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
    Wailea Elua #2204

    Wailea Elua #2204

    Wailea, Maui, HI

    You will immediately sense that the fabulous Maui vacation you have been looking forward to has begun when you step into this completely remodeled 2 bedroom, 2 bath condo located on one of the best locations in the Wailea Elua Village. From our...

    Pool

    $724 to $1,065/night

  2. CONDOMINIUM
    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai

    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai...

    Kailua Kona, HI

    An upstairs residence at Four Seasons Resort Hualalai, 2901B offers the ultimate in Big Island luxury. With amazing ocean and sunset views, central air conditioning, stylish décor, and use of a golf cart included in every rental, this villa...

    Pool

    $720 to $2,118/night

  3. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Island living at its finest! Experience charming plantation style living in this gorgeous South Shore home. Enjoy all the Robert Trent Jones, Jr. community has to offer conveniently located along the Kiahuna Golf Course. Shopping, golf, and beach...

    Pool Hot Tub

    $702 to $1,910/night

  4. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Hale Ili Ili is an oceanfront gated 4 plex.This property is steps from Kamaole Beach #1 and Charley Young's Cove. Panoramic ocean views and magnificent sunsets can be seen daily from this property. This property has an oceanfront pool, hot tub and...

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/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

    $695 to $1,759/night

  6. HOUSE
    Lokelani

    Lokelani

    Hanalei, HI

    LOKELANI - (Heavenly Rose) TVNC-1226 TA189-999-3088-01 A luxury beach house close to Hanalei town and the beautiful Bay. This tastefully decorated three bedroom, three bath home is truly a little slice of heaven. From the moment you enter the...

    $689 to $919/night

  7. CONDOMINIUM
    Makena Surf Resort #E-205

    Makena Surf Resort #E-205

    Kihei, HI

    A Note from The Owners: Our dream-come-true was to have a unit directly overlooking the beach at Makena. We can literally talk to each other from the lanai to the beach! We did a remodel which, among other features, allows us to push all the glass...

    Pool

    $687 to $1,319/night

  8. HOUSE
    Hale Lokahi

    Hale Lokahi

    Waialua, HI

    Hale Lokahi - House of Peace and Serenity - This home is located in one of the best kept, secret neighborhoods on the north shore. Right on a white sand beach, this family-owned house is perfect for your vacation in paradise.. This 4 bedroom, 2...

    $683 to $992/night

  9. CONDOMINIUM
    B-110: Hale Papakea Ko Olina Beach Villa

    B-110: Hale Papakea Ko Olina Beach Villa

    Kapolei, HI

    One of only two ground floor beachfront 2 bedroom 2 bathroom condos that are closer to the beach than any other Ko'Olina Resort residence. Experience the ultimate oceanfront experience with family and friends. We manage both beachfront units, which...

    Pool Hot Tub

    $682 to $2,016/night

  10. CONDOMINIUM
    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    Kapolei, HI

    The Hale Nani Ikena Kai beach villa at Ko Olina offers exactly what its name suggests; a home with a “Beautiful Ocean View”. Spectacular direct whitewater ocean and beach views will be what greets you at this upscale, luxurious ground floor...

    Pool Hot Tub

    $682 to $2,016/night

  11. CONDOMINIUM
    Ko Olina Beach Villa (O121)

    Ko Olina Beach Villa (O121)

    Kapolei, HI

    Celebrities want privacy and quick exit routes, but so does everyone else! You deserve this one-of-a-kind Ko Olina Beach Villa, unlike any other located within the resort. It boasts over 1600 sq.ft of living space, 3 ground floor private lanais, no...

    Pool Hot Tub

    $682 to $1,668/night

  12. VILLA
    Bay Villa 21G4 GOLD Beach Front

    Bay Villa 21G4 GOLD Beach Front

    Kapalua, HI

    The name 'Kapa' 'lua' means above waters edge. This ocean front beauty is uniquely perched above the waters edge along the most desirable stretch of Maui coastline just steps from the sand. Quiet coves make for excellent snorkeling and swimming,...

    Pool

    $678 to $915/night

  13. VILLA
    Bay Villa 20B3 Gold Beach Front

    Bay Villa 20B3 Gold Beach Front

    Kapalua, HI

    This stunning designer renovation is on the most desirable beach front property in Kapalua. It is just steps away from the white sands below and boardwalk connecting to the resort’s three mile coastal trail. Wrap yourself in the luxury of our...

    Pool

    $678 to $915/night

  14. CONDOMINIUM
    Ocean and Pool View Beachfront 2nd Floor Villa 208

    Ocean and Pool View Beachfront 2nd Floor Villa 208

    Kahuku, HI

    This villa is located on the second level with Spectacular Ocean and pool views from the lanai, the living room, the dining room, and the master bedroom! This villa is just 35 yards from the sandy beach and 10 yards to the Pool and BBQs. It has...

