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
     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Kaunakakai, HI

    You will feel so comfortable and "at home" in the condo that you will be reluctant to leave, but there are other wonderful experiences awaiting you on the grounds of Wavecrest. Wander through the lush tropical grounds, enjoy the fabulous pool right...

    Pool
    FREE CANCELLATION

    $158 to $191/night

  2. 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

  3. CONDOMINIUM
    HiiLani-204

    HiiLani-204

    Lahaina, HI

    Book today and Fall in LOVE with "HiiLani" (In the arms of Heaven)... You will feel like you have gone back in time to the true Hawaiian experience in this condo just 15 FT from the water's edge! 204 Pohailani Welcomes you with so much ALOHA.....

    Pool
    FREE CANCELLATION

    $199 to $264/night

  4. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    Book today and Fall in LOVE with "THE LIL GRASS SHACK" You will feel like you have gone back in time to the true Hawaiian experience in this condo, just 10 FT from the water's edge! 103 Pohailani Welcomes you with so much Included in our fabulous...

    Pool
    FREE CANCELLATION

    $199 to $235/night

  5. CONDOMINIUM
    Aloha Surf 504

    Aloha Surf 504

    Honolulu, HI

    Immerse yourself in the Hawaiian Lifestyle. The boutique-style accommodation is located on the quiet side of the building with free wifi property wide, pool and just three blocks from the beach!    Beautifully decorated and well maintained studio...

    Pool
    FREE CANCELLATION

    $107 to $208/night

  6. CONDOMINIUM
    Aloha Surf Condominium 1412

    Aloha Surf Condominium 1412

    Honolulu, HI

    Immerse yourself in the Hawaiian Lifestyle. The boutique-style accommodation features views from the mountains to the ocean! Free wifi, pool, fitness center and just three blocks from the beach. Within our clean private unit, guests will enjoy: •...

    Pool
    FREE CANCELLATION

    $100 to $197/night

  7. CONDOMINIUM
    Kuhio Village Condominium 1008A

    Kuhio Village Condominium 1008A

    Honolulu, HI

    Private Studio just steps from the world's famous Waikiki Beach. Queen bed, kitchenette, 2 private balconies, free WIFI and cool island breezes. It's all here at a GREAT price!! Within our clean private unit, our guests will enjoy: • Queen bed to...

    FREE CANCELLATION

    $107 to $208/night

  8. CONDOMINIUM
    Hololani A701

    Hololani A701

    Lahaina, HI

    Come and enjoy your Maui vacation at this beautiful 2 bedroom condo at the Hololani Oceanfront resort in wonderful West Maui! Bright blue is all you see as you enter this wonderful space! There is a perfect view of Maui’s majestic sister island...

    Pool
    FREE CANCELLATION

    $261 to $500/night

  9. 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

  10. 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

    $370 to $1,205/night

  11. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    Ready for an unforgettable vacation to Maui? This newly remodeled studio with a beautiful ocean view is the perfect choice! It comes fully furnished with air conditioning, a California King bed, a Twin sofa sleeper, and dining areas both inside and...

    Pool
    FREE CANCELLATION

    $136 to $549/night

  12. CONDOMINIUM
    Honua Kai Konea 642

    Honua Kai Konea 642

    Kaanapali, HI

    JUST RENOVATED AND GORGEOUS! All new hard surface flooring throughout and new living room furnishings! Lounge on the new sofa chaise and watch the waves crash while you enjoy a glass of your favorite wine or a great Hawaiian Kai Tai! Dine at the...

    Pool Hot Tub

    $454 to $1,537/night

  13. CONDOMINIUM
    The Montage Kapalua Bay Heliconia 2302

    The Montage Kapalua Bay Heliconia 2302

    Kapalua, HI

    Beautiful 3 bedroom/3.5 bath plus Den Residence. Heliconia Residence at Residences at Montage This 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...

    Pool

    $1,068 to $5,428/night

  14. CONDOMINIUM
    Honua Kai Konea 312

    Honua Kai Konea 312

    Kaanapali, HI

    UPGRADED 2 PLUS ONE!!! Two Bedroom One Bath! West Maui Mountain & Waterfall Views! 915 sq ft! Just renovated with new DESIGNER FURNISHINGS, new flooring and a brand new Queen Bed in the Private Den! New Flat screen 4K TV's with built in Netflix,...

