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
    Honua Kai Konea 501

    Honua Kai Konea 501

    Kaanapali, HI

    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 home has 180 degree views and SUNSETS ALL YEAR LONG. Watch the Whales in...

    Pool Hot Tub

    $602 to $2,133/night

  2. CONDOMINIUM
    Waiohuli Beach Hale #D-117

    Waiohuli Beach Hale #D-117

    Kihei, HI

    Unit D-117 at Waiohuli Beach Hale is a ground floor, 1 bedroom, 1 bath unit with a partial ocean view. This very clean, nicely furnished unit features a walk out lanai to beautiful tropical gardens and the large ocean front, solar heated pool. The...

    Pool
    FREE CANCELLATION

    $157 to $277/night

  3. CONDOMINIUM
    Kulakane 307

    Kulakane 307

    Lahaina, HI

    You can't get closer to the ocean than this unless your on a boat. The property is beautiful and well kept. Watch the whales December through April from your lanai. Sunsets every night. Conch blowing at sunset. Swimming, snorkeling and relaxing in...

    Pool
    FREE CANCELLATION

    $214 to $906/night

  4. CONDOMINIUM
    Wailea Ekolu 1606

    Wailea Ekolu 1606

    Kihei, HI

    Located in beautiful Wailea, this 2bd 2ba condo is on the top floor and boasts high ceilings and a gorgeous ocean view. Visting with a larger group? We have another unit in the same building! Make sure to ask us the availability for booking 1604...

    Pool
    FREE CANCELLATION

    $281 to $874/night

  5. CONDOMINIUM
    Maui Kai 601

    Maui Kai 601

    Lahaina, HI

    Enjoy unbeatable panoramic views from this highly desirable 6th floor oceanfront corner unit on the Kaanapali coast. You can’t get any closer to the ocean than this resort! Watch gorgeous sunsets over Molokai and Lanai every day from the comfort...

    Pool
    FREE CANCELLATION

    $249 to $688/night

  6. CONDOMINIUM
    Kaanapali Shores 403

    Kaanapali Shores 403

    Lahaina, HI

    Relax on our 4th floor lanai, overlooking the ocean, well-kept grounds and pool at Kaanapali Shores! Kaanapali Shores resort is located on the beach in North Kaanapali. Unit 403 lanai has views of the ocean,spectacular sunsets, and whales in...

    Pool
    FREE CANCELLATION

    $374 to $1,206/night

  7. CONDOMINIUM
    Kahana Sunset E4

    Kahana Sunset E4

    Lahaina, HI

    Come and enjoy the amazing views and sunsets at Kahana Sunset Oceanfront Condos!! This beautiful 2 bedroom, 2 bathroom condo with breathtaking views of the ocean provides everything you need for your vacation in paradise. With a fully equipped...

    Pool
    FREE CANCELLATION

    $224 to $500/night

  8. CONDOMINIUM
    Keawakapu 208

    Keawakapu 208

    Kihei, HI

    Brand New 2br 809 Sq Ft Condo, 3 Minute Walk To Beaches~Ocean And Haleakala Views !! Gorgeous ocean views, from our newly renovated, newly decorated, 2 Bedroom, 1 Bath Condo, just a 3 minute walk to the nicest Beach on Maui, Keawakapu ! Relax on the...

    FREE CANCELLATION

    $149 to $438/night

  9. CONDOMINIUM
    Kahana Reef 103

    Kahana Reef 103

    Lahaina, HI

    Come see the whales with us this winter! Imagine yourself sitting on the lanai, sipping on a Mai Tai and watching the sun fall into the Pacific Ocean right in between Lanai & Molokai. Kahana Reef sits right on the ocean in Kahana in between Kapalua...

    Pool
    FREE CANCELLATION

    $139 to $635/night

  10. 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

  11. CONDOMINIUM
    Maui Kamaole #A-207

    Maui Kamaole #A-207

    Kihei, HI

    Maui Kamaole #A207 is a beautifully furnished and decorated ocean view condo that has all the amenities to make your vacation in paradise perfect. The Lanai furniture is comfortable and is the best spot to start your morning and end an evening. It...

    Pool Hot Tub
    FREE CANCELLATION

    $261 to $451/night

  12. CONDOMINIUM
    Honua Kai Konea 643

    Honua Kai Konea 643

    Kaanapali, HI

    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 in winter and the tours boats passing by...

    Pool Hot Tub

    $495 to $1,574/night

  13. CONDOMINIUM
    Maui Banyan #B-101

    Maui Banyan #B-101

    Kihei, HI

    This condo has a 40% discount already applied to the rate and will not accept additional promotions. Welcome to Maui Banyan B-101. This unit is new to Maui Condo and Home, but it has a long standing among past guests. There were pages of terrific...

    Pool Hot Tub
    FREE CANCELLATION

    $235 to $491/night

  14. CONDOMINIUM
    Papakea A108

    Papakea A108

    Lahaina, HI

    Enjoy the sunsets from your living room and lanai and sleep to the sounds of the surf all night. Watch the whales from your lanai! Enjoy spectacular, panoramic views of the blue Pacific and the islands of Lana’i and Moloka’i. Hawaiian...

    Pool

    $258 to $381/night

  15. CONDOMINIUM
    Maui Eldorado Condo A202

    Maui Eldorado Condo A202

    Kaanapali, HI

    Enjoy the quiet and privacy of a large second story one bedroom, with spectacular ocean and golf course views at Maui Eldorado, Kaanapali Maui. One bedroom with 2 Queen size beds, new carpet and sofa with 2 recliners. The spacious lanai extends the...

