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, #1601*

    WAILEA ELUA, #1601*

    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

    $471 to $896/night

  2. TOWNHOUSE
    Pili Mai 11I

    Pili Mai 11I

    Koloa, HI

    Enjoy modern Hawaii living at Pili Mai 11I Pack your golf clubs and get ready to enjoy modern Hawaii living in this exclusive Poipu community. Located on the 9th hole of the beautiful Kiahuna Golf Course, this exceptionally beautiful,...

    Pool Hot Tub

    $470 to $1,150/night

  3. CONDOMINIUM
    Grand Champions 089

    Grand Champions 089

    Wailea, HI

    Remodeled two bedroom condo at Wailea Grand Champions with fabulous views of the golf course. This condo completed renovations in November 2016 and features a completely renovated Kitchen and bathrooms and new furnishings. The Kitchen has new...

    Pool Hot Tub
    FREE CANCELLATION

    $469 to $688/night

  4. 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

    $466 to $1,887/night

  5. CONDOMINIUM
    Wailea Elua #102

    Wailea Elua #102

    Kihei, 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

    $464 to $696/night

  6. CONDOMINIUM
    Wailea Elua #207

    Wailea Elua #207

    Kihei, 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
    FREE CANCELLATION

    $464 to $725/night

  7. CONDOMINIUM
    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

    $464 to $1,467/night

  8. HOUSE
    Iki Nui Hale

    Iki Nui Hale

    Princeville, HI

    This home is a short walking distance to Queen's Bath as well as Hideaways Beach! For all you golf enthusiasts, Makai Golf Course is a short walk from this home as well! The Princeville Public Library, Princeville Park as well as the shopping center...

    $464 to $951/night

  9. VILLA
    Poolside Bungalow 3bed/3bath, w/ Pool & Hot Tub- Steps To Beach

    Poolside Bungalow 3bed/3bath, w/ Pool & Hot Tub- Ste...

    Kihei, HI

    Poolside Bungalow is a three bedroom, 3 bath two-level condominium suite. Two bedrooms each have a full bathroom and are located on the ground floor. The third bedroom is located below ground level, down a spiral staircase from the living room. The...

    Pool

    $463 to $984/night

  10. CONDOMINIUM
    Keauhou Surf & Racquet Townhouse #36

    Keauhou Surf & Racquet Townhouse #36

    Kailua Kona, HI

    Townhouse living at it's finest. 3 bedroom property at an amazing value. sleeps 8. New appliances, furniture, granite counter tops; TV in the living room & in all the bedrooms. There are 2 queen beds upstairs with a window A/C unit in the...

    Pool
    FREE CANCELLATION
  11. CONDOMINIUM
    Wailea Elua Unit #0307

    Wailea Elua Unit #0307

    Wailea, HI

    A note from the owner: Welcome to Wailea Elua Village #307, our newly remodeled ground floor condo and our piece of paradise. With outstanding views, beach access through beautifully sculpted gardens, and Hawaiian-home class, it has everything you...

    Pool Hot Tub

    $459 to $953/night

  12. CONDOMINIUM
    Wailea Elua Unit #1503

    Wailea Elua Unit #1503

    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

    $459 to $953/night

  13. CONDOMINIUM
    Waterfall House

    Waterfall House

    Kailua-Kona, HI

    Beautiful high end home with views directly to the ocean below. Have your own private retreat within a secure, gated community in an expansive open home. Stay in perhaps one of the most unique homes in Hawaii where it rains into the house, filling...

    Pool Hot Tub

    $459 to $1,899/night

  14. CONDOMINIUM
    Wailea Elua Unit #801

    Wailea Elua Unit #801

    Wailea, HI

    Notes from the Owner: Wailea Elua Village #801 is located in the center of the Elua Village just across from the small pool and Jacuzzi area and just steps to the paddle court. Enjoy ocean views as well as secluded garden views from this quiet...

    Pool Hot Tub

    $459 to $953/night

  15. CONDOMINIUM
    Wailea Elua Unit #0802

    Wailea Elua Unit #0802

    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 Hot Tub

    $459 to $953/night

  16. VILLA
    Waipouli Beach Resort A207

    Waipouli Beach Resort A207

    Kapaa, HI

    Your Dream Vacation in Paradise! Royal Beachfront Penthouse Villa an exquisite Ocean Front Villa! Located in Oceanfront A Building, the most desired building at Waipouli Beach Resort on Beautiful Kauai.  Come stay with us for breathtaking views of...

    Pool
    FREE CANCELLATION

    $458 to $834/night

  17. CONDOMINIUM
    Ko Olina Beach Villa (O1105)

    Ko Olina Beach Villa (O1105)

    Kapolei, HI

    This 3BD Penthouse Beach Villa is located on the 11th floor of the Ocean Tower and is 1,734 sq ft of luxury. It features ocean views the kitchen and living/dining area. The master bedroom has a private lanai with views of the golf course and...

