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
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Indulge yourself in the ultimate island style luxury at the Big Island of Hawaii’s most exclusive retreat, Kauhale Pilialoha. Experience breathtaking sunsets, enjoy the natural beauty of Hawaii from the ultimate poolside lanai perched on the...

    Pool Hot Tub

    $17,975 to $27,561/night

  2. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Hapuna Beach house description Welcome to Kalina at the High Bluffs of Mauna Kea Located on Kohala Coast on the Big Island of Hawaii, this luxurious private home is just a short golf cart ride away from the premier Mauna Kea Golf Course. It is...

    Pool Hot Tub

    $4,524 to $4,955/night

  3. 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

  4. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    'Kona Bubbles' is a absolute spectacular property that Knutson & Associates is extremely proud to be newly representing as of November 2018. A gorgeous home in gated Meilani View Estates with ocean views just above Kailua Kona. Recently finished in...

    Pool
    FREE CANCELLATION

    $1,322 to $1,395/night

  5. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Welcome to Hale Lani! This gorgeous house is a BRAND NEW VACATION RENTAL that Knutson & Associates Management is proud to represent. Hale Lani is the perfect spot to host a unforgettable Hawaii Vacation. With 4 bedrooms, and a capacity to sleep 14,...

    Pool
    FREE CANCELLATION

    $1,170 to $1,534/night

  6. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Sweeping Ocean Views & Separate Ohana. Rare 4 bedroom - Wai'ula'ula at Mauna Kea.Step into a dream at an exceptional four-bedroom ocean-view rental at Wai'ula'ula within the Mauna Kea Resort.At this single level brand new home, you will find a...

    Pool Hot Tub

    $1,168 to $2,876/night

  7. 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

  8. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kailua Kona, HI

    What is better than a Hawaiian sunset over the ocean? A sunset over the ocean that you can take in from the privacy of your tropical home-away-from-home! With nearly 5,000 square feet of indoor/outdoor living space, including a lanai with a pool...

    Pool

    $689 to $1,678/night

  9. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $687 to $1,668/night

  10. 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 $826/night

  11. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    We welcome you to stay at our private luxury home (Ono Hale) in the lush hills above historic Kailua Kona. Located just minutes from town and Kona’s beautiful sandy beaches. Cool and quiet. Ono Hale is situated on a very private lot on a quiet...

    Pool
    FREE CANCELLATION

    $525/night

  12. 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

    $467 to $774/night

  13. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Mauna Kea condo description Rare 3BR * Sleeps 6 * Panoramic Ocean Views * On 4th Fairway * Amenity Cards Available with fee*  Kumulani G-1, our 3-bedroom, 2-bathroom condominium home in the world-famous Mauna Kea Resort, has an Ocean view and...

    Pool Hot Tub

    $342 to $646/night

  14. CONDOMINIUM
    Honua Kai Hokulani 316 1BR

    Honua Kai Hokulani 316 1BR

    Lahaina, HI

    Suite 316 is located on the 3rd floor in the south building, called HOKULANI. This 1 bedroom/1bath unit is spacious at 700 square feet, plus a 145 square feet lanai. The suite is south facing and enjoys both ocean and mountain views. Being a...

    Pool Hot Tub
    FREE CANCELLATION

    $328 to $474/night

  15. CONDOMINIUM
    Noelani #110

    Noelani #110

    Lahaina, HI

    Not one, but two oceanfront pools and a Jacuzzi, what more can you ask for? Unit 110 is a ground floor unit with washer and dryer. New kitchen cabinets and counter tops. You'll love to just walking out from your private lanai right into the...

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $426/night

  16. CONDOMINIUM
    Nohonani 405

    Nohonani 405

    Lahaina, HI

    Nohonani 405 is a beautiful two bedroom one and a half bath unit on the fourth floor, with vaulted ceilings and a breathtaking ocean view. Ocean views can be seen from the kitchen, dining areas, living room and master bedroom. As with all the...

    Pool
    FREE CANCELLATION

    $274 to $403/night

  17. CONDOMINIUM
    Kuleana 614 1 Bdrm

    Kuleana 614 1 Bdrm

    Lahaina, HI

    The ultimate in luxury awaits at our completely remodeled and refurnished 1 bedroom, 1 bathroom oceanfront condo. Just steps from the water, this truly exceptional suite offers spectacular unobstructed ocean and sunset views from the lanai and...

    Pool
    FREE CANCELLATION

    $251 to $346/night

  18. 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

    $193 to $630/night

  19. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Get ready for the trip of a lifetime! Royal Kahana 106 is a fantastic unit with tons of space and amazing ocean views! Equipped with cable, wifi, washer/dryer and more. You'll have all the comforts of home! Be sure to take full advantage of the...