    Pool
    FREE CANCELLATION

    $213 to $596/night

  16. CONDOMINIUM
    Kona Plaza#402

    Kona Plaza#402

    Kailua Kona, HI

    ***New Property In Vacation Rental Inventory As Of June 2018.*** Knutson & Associates Property Management is proud to be newly representing Kona Plaza#402. Welcome to the listing page of Kona Plaza#402. It's amazing location puts you right in...

    Pool
    FREE CANCELLATION

    $257 to $267/night

  17. CONDOMINIUM
    Maui Eldorado Condo F201

    Maui Eldorado Condo F201

    Kaanapali, HI

    Super upstairs CORNER unit one bedroom 1000 sq ft TWO bathroom with wrap around 200 sq ft of covered lanai, perfect for couples of families. Conveniently located, walk to Whaler's Village shops, restaurants from this. Enjoy Maui's ONLY beachfront...

    Pool
    FREE CANCELLATION

    $220 to $596/night

  18. CONDOMINIUM
    Hololani #A-202

    Hololani #A-202

    Lahaina, HI

    See https://www.westmauicondos.com/maintenance-and-construction-schedule for resort improvement projects starting July 2019 This second floor condo in Kahana has spectacular ocean front views and has a television in the guest bedroom. The guest...

    Pool
    FREE CANCELLATION

    $232 to $532/night

  19. CONDOMINIUM
    Pohailani 128

    Pohailani 128

    Lahaina, HI

    Relax in this beautiful professionally decorated exquisite West Maui Condo. Total luxury at an affordable price ! Lahaina*Kaanapali*KAHANA*Napili*Kapalua -West MAUI HOT SPOTS Located in KAHANA (3 miles north of Kaanapali) in the center of West...

    Pool

    $178 to $228/night

  20. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club Townhouse #185

    Keauhou Kona Surf and Racquet Club Townhouse #185

    Kailua Kona, HI

    Townhome#185 is an amazing DIRECT oceanfront property at a amazing value. Enjoy the privacy of a townhome. Living area & Kitchen downstairs, bedrooms upstairs. Wifi, Beachgear available to you for your convenience. The Keauhou Surf and Racquet Club...

    Pool
    FREE CANCELLATION

    $390 to $404/night

  21. 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

  22. VILLA
    Bay Villa 32B2 Gold Ocean View

    Bay Villa 32B2 Gold Ocean View

    Kapalua, HI

    Lovely Italian Design features new living room and dining room furnishings, magnificent ocean views, 2 master suites and 3 baths. This professionally designed lovely retreat is synonymous with island pleasure. The perfect Rx for all of life's little...

    Pool

    $531 to $969/night

  23. VILLA
    Bay Villa 15G5 Ocean View

    Bay Villa 15G5 Ocean View

    Kapalua, HI

    These amenities are included for your comfort and convenience: **no need to scramble for a grocery store when you arrive. Send us your list. We'll make sure your villa is well stocked with your favorites! You pay only for the cost of groceries....

    Pool

    $294 to $531/night

  24. HOUSE
    Piko Nani

    Piko Nani

    Kailua Kona, HI

    Piko Nani “Hilltop Beauty” sits high on a knoll at the very top of O'oma Plantation, a newer subdivision of 19 estate-sized, 2-acre parcels. This quiet, supremely private home is perfect for a serene getaway. The elegantly finished interior of...

    Pool

    $555 to $759/night

  25. CONDOMINIUM
    Alii Villas 340

    Alii Villas 340

    Kailua Kona, HI

    This top floor Alii Villas condo is a perfect fit for anyone's vacation. Unit#340 is very well maintained, and we can assure you will have an amazing time in this fantastic, extremely affordable condo. Wifi included. There is a Queen sized bed in...

    Pool
    FREE CANCELLATION

    $211 to $276/night

  26. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Enjoy unbeatable panoramic views from this highly desirable 6th floor oceanfront unit on the Kaanapali coast. You can’t get any closer to the ocean than this resort! Watch gorgeous sunsets over Molokai and Lanai every day from the comfort of your...

    Pool Hot Tub
    FREE CANCELLATION

    $224 to $630/night

  27. COTTAGE
    2 Charming Cottages on the Ocean

    2 Charming Cottages on the Ocean

    Kamuela, HI

    Offering an idyllic oceanfront setting in the town of Puako, this rental sleeps up to six guests between the 1BR cottage and a separate studio. Perfect for groups seeking extra privacy, this charming seaside compound boasts unobstructed views of the...

    FREE CANCELLATION

    $526 to $1,455/night

  28. CONDOMINIUM
    Kauhale Makai #330

    Kauhale Makai #330

    Kihei, HI

    Hawaiian for "Village By The Sea," the Kauhale Makai complex is an oceanfront property located in Kihei. This is one of a few buildings in the area with central air conditioning - not window units. This condo stays as cool as you like it. Kihei is...

    Pool
    FREE CANCELLATION

    $150 to $254/night

  29. CONDOMINIUM
    B-801: Hale Ohana Ko Olina Beach Villa

    B-801: Hale Ohana Ko Olina Beach Villa

    Kapolei, HI

    Experience the ultimate in oceanfront resort living in this beautiful and spacious vacation home located in the Beach Villas at Ko Olina! This 3 BR, 3 BA luxury villa on the 8th floor of the Beach Tower is conveniently located just 20 miles from...

    Pool Hot Tub

    $717 to $1,784/night

  30. CONDOMINIUM
    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit H4 is deluxe in every sense. H4 is an ideally located ground floor unit, approximately 5 steps from the white sandy beach. This exceptional unit features a full kitchen, second bedroom and bath. Enjoy the ocean views and Maui's...

    Pool
    FREE CANCELLATION

    $416 to $664/night