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. HOUSE
    Sands of Kahana 366

    Sands of Kahana 366

    LAHAINA, HI

    Sands of Kahana is ideally situated on Maui’s world famous west coast between Kaanapali and Kapalua. This fully furnished, three bedroom, two bathroom oceanfront condominium comes with air-conditioning! Three bedroom oceanfront, unit 366 is a...

    Pool Hot Tub

    $501 to $619/night

  2. HOUSE
    Heeia Bay Hale

    Heeia Bay Hale

    Kailua Kona, HI

    Welcome to the listing page of Heeia Bay Hale! A Brand New Vacation Rental as of October 2018. This wonderful 2 story home in Keauhou is WALKING DISTANCE TO HEEIA BAY!! This private & spacious 3 bedroom, 3.25 bath multi-level Hawaiian style beach...

    Pool
    FREE CANCELLATION

    $501 to $773/night

  3. HOUSE
    Sands Of Kahana 356

    Sands Of Kahana 356

    Lahaina, HI

    Grasp the beautiful sunsets and rainbows from this very spacious three bedroom, two bathroom condominium. This unit is one of the few 3 bedroom units at the Sands of Kahana that has air conditioning! Ocean views and vivid rainbow skies are visible...

    Pool Hot Tub

    $501 to $557/night

  4. HOUSE
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Experience the good life 'Hawaiian style' as you sit on your private lanai watching the sunset and enjoying the balmy trade winds. This striking 3 bedroom, 3 bathroom penthouse has one-of-a kind views of Molokai and Lanai. It is a beautiful, newly...

    Pool Hot Tub

    $501 to $557/night

  5. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    This brand-new beautiful new 5th floor listing at the Mahana at Kaanapali boasts gorgeous views of both the tranquil blue Pacific Ocean AND the lush West Maui Mountains. This property is extremely close to the water, you can literally sit in the 5th...

    Pool Hot Tub
    FREE CANCELLATION

    $499 to $1,753/night

  6. HOUSE
    Ocean Tree House w/ Lanai & Yard- Walk to Beach

    Ocean Tree House w/ Lanai & Yard- Walk to Beach

    Kailua, HI

    Located in the upscale neighborhood of Lanikai, this 3BR/2BA is affectionately named Ocean Tree House and is within strolling distance to Lanikai Beach — regarded as one of the world's most beautiful top beaches, with its flour-soft white sands,...

    FREE CANCELLATION

    $496 to $803/night

  7. 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...

    Pool Hot Tub

    $495 to $1,620/night

  8. CONDOMINIUM
    Wailea Elua Unit #0202

    Wailea Elua Unit #0202

    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

    $494 to $1,065/night

  9. VILLA
    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua Bay Villa 31G4 Gold Ocean View

    Kapalua, HI

    This luxurious Island Villa is uniquely positioned to offer nice ocean views! The perfect Rx for leaving your every care behind. Surround yourself with rare exotic wood cabinetry, new granite counter tops and new stainless steel appliances, Cool...

    $494 to $969/night

  10. VILLA
    Kapalua Ridge Villa 1214 Gold Ocean View

    Kapalua Ridge Villa 1214 Gold Ocean View

    Kapalua, HI

    Contact Manager about last minute Christmas Special for 2018! This luxurious retreat will spoil you forever. You’ll feel like you’re on top of the world as you take in spectacular views of the Pacific Ocean and the lush green landscape that...

    Pool

    $494 to $856/night

  11. VILLA
    Kapalua Bay Villa 30B1 Gold Ocean Front

    Kapalua Bay Villa 30B1 Gold Ocean Front

    Kapalua, HI

    Renovation Complete! This unique oceanfront location is situated on one of the most beautiful parts of the West Maui coast, Fresh out of renovation and rich with every imaginable upgrade. Every surface has been covered in natural stone, glass...

    Pool

    $494 to $781/night

  12. VILLA
    Kapalua Ridge Villa 1112 Gold Ocean View

    Kapalua Ridge Villa 1112 Gold 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...

    $494 to $869/night

  13. CONDOMINIUM
    Wailea Elua #701

    Wailea Elua #701

    Wailea, 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

    $493 to $922/night

  14. HOUSE
    Honua Kai-Konea #539

    Honua Kai-Konea #539

    Lahaina, HI

    Ocean views from the Konea tower in North Ka'anapali with a wrap-around corner Lanai. The stainless steel appliances, granite counter tops and modern decor compliment this brand new 2 bedroom condo at a brand new resort. In addition to the flat...

    Pool
    FREE CANCELLATION

    $493 to $1,467/night

  15. HOUSE
    Kapalua Golf Villas #12T5

    Kapalua Golf Villas #12T5

    Kapalua, HI

    Relax and enjoy the tranquil setting of this luxurious Kapalua Golf Villa. Let the gorgeous greenery captivate and soothe your soul. This unit has been remodeled with only top of the line materials and furnishings and is well apointed. Spend your...