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $498/night

  20. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Wonderful ocean views from this spacious penthouse level studio. The owners have completed a beautiful remodel featuring tile floors and a new sofa-sleeper. The full kitchen was recently re-done with new appliances, granite counter tops, new...

    Pool Hot Tub
    FREE CANCELLATION

    $185 to $636/night

  21. CONDOMINIUM
    Pohailani #223

    Pohailani #223

    Lahaina, HI

    Guests are sure to enjoy a memorable family vacation in this fully furnished, 2 bedroom/1 bath condo. The main bedroom has a queen sized bed, while the other bedroom is furnished with 2 Twins. It is perfect for a family as it can sleep 4 people....

    Pool
    FREE CANCELLATION

    $183 to $353/night

  22. CONDOMINIUM
    Kaleialoha #109

    Kaleialoha #109

    Lahaina, HI

    Kaleialoha #109 This DIRECT oceanfront unit has Queen bed and is fully equipped with all basic amenities. AC in living area! New 55" flat screen in living room and 2nd TV in bedroom. Open and airy living area and open kitchen with recent upgrades...

    Pool
    FREE CANCELLATION

    $183 to $336/night

  23. CONDOMINIUM
    Kaleialoha 210

    Kaleialoha 210

    Lahaina, HI

    Imagine yourself staying at this incredible 1 bedroom Ocean Front Condo!! Views of the gorgeous Pacific Ocean and the neighboring islands from your lanai. Watch sea turtles eat seaweed off of the coral right below the lanai as well as watch...

    Pool
    FREE CANCELLATION

    $173 to $616/night

  24. CONDOMINIUM
    Kihei Alii Kai A101

    Kihei Alii Kai A101

    Kihei, HI

    This spacious 2 bedroom, 2 bathroom condo is fully furnished with WiFi, Cable, and A/C in the living area and master bedroom! There are also ceiling fans and floor fans throughout to help keep everything cool in the hot summer months. This unit...

    Pool Hot Tub
    FREE CANCELLATION

    $165 to $610/night

  25. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    SUMMER Special Prices! Ocean front studio with ocean views and central A/C to enjoy those hot summer days. Ready for an unforgettable vacation to Maui? Or is it time to just getaway for the weekend? This studio with a beautiful ocean view is the...

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $373/night

  26. CONDOMINIUM
    Island Sands 210

    Island Sands 210

    Wailuku, HI

    IS 210-SUMMER Special Prices! Tranquil Oceanfront 1-Bedroom, 1-Bathroom Condo in Maalaea: Maui's Best Kept Secret! We invite you to be our guest in our 1-bedroom, 1-bath oceanfront home. There is an air conditioner in the living room to keep...

    Pool
    FREE CANCELLATION

    $160 to $366/night

  27. CONDOMINIUM
    Kamaole Sands 5-313

    Kamaole Sands 5-313

    Kihei, HI

    Ocean and garden views close to the pool. Enjoy beautiful sunsets every evening from your private lanai in this beautifully updated third floor unit! This one bedroom (plus sleeper sofa), two bath, 818 square foot condo is ideal for families or for...

    Pool Hot Tub
    FREE CANCELLATION

    $160 to $563/night

  28. CONDOMINIUM
    Hale Kamaole 109

    Hale Kamaole 109

    Kihei, HI

    Hale Kamaole is the perfect getaway location for couples or small families! Situated in South Kihei near shopping restaurants, and beautiful beaches, you'll have plenty of options to fully experience Maui. This is a spacious 1 bedroom/ 1 bathroom...

    Pool
    FREE CANCELLATION

    $158 to $545/night

  29. CONDOMINIUM
    Kihei Akahi C-616

    Kihei Akahi C-616

    Kihei, HI

    Imagine yourself sitting on the lanai with a drink in hand, watching the gorgeous colors of the Hawaiian sunset! This is a perfect budget getaway. Come explore the island! See gorgeous beaches, taste the island cuisine, shop the local businesses and...

    Pool
    FREE CANCELLATION

    $154 to $543/night

  30. CONDOMINIUM
    Kihei Alii Kai A207

    Kihei Alii Kai A207

    Kihei, HI

    Brand New Renovation! This spacious 1-bedroom, 1 bathroom condo is fully furnished and offers AC, wifi, cable, Dvd player, hairdryer, an in-unit washer and dryer, iron/ironing board, and so much more! You'll also get to enjoy the brand new sofabed...

    Pool Hot Tub
    FREE CANCELLATION

    $154 to $543/night