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
    Sands Of Kahana 474

    Sands Of Kahana 474

    Lahaina, HI

    Experience the good life 'Hawaiian style' as you sit on your private lanai watching the sunset and enjoying the balmy trade winds. This striking 3 bedroom, 3 bathroom penthouse has one-of-a kind views of Molokai and Lanai. It is a beautiful, newly...

    Pool Hot Tub

    $473 to $526/night

  2. CONDOMINIUM
    Wailea Elua, #1601

    Wailea Elua, #1601

    Wailea, HI

    About this condo: Wailea Elua Village #1601 is an inviting ground floor one bedroom, two bath oceanfront condo plus sofa sleeper with a large wrap-around lanai: the perfect location for watching stunning Maui sunsets and enjoying the lush tropical...

    Pool Hot Tub

    $471 to $896/night

  3. 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 $1,137/night

  4. 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
    FREE CANCELLATION

    $469 to $1,603/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
    Ohana Hale

    Ohana Hale

    Kihei, HI

    Ohana Hale is a charming two bedroom, two bath ground floor condominium suite. Each bedroom has one full bathroom and its own private entrance to the pool. Each bedroom has your choice of a King bed or 2 Twin beds. They also include two beach...

    Pool Hot Tub

    $463 to $786/night

  7. CONDOMINIUM
    O-212 Ko Olina Beach Villa

    O-212 Ko Olina Beach Villa

    Kapolei, HI

    This 3 bedroom, 3 Bath Luxury Villa on the 2nd floor of the Ocean Tower is conveniently located just 20 miles from Honolulu International Airport on the beautiful southwestern shores of Oahu. The four pristine Ko Olina beaches and lagoons are just...

    Pool Hot Tub

    $462 to $1,500/night

  8. 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

  9. 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

  10. 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

  11. 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

    $459 to $953/night

  12. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Unit 143 at the Wailea Grand Champions is a rare 3 bedroom 2 bath unit with magnificent golf course views. It has been recently renovated with all new furnishings. It has a fully equipped kitchen, washer and dryer, room AC in each room as well as...

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night

  13. CONDOMINIUM
    Wailea Elua #2110

    Wailea Elua #2110

    Wailea, 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
    FREE CANCELLATION

    $458 to $725/night

  14. COTTAGE
    Honl's Beach Hale (Big Island)

    Honl's Beach Hale (Big Island)

    Kailua Kona, HI

    Location, location, location!!! HONLS BEACH HALE is located in the heart of the Kona Coast on the famous Ali'i Dr. This fantastic ocean front property offers unsurpassed, stunning sunset views. Hear the waves crashing and smell the sea spray as...

    Hot Tub

    $452 to $1,038/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
    FREE CANCELLATION

    $452 to $1,436/night

  16. 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

    $450 to $572/night

  17. 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

  18. 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

  19. CONDOMINIUM
    Wailea Elua Unit #2107

    Wailea Elua Unit #2107

    Wailea, HI

    A Note From the Owner: You will love the extra space in this remodeled supersized two-bedroom, two-bath Elua condo. With nearly 300 square feet more than the typical Elua two-bedroom unit, you can spread out, relax and truly enjoy your stay in...

    Pool Hot Tub

    $448 to $897/night

  20. CONDOMINIUM
    Wailea Elua Unit #2106

    Wailea Elua Unit #2106

    Wailea, HI

    Note from the Owner: Nothing Beats Living in Paradise; Catch that Mahalo Feeling. Picture yourself here! And a sigh escapes your lips as you walk through the door. Postcard Perfect 'South Pacific' sunsets await you. Swaying palm trees silhouetted...

    Pool Hot Tub

    $448 to $897/night

  21. CONDOMINIUM
    Wailea Elua, #2003

    Wailea Elua, #2003

    Wailea, HI

    A note from the owner: You will love the elegance of this remodeled one-bedroom, two-bath Elua condo. You can spread out, relax and truly enjoy your stay in paradise. Our large lanai, living room and master bedroom are ocean facing, with a...

    Pool Hot Tub

    $448 to $823/night

  22. CONDOMINIUM
    Whaler at Kaanapali Beach 514

    Whaler at Kaanapali Beach 514

    Lahaina, HI

    Completely Renovated and well-appointed Studio, Ocean view condo. Attention to detail and fine finishes make this condo a great choice. Wake up to ocean views from the comfort of your king bed or enjoy your morning coffee on the lanai over-looking...

    Pool Hot Tub
    FREE CANCELLATION

    $444 to $639/night

  23. 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

    $437 to $1,717/night

  24. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    The Sugar Beach Resort is the perfect destination for your tropical Hawaiian getaway! This oceanfront complex is just a few steps away from Maui's longest continual white sand beach, perfect for long strolls on the beach or enjoying postcard...

    Pool Hot Tub
    FREE CANCELLATION

    $428 to $579/night

  25. CONDOMINIUM
    B-305: Hale Moana Ko Olina Beach Villa

    B-305: Hale Moana Ko Olina Beach Villa

    Kapolei, HI

    Located in the Beach Tower, only steps away from all the Beach Villa amenities, is our professionally decorated, spacious, split bedroom layout villa. Offering the benefits of an open plan living space and seamlessly flowing on to the lanai, Hale...

    Pool Hot Tub

    $427 to $1,268/night

  26. CONDOMINIUM
    Honua Kai 346

    Honua Kai 346

    Lahaina, HI

    We invite you to stay in our gorgeous ocean view 1 bedroom/1 bathroom condo at Honua Kai! Enjoy the sparkling blue water views from the open lanai and the bedroom, bringing a total sense of relaxation to your time in Maui. Honua Kai 346 is one of...

    Pool Hot Tub
    FREE CANCELLATION

    $427 to $1,044/night

  27. CONDOMINIUM
    Honua Kai 520

    Honua Kai 520

    Lahaina, HI

    What sounds better than waking up to a hot cup of delicious coffee on a lanai that opens up to sweeping views of the majestic West Maui mountains? We invite you to indulge in the authentic Maui lifestyle, making our Honua Kai 520K your home away...

    Pool Hot Tub
    FREE CANCELLATION

    $427 to $1,169/night

  28. HOUSE
    Hilo Shangrila

    Hilo Shangrila

    Keaau, HI

    Let the oceanfront, gated retreat of Hilo Shangrila envelope you, with its private saltwater pool, hot tub, and covered lanai, all just a stone's throw from the peaceful Pacific. New air conditioning has been added in all bedrooms for total guest...

    Pool Hot Tub

    $423 to $571/night

  29. CONDOMINIUM
    Hanalei Bay Resort 6301-2

    Hanalei Bay Resort 6301-2

    Princeville, HI

    This unit has among the most extraordinary views in the entire resort. A top floor unit, the view from every room is exceptional, encompassing the entire expanse of the bay, from the mountains behind Hanalei to “Bali Hai” peak and the ocean...

    Pool Hot Tub

    $422 to $482/night

  30. CONDOMINIUM
    Kaanapali Royal #A201 (MAUI)

    Kaanapali Royal #A201 (MAUI)

    Lahaina, HI

    FALL SPECIAL! 10% off until the end of November! Experience five-star Maui luxury at an affordable price! This modern ground-floor unit at Kaanapali Royal features a spacious floor plan that opens to sweeping golf course views. Extensively...

    Pool Hot Tub

    $421 to $1,188/night