    Pool Hot Tub

    $352 to $1,211/night

  15. CONDOMINIUM
    Honua Kai Konea 1026

    Honua Kai Konea 1026

    Lahaina, HI

    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 work days during construction hours from 8am to 5pm. This beautiful...

    Pool Hot Tub

    $364 to $1,346/night

  16. 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 $1,624/night

  17. CONDOMINIUM
    Kuhio Village Condominium 809A

    Kuhio Village Condominium 809A

    Honolulu, HI

    Awesome unit with some ocean views, two short blocks from the beach. This unit is a corner unit and has 2 balconies from which you are able to enjoy some ocean views and tropical breezes. Within our clean private unit, our guests will enjoy: •...

    FREE CANCELLATION

    $113 to $214/night

  18. CONDOMINIUM
    Noelani # 115

    Noelani # 115

    Lahaina, HI

    Not one, but two oceanfront pools and a Jacuzzi, what more can you ask for? Unit 115 is a ground floor unit with washer and dryer and air conditioning. You'll love just walking out from your private lanai right into the swimming pool. Turtles play...

    Pool
    FREE CANCELLATION

    $228 to $313/night

  19. CONDOMINIUM
    Aina Nalu Premier E102 Last Minute Special

    Aina Nalu Premier E102 Last Minute Special

    Lahaina, HI

    Enveloped by serene gardens and detailed with stylish Asian-inspired decor, your 1BR condo combines all the comforts of home with the luxe amenities of a boutique resort. As part of the small, exclusive community at Aina Nalu, you’ll enjoy access...

    Pool Hot Tub
    FREE CANCELLATION

    $154 to $480/night

  20. HOUSE
    Aniani Hale

    Aniani Hale

    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

  21. CONDOMINIUM
    Kuleana 622 1Bdrm

    Kuleana 622 1Bdrm

    Lahaina, HI

    Relax in paradise at our beautiful one bedroom, one bathroom oceanfront condo at the Kuleana Resort!  Enjoy spectacular sunsets and whale watching (during the winter months) from the privacy of your living room or lanai.  Our 3rd floor suite...

    Pool
    FREE CANCELLATION

    $225 to $448/night

  22. CONDOMINIUM
    Honua Kai Hokulani 841

    Honua Kai Hokulani 841

    Kaanapali, HI

    This large two bedroom/two bath condo in the hokulani interior courtyard is the perfect vacation spot. With 1320 sq ft of interior living space and an over sized 340 sq ft wraparound lanai, HOKULANI 841 is one of the largest two bedroom condos at...

    Pool Hot Tub

    $519 to $1,929/night

  23. CONDOMINIUM
    Maui Eldorado I204/205

    Maui Eldorado I204/205

    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
    FREE CANCELLATION

    $383 to $551/night

  24. CONDOMINIUM
    Kaanapali Shores 259

    Kaanapali Shores 259

    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

    $321 to $1,168/night

  25. 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

  26. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Ko Olina Kai is a peaceful gated community that offers all the tranquil privacy you could desire! The interior is spacious and homey with 2 bedrooms, 2 baths, a living room with an adjacent dining space, and a kitchen. This outstanding villa offers...

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $158/night

  27. 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

  28. TOWNHOUSE
    1085E Ko Olina Kai Townhome

    1085E Ko Olina Kai Townhome

    Kapolei, HI

    Lovely, developer upgraded unit overlooking the greenbelt close to the tropical pool area. You will feel like you are truly in paradise, when you relax in this tropical home. The home features rich wood cabinets, granite counters, all stainless...

    Pool Hot Tub

    $218/night

  29. CONDOMINIUM
    Leinaala Oceanfront #302

    Leinaala Oceanfront #302

    Kihei, HI

    Leinaala is a small 24 unit oceanfront property with panoramic views. Each unit faces the ocean. Leinaala has a relaxed and private atmosphere with a great feeling of the aloha spirit. There is an oceanfront pool, gas barbecue for your use, and...

    Pool
    FREE CANCELLATION

    $161 to $278/night

  30. CONDOMINIUM
    Ilikai Marina Condo 1290

    Ilikai Marina Condo 1290

    Honolulu, HI

    If you are looking for a fully equipped unit with 180 degree of ocean and beautiful Hawaiian scenery, then your search is over and you have found your home away from home in paradise. The location cant be beat and the peaceful ambiance and tranquil...

    FREE CANCELLATION

    $168 to $309/night