a fabulous oceanfront property in Kihei that has lush tropical landscaping, large pool which is heated during the winter months, hot tub, gas grills, work out room and tennis courts out on the beach for your use. Guests return here...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $266/night

  23. CONDOMINIUM
    Honua Kai- Konea 643- Two Bed Ocean Views! 2b/2b

    Honua Kai- Konea 643- Two Bed Ocean Views! 2b/2b

    Kaanapali, HI

    OCEAN VIEW CENTER COURTYARD GREAT DEAL!!!This great sixth floor 1315 square foot condo is in the interior courtyard of the Konea building with wonderful ocean views from the spacious lanai. Enjoy your morning coffee while watching the whales play...

    Pool Hot Tub

    $483 to $1,704/night

  24. HOUSE
    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Lahaina, HI

    Lovely Oceanfront Junior Suite that features one large room with fully equipped kitchen and bath. Queen-size bed (Sleeps 2). Can accommodate 3 people with added roll-away. Located on the shores of Ka‘anapali Beach in West Maui, Maui Kai is an...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  25. HOUSE
    1 Bedroom Oceanfront #804

    1 Bedroom Oceanfront #804

    Lahaina, HI

    Our One Bedroom Oceanfront unit is spacious and well-appointed with a King Bed in the bedroom and sofa sleeper in the living room. This condo will accommodate four persons. You will find seating arrangements for relaxing, dining, and there is...

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  26. CONDOMINIUM
    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali Shores- 259- So close to the Beach!! 2b/2b

    Kaanapali, HI

    Best Ocean View Condo At Kaanapali Shores and JUST RENOVATED!This amazing condo has just been updated with new Luxury Vinyl Plank Flooring throughout and new modern furnishings including a great new Sofa/sleeper with brand new 6" mattress! (New...

    Pool Hot Tub

    $287 to $1,190/night

  27. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    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

    $235 to $370/night

  28. CONDOMINIUM
    Fairway Villas Waikoloa O21

    Fairway Villas Waikoloa O21

    Waikoloa, HI

    Designer furnishings, tropical artwork, luxurious linens and toiletries! Outstanding accommodations await you. Conveniently located parking to condo and elevator. Well-appointed, spacious master bedroom features a comfy Cal-king size bed, with...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $464/night

  29. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Your dream Maui vacation awaits! Kamaole Sands 8-203 is on the second floor of building 8 in one of the most sought-after complexes in South Maui. This unit has been newly updated and has a brand new sofa sleeper in the living area and King mattress...

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $374/night

  30. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Thoughtfully designed with your comfort in mind, Hale Nui will exceed your expectations! After a long, arduous flight, each guest will feel embraced upon entering this exquisite, spacious home and everyone will immediately marvel at the panoramic...

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night