    Pool
    FREE CANCELLATION

    $493 to $626/night

  16. 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...

    Hot Tub Pets OK
    FREE CANCELLATION

    $493 to $782/night

  17. HOUSE
    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

    $493 to $800/night

  18. CONDOMINIUM
    Papakea L405

    Papakea L405

    Lahaina, HI

    You will not find a nicer penthouse oceanfront unit at the Papakea Resort. From your lanai and the master bedroom, you can watch the whales play in the ocean seasonally and see the honu (turtles) swim all year round. This unit has an oceanfront...

    Pool Hot Tub

    $491 to $737/night

  19. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    One of the nicest penthouse units at Papakea Resort. From your lanai and the master bedroom, watch the whales play and the honu (turtles) swim. The KING bed in master bedroom allows you to sleep to the sounds of the ocean just 25 feet away. The...

    Pool Hot Tub

    $491 to $707/night

  20. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Spend your dream vacation on Maui at the Whaler on beautiful Kaanapali beach! Enjoy stunning West Maui sunsets and gorgeously landscaped grounds! Relax on the lanai with a cup of coffee or a cocktail where you can see from Mauka to Makai (from...

    Pool Hot Tub
    FREE CANCELLATION

    $491 to $1,420/night

  21. CONDOMINIUM
    Hanalei Colony Resort I1

    Hanalei Colony Resort I1

    Hanalei, HI

    Wow, you'll have this gorgeous north shore beach all to yourselves!!! July 1 marks the date our Hanalei Colony Resort rentals re-open to guests - and for a limited time we'll have a special rate available. For a year now, the North Shore past...

    Pool
    FREE CANCELLATION

    $488 to $581/night

  22. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Wow, you'll have this fabulous north shore beach all to yourselves!!! July 1 marks the date our Hanalei Colony Resort rentals re-open to guests - and for a limited time we'll have a special rate available. For a year now, the North Shore past...

    Pool
    FREE CANCELLATION

    $488 to $581/night

  23. HOUSE
    Sands of Kahana #292

    Sands of Kahana #292

    Lahaina, HI

    9th Floor Ocean Front 3 bedroom, 3 bath Penthouse at the beautiful Sands of Kahana with exquisite views of the neighboring islands. This spacious 3 bedroom condo allows for plenty of room and seating areas for the entire family. A fully equipped...

    Pool
    FREE CANCELLATION

    $487 to $1,183/night

  24. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Beautifully appointed "like new" 2 bedroom 2.5 bath oceanfront home with pool. Gourmet kitchen and huge deck for tanning, dining & sunset cocktails. Upstairs master has shower & hot tub. Sliding doors disappear into walls for the ultimate "on the...

    Pool

    $486 to $608/night

  25. CONDOMINIUM
    Hale Alii Ko Olina Beach Villa (O924)

    Hale Alii Ko Olina Beach Villa (O924)

    Kapolei, HI

    LIVE CALENDAR: If the calendar shows as available, the property IS available and can be booked INSTANTLY online 24/7. This listing and availability are updated in real-time. You can click/tap the calendar tab to see availability. Feel free to...

    Pool Hot Tub

    $485 to $1,204/night

  26. CONDOMINIUM
    Ko Olina Beach Villa (O425)

    Ko Olina Beach Villa (O425)

    Kapolei, HI

    LIVE CALENDAR If the calendar shows as available, the property is not reserved and can be booked instantly online. This listing is updated in real-time. Please click the calendar tab to see availability. This Villa requires a minimum 6 night stay....

    Pool

    $485 to $1,204/night

  27. CONDOMINIUM
    Hale Mahina Ko Olina Beach Villa (O904)

    Hale Mahina Ko Olina Beach Villa (O904)

    Kapolei, HI

    LIVE CALENDAR: If the calendar shows as available, the property IS available and can be booked INSTANTLY online 24/7. This listing and availability are updated in real-time. You can click/tap the calendar tab to see availability. Feel free to...

    Pool Hot Tub

    $485 to $1,204/night

  28. CONDOMINIUM
    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    Kapolei, HI

    LIVE CALENDAR: If the calendar shows as available, the property IS available and can be booked INSTANTLY online 24/7. This listing and availability are updated in real-time. You can click/tap the calendar tab to see availability. Feel free to...

    Pool Hot Tub

    $485 to $1,204/night

  29. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    Experience beach living in this beautiful vacation home on Puako Beach. This private residence is located right across the street from the ocean. Great place to kayak and snorkel in one of the best snorkeling spots on the Big Island. Or bask with...

    FREE CANCELLATION

    $485 to $652/night

  30. CONDOMINIUM
    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    Kapolei, HI

    LIVE CALENDAR If the calendar shows as available, the property is not reserved and can be booked instantly online. This listing is updated in real-time. Please click the calendar tab to see availability. This Villa requires a minimum 6 night stay....

    Pool Hot Tub

    $485 to $1,204/night