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
    Oceanfront Nohonani- Unforgettable Views

    Oceanfront Nohonani- Unforgettable Views

    Lahaina, HI

    This recently updated 2BR/2BA oceanfront condo at Nohonani offers incredible views of both Lanai and Molokai from its fourth-floor perch. Sip drinks on the private lanai while taking in the sunset over the Pacific. Enjoy resort-style amenities,...

    Pool
    FREE CANCELLATION

    $158 to $561/night

  2. CONDOMINIUM
    Ilikai 815

    Ilikai 815

    Waikiki, HI

    MOUNTAIN & CITY VIEWS. STEPS TO WAIKIKI BEACH. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life. The iconic Ilikai Suites are located at the gateway to Waikiki. This condo is a fully equipped...

    Pool
    FREE CANCELLATION

    $132 to $250/night

  3. CONDOMINIUM
    Ilikai 1308

    Ilikai 1308

    Waikiki, HI

    STUNNING OCEAN / SUNSET / MARINA VIEWS! STEPS TO WAIKIKI BEACH. Memorable Meals from the Lanai. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life. Beautiful high end recent remodel. Fully...

    Pool
    FREE CANCELLATION

    $138 to $262/night

  4. CONDOMINIUM
    Ilikai 908

    Ilikai 908

    Waikiki, HI

    STUNNING OCEAN & SUNSET VIEWS! STEPS TO WAIKIKI BEACH. Memorable Meals from the Lanai. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life. The iconic Ilikai Resort is located at the gateway to...

    Pool
    FREE CANCELLATION

    $132 to $262/night

  5. CONDOMINIUM
    Maui Eldorado Condo D100

    Maui Eldorado Condo D100

    Kaanapali, HI

    New to our Eldorado vacation rental pool, enjoy this spacious 2 Bedroom 2 full bathroom in the Kaanapali beach resort area. Short walk to Whaler's Village shops, restaurants and Kaanapali beach. Enjoy the Resort's exclusive beachfront clubhouse...

    Pool
    FREE CANCELLATION

    $345 to $753/night

  6. HOUSE
    Hanalei Bay Villa 26

    Hanalei Bay Villa 26

    Princeville, HI

    Hanalei Bay Villa 26 is one of our most popular Kauai vacation rentals with it's great views, short walk to beach, and updated charming interior. It's an easy walk to Hideaways Beach (across the street) or St Regis Beach (about the equivalent of a...

    FREE CANCELLATION

    $229 to $336/night

  7. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    One of West Maui's most exclusive legally permitted rental properties, the Makena Aloha Estate offers exceptional ocean and mountain views, with gated exclusive privacy and seclusion. With 4,400 square feet of interior dwelling space, this...

    Pool

    $1,968 to $3,075/night

  8. CONDOMINIUM
    Kuleana 713 1 Bdrm

    Kuleana 713 1 Bdrm

    Lahaina, HI

    Relax and enjoy the beautiful Pacific Ocean and stunning West Maui sunsets from your living room and private lanai! Find yourself staring at the hues of ocean blues and lush colors of the plants, flowers and trees.  Watch the turtles swim up to the...

    Pool
    FREE CANCELLATION

    $230 to $346/night

  9. CONDOMINIUM
    Hale Kamaole #236

    Hale Kamaole #236

    Kihei, HI

    Begin your day with the golden sunlight of the Valley Isle emerging over Haleakala and bringing the multicolored hues of Maui to life. Whether you’re in Hawaii for an action-packed island vacation or a relaxing retreat to the Paradise in the...

    Pool
    FREE CANCELLATION

    $196 to $309/night

  10. 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

  11. CONDOMINIUM
    Hale Kamaole #174

    Hale Kamaole #174

    Kihei, HI

    This Ideal, Maui Vacation Rental unit #174, has it all. The owners of this condo prefer only 2 adults. Ocean & garden view garden. Completely remodeled from top to bottom in 2017. Bedroom features New King bed, 2 night stands and standing. Bedroom...

    Pool
    FREE CANCELLATION

    $196 to $318/night

  12. CONDOMINIUM
    Sea Shells Turtle Bay Condo

    Sea Shells Turtle Bay Condo

    Kahuku, HI

    Ground Floor Unit. Nice remodeled unit with Hawaiian decor. Air conditioning in the bedroom. Lanai with table and 2 chairs. California king bed . 42" flat screen TV. WIFI. Remodeled bathroom with tiled shower Welcome to Kuilima Estates, the condo...

    Pool
    FREE CANCELLATION

    $179 to $210/night

  13. 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

  14. HOUSE
    Kahana Sunset B3B

    Kahana Sunset B3B

    kahana, HI

    Beautiful ocean view one bed one bath condo located at Kahana Sunset Resort on Keonenui Bay just south of Napili and Kapalua. Great ocean views of the islands of Molokai and Lanai from the beach area. Short walk from this unit to the ocean, pool and...

    Pool

    $186 to $214/night

  15. CONDOMINIUM
    Pacific Shores #A-101

    Pacific Shores #A-101

    Kihei, HI

    Located in in the heart of South Kihei, the Pacific Shores complex is central to the best activities South Maui has to offer. Just a quick stroll in any direction will take you to nearby shopping, popular restaurants, and world famous beaches. Take...

    Pool Hot Tub
    FREE CANCELLATION

    $153 to $244/night

  16. CONDOMINIUM
    Makahuena 2202

    Makahuena 2202

    Koloa, HI

    The Poipu vacation rentals at Makahuena Point are located in the most southern point on the island, from which you can watch both the sunrise and sunset. Makahuena Point has crashing waves and beautiful splashing surf, with only a short walk to...

