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
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Kauhale Pilialoha Indulge yourself in the ultimate in island style luxury, at the Big Island of Hawaii’s most exclusive retreat – Kauhale Pilialoha.  Experience breathtaking sunsets and enjoy the natural beauty of Hawaii from the ultimate...

    Pool Hot Tub

    $18953 to $29061/night

  2. ESTATE
    Mauna Kea Bluffs #5: La Ikena O Komohana

    Mauna Kea Bluffs #5: La Ikena O Komohana

    Kamuela, HI

    Found on the sunny Kohala Coast of the Big Island of Hawaii, the Mauna Kea Bluffs #5 estate is conveniently located within an exclusive gated community. This magnificent estate home boasts 11,500 square feet of interior space. Every detail has been...

    Pool Hot Tub

    $10310 to $12690/night

  3. ESTATE
    Kailua Shores Estate

    Kailua Shores Estate

    Kailua, HI

    One of the largest, most private and secluded Estates on the island of Oahu. A spectacular beachfront location-at Kailua Shores Estate with the comfort of a resort, consisting of separate houses, newly remodeled, set on extensive grounds featuring a...

    Pool

    $7930 to $11500/night

  4. APARTMENT
    Waikiki Grand View Penthouse

    Waikiki Grand View Penthouse

    Honolulu, HI

    Gateway to World Famous Waikiki! This luxury 38th floor Penthouse is in Honolulu's prestigious Waikiki Landmark, presenting exquisite and classical finishes and orchestra views of the finest beaches, shops, and restaurants of Waikiki.  Relish in...

    Pool

    $3468 to $7335/night

  5. VILLA
    Remodeled Kihei Villa

    Remodeled Kihei Villa

    Kihei, HI

    This is a luxury vacation villa perfect for your family celebration or getaway retreat. The villa has four separate newly remodeled units, each with their own private lanai (patio). The whole Villa has a total of 12 bedrooms, 2 separate loft...

    Pool

    $3248 to $5568/night

  6. HOUSE
    Ali’i Honu Kai House

    Ali’i Honu Kai House

    Kailua-Kona, HI

    Perfectly located on the Kona “Gold Coast” of the Big Island between the charming village of Kailua~Kona and Keahou Bay, this home offers you your own personal paradise