    Pool Hot Tub

    $456 to $1,668/night

  18. HOUSE
    Paradise Bluff

    Paradise Bluff

    Laupahoehoe, HI

    *Published rates are for double occupancy. Extra guests up to a total of six are charged $25 per night. All guests must be registered, Mahalo! Paradise Bluff is a beautiful home perched on the cliffs of the small seaside town of Laupahoehoe....

    Pool

    $452 to $979/night

  19. CONDOMINIUM
    Royal Sea Cliff #704

    Royal Sea Cliff #704

    Kailua Kona, HI

    Enjoy upscale penthouse living at this fully furnished ocean front luxury resort condominium complex in Kona. Breathtaking white water views, marble floors, soaring ceilings, spacious tiled lanai with wet bar, upgraded cabinetry and countertops...

    Pool Hot Tub
    FREE CANCELLATION
  20. CONDOMINIUM
    Maui Kamaole i-212

    Maui Kamaole i-212

    Kihei, HI

    Enjoy Ocean Views from this second floor condo featuring two bedrooms and two bathrooms. The master bedroom is located in the loft and has a king bed and a full bathroom ensuite. The second bedroom is located on the main floor and has two (2) twin...

    Pool
    FREE CANCELLATION

    $450 to $575/night

  21. CONDOMINIUM
    Maui Kamaole #C-207

    Maui Kamaole #C-207

    Kihei, HI

    100% renovated Ocean View 2 bedroom Loft condo. The renovation was completed in June 2018! This stunning condo has just been remodeled with top of the line materials and impeccable taste. This is truly a piece of paradise. Located at the popular...

    Pool Hot Tub
    FREE CANCELLATION

    $450 to $575/night

  22. CONDOMINIUM
    Grand Champions #118

    Grand Champions #118

    Wailea, HI

    Spacious two bedroom condo at the Wailea Grand Champions in the heart of Wailea in South Maui. Two spacious bedrooms and a large living area make this condo the perfect Maui getaway. The master bedroom has a king bed and a full bath en-suite. The...

    Pool Hot Tub
    FREE CANCELLATION

    $450 to $572/night

  23. CONDOMINIUM
    Maui Kamaole h-201

    Maui Kamaole h-201

    Kihei, HI

    When you step into this two bedroom condo, the first thing you notice is the completely remodeled kitchen. The shaker style cabinets are a bold statement and accentuate the captivating backsplash. The granite countertop and under mount sink are both...

    Pool
    FREE CANCELLATION

    $450 to $575/night

  24. CONDOMINIUM
    Maui Kamaole c-209

    Maui Kamaole c-209

    Kihei, HI

    Ocean view Condo with two bedroom and two bathrooms. This unit sleeps up to six (6) people with a Queen bed in the master bedroom loft, two twins/King bed in the second bedroom on the main floor and a pull out sofa bed in the living room. Beautiful...

    Pool
    FREE CANCELLATION

    $450 to $575/night

  25. CONDOMINIUM
    Maui Kamaole j-214

    Maui Kamaole j-214

    Kihei, HI

    Enjoy ocean views from this well appointed second floor Condo. This unit features two bedrooms and two full bathrooms. The furnishings are a mixture of modern and tropical. The kitchen features bright white cabinetry and a light gray counter top...

    Pool
    FREE CANCELLATION

    $450 to $575/night

  26. CONDOMINIUM
    Grand Champions 090

    Grand Champions 090

    WAILEA, HI

    Beautifully Remodeled and furnished two bedroom Condo overlooking the Golf Course. The kitchen ad bathrooms have been recently renovated. This unit offers many upgrades throughout and has many new furnishings. The bedrooms have all new furniture and...

    Pool
    FREE CANCELLATION

    $450 to $572/night

  27. CONDOMINIUM
    Makena Surf Resort #F-209

    Makena Surf Resort #F-209

    Kihei, HI

    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and...

    Pool

    $448 to $1,094/night

  28. CONDOMINIUM
    Wailea Elua Unit #0105

    Wailea Elua Unit #0105

    Wailea, HI

    About this condo: Wailea Elua Village #105 is a ground floor, two bedroom-two bath, ocean view condo with a large lanai complete with a sun shade screen. It has a king bed in the master bedroom, twins in the guest bedroom and a sofa sleeper for...

    Pool Hot Tub

    $448 to $953/night

  29. CONDOMINIUM
    Wailea Elua Unit #0902

    Wailea Elua Unit #0902

    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

    $448 to $1,065/night

  30. CONDOMINIUM
    Wailea Elua Unit #0302

    Wailea Elua Unit #0302

    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

    $448 to $823/night