    Pool Hot Tub

    $677 to $2,217/night

  15. CONDOMINIUM
    Direct Ocean View Beach Level 3Bed Villa 103

    Direct Ocean View Beach Level 3Bed Villa 103

    Kahuku, HI

    Direct Ocean View Beach Level 3Bed (or 4Bed w/Adjoin Studio) Villa 103 This villa is in the most desirable location in the complex. It has just 20 yards of lawn before the sandy beach and the pool and BBQs are just 50 yards to the right!  It has...

    Pool Hot Tub

    $677 to $2,609/night

  16. CONDOMINIUM
    Ocean & Pool View Beachfront 3rd Floor Penthouse Villa 309

    Ocean & Pool View Beachfront 3rd Floor Penthouse Vil...

    Kahuku, HI

    Ocean & Pool View Beachfront 3rd Floor (top) Penthouse Villa 309 This penthouse villa is located on the third level just steps from the sandy beach with beautiful ocean and pool views from the lanai, living room and master bedroom. It has a serene...

    Pool Hot Tub

    $651 to $2,217/night

  17. CONDOMINIUM
    Ocean View and Beachfront Beach Level 3 Bedroom Villa 110

    Ocean View and Beachfront Beach Level 3 Bedroom Villa 11...

    Kahuku, HI

    This beach level villa is located just steps from the pool, BBQs, and the sandy beach! It has partial ocean views from the dining room, kitchen, living room, master bedroom and lanai. It has a serene lanai with Tiki torches lighting the grounds at...

    Pool Hot Tub

    $651 to $2,217/night

  18. 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

  19. CONDOMINIUM
    Honua Kai Konea 301

    Honua Kai Konea 301

    Kaanapali, HI

    One of the MOST DESIRABLE 2 bedroom 2.5 bath condo in the entire complex. Konea 301 is one 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...

    Pool Hot Tub
    FREE CANCELLATION

    $645 to $2,287/night

  20. CONDOMINIUM
    Whaler at Kaanapali Beach 912

    Whaler at Kaanapali Beach 912

    Lahaina, HI

    Completely Remodeled and well-appointed one (1) bedroom, two (2) bath condo. Custom cabinetry, granite counter tops, built-in wine cooler and stainless steel appliances greet you as you walk in. Quality furnishings inspire luxury in this...

    Pool Hot Tub
    FREE CANCELLATION

    $634 to $824/night

  21. 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
    FREE CANCELLATION

    $631 to $2,167/night

  22. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    Hale Ola Kai is a three bedroom, two and a half bath home located near world famous Hanalei Bay. The house is a comfortable family-style home. Casual, yet equipped with anything you need to make your stay in Hanalei perfect. Two of the bedrooms have...

    $613 to $842/night

  23. VILLA
    Bay Villa 22G4 Gold Ocean Front

    Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Dreaming of Paradise? You'll pinch yourself when you walk into this gorgeous Bay Villa. It's everything you imagined and more, including discounts on tee times at the world-famous Plantation and Bay Courses. Start your vacation with a frosty...

    Pool

    $610 to $847/night

  24. VILLA
    Bay Villa 36B3 Gold Ocean Front

    Bay Villa 36B3 Gold Ocean Front

    Kapalua, HI

    This elegant and upscale villa occupies the top two floors and features rare West-facing views for magnificent sunsets! A whale watchers dream! This villa offers the best vantage of whales and their young who make the bay their playground during...

    Pool

    $610 to $847/night

  25. VILLA
    Bay Villa 17B2 Gold Ocean View

    Bay Villa 17B2 Gold Ocean View

    Kapalua, HI

    Over $600K in recent upgrades! Even the best photos can not capture the true beauty of the high-end materials used, the designer furniture and accessories and the magnificent views that surround this 5 star property. If you have ever dreamed of...

    Pool

    $610 to $1,152/night

  26. VILLA
    Kapalua Bay Villa 29B2

    Kapalua Bay Villa 29B2

    Lahaina, HI

    Kapalua Bay Villa at its best! This oceanfront property was built to enjoy the casual lifestyle of Kapalua. Beautiful views and the sound of the blue pacific greet you from every part of this unbelievable property. This spacious two bedroom, three...

    Pool

    $610 to $1,118/night

  27. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Wailea Elua is the premier ocean front property in Wailea. A gated property situated right on picturesque 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...

    Pool Hot Tub
    FREE CANCELLATION

    $609 to $1,073/night

  28. HOUSE
    Alii Point- Almost Oceanfront

    Alii Point- Almost Oceanfront

    Kailua Kona, HI

    Almost Oceanfront. Spend your vacation in a luxurious single family home within a private, gated, enclave of 16 seaside homes. This Alii Point subdivision of fine, luxury residences is a tropical paradise surrounded by a botanical garden with beach...

    Pool

    $608 to $791/night

  29. CONDOMINIUM
    Honua Kai Hokulani 509

    Honua Kai Hokulani 509

    Kaanapali, HI

    Hokulani #509 is located in one of the most desirable stacks on the entire property. Forward facing interior corner view location for catching the whales or just watching the SUNSET. This fabulous 2 bedroom/2 bath upgraded condo is in the Hokulani...

    Pool Hot Tub
    FREE CANCELLATION

    $607 to $1,871/night

  30. 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
    FREE CANCELLATION

    $607 to $1,973/night