    Pool Hot Tub
    FREE CANCELLATION

    $216 to $856/night

  17. HOUSE
    Leilani Hale

    Leilani Hale

    Kailua Kona, HI

    Tucked into the side of the mountain just above Kona at a cooler 600 ft. elevation Happy Leilani Hale has a zen feel to it as you look out over the blue pacific and feel the Soft ocean breezes take you away from it all. Enter through the Asian...

    Pool

    $425 to $729/night

  18. CONDOMINIUM
    Kamaole Sands #03-105

    Kamaole Sands #03-105

    Kihei, HI

    Don’t just visit Maui, Experience Maui. Maui is a place of adventure, discovery, and wonder and most travelers today want to experience a destination as a local, not as a tourist. They want to blend in, shop at local markets, eat new foods and...

    Pool
    FREE CANCELLATION
  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
    Ko Olina Beach Villa O701

    Ko Olina Beach Villa O701

    Kapolei, HI

    LOCATION: This Villa is located on the 7th floor of the Ocean Tower at the Beach Villas at Ko Olina right on Lagoon 2. Leave the world behind as you’re greeted by the warm blue expansive ocean views from the living area and spacious lanai...

    Pool

    $369 to $1,204/night

  21. CONDOMINIUM
    Hale Lani (1-Bedroom Condo)

    Hale Lani (1-Bedroom Condo)

    Kahuku, HI

    Welcome to Kuilima Estates, the condo property located on the grounds of world-renowned Turtle Bay. The condos are surrounded by two beautifully manicured golf courses, and are the only condos on the North Shore. This is a great place to relax,...

    Pool
    FREE CANCELLATION

    $256 to $299/night

  22. CONDOMINIUM
    Mahana 701

    Mahana 701

    Lahaina, HI

    Beautiful 7th floor 2br/2ba condominium at The Mahana at Kaanapali provides everything you need for your vacation in paradise. Equipped with granite counter tops, beautiful tile floors, central A/C, WiFi, flat screen TV, stocked kitchen, and...

    Pool
    FREE CANCELLATION

    $516 to $1,665/night

  23. CONDOMINIUM
    Pikake Kahuku Turtle Bay Condo

    Pikake Kahuku Turtle Bay Condo

    Kahuku, HI

    Comfortable two bedroom with loft, two bath condo. Accommodates 5. WIFI. No land line Welcome to Kuilima Estates, the condo property located on the grounds of world-renowned Turtle Bay. The condos are surrounded by two beautifully manicured golf...

    Pool
    FREE CANCELLATION

    $241 to $266/night

  24. CONDOMINIUM
    Alii Kai II 8H

    Alii Kai II 8H

    Princeville, HI

    Our vacation rentals at Aliii Kai II are part of a quiet, intimate complex with pool, jacuzzi, and barbecue area. Shopping, dining, and the charming town of Hanalei are just minutes away. Alii Kai 8H is a spacious two bedroom, two bath condo that...

    Pool Hot Tub
    FREE CANCELLATION

    $182 to $257/night

  25. HOUSE
    Ainamalu Home 69-9242

    Ainamalu Home 69-9242

    Waikoloa Village, HI

    Come and enjoy a luxurious laid-back island living in our new home located in the beautiful new neighborhood in Waikoloa Beach Resort – Ainamalu. This gated community Ainamalu is the newest resort community in the beautiful Waikoloa Beach Resort,...

    FREE CANCELLATION

    $649 to $896/night

  26. APARTMENT
    MS608 THTH-CTOQ(MA)-00-ACH

    MS608 THTH-CTOQ(MA)-00-ACH

    Honolulu, HI

    Studio great for solo travelers or families with kids. Two double beds in the unit, kitchenette, and full bath. Vanity next to bathroom or use the space as a work space. Includes Free Parking Stall! Don't lose vacation time trying to find parking in...

    Pool
    FREE CANCELLATION

    $144 to $181/night

  27. CONDOMINIUM
    Royal Mauian Unit #516

    Royal Mauian Unit #516

    Kihei, HI

    Royal Mauian is a unique six story oceanfront property located in South Kihei offering unobstructed views of the clear blue Pacific. The property and adjacent Kamaole Beach together provide excellent locations for stunning sunsets, snorkeling,...

    Pool

    $324 to $505/night

  28. CONDOMINIUM
    Kihei Surfside, #612

    Kihei Surfside, #612

    Kihei, HI

    Kihei Surfside Resort is a unique six story oceanfront property located in South Kihei offering 180-degree views of the clear blue Pacific. The property and adjacent Keawekapu Beach together provide excellent locations for stunning sunsets,...

    Pool

    $178 to $427/night

  29. DUPLEX
    Terrace Duplex Unit #A

    Terrace Duplex Unit #A

    Honolulu, HI

    All photos, amenities, calendar, and rates are 100% accurate. We will notify you proactively when early check-in / late check-outs are possible and you'll receive the comforts of home with a starter supply of shampoo, soaps, paper products and...

    Hot Tub Pets OK
    FREE CANCELLATION

    $493 to $744/night

  30. CONDOMINIUM
    Honu Lani Turtle Bay Condo

    Honu Lani Turtle Bay Condo

    Kahuku, HI

    Lovely ground floor condo with many extras, including WIFI, and a beautiful 32" HDTV in the living room. VCR and DVD. For extra comfort, there are 2 a/c units, one in the bedroom, and one in the living room. Welcome to Kuilima Estates, the condo...

    Pool
    FREE CANCELLATION

    $214 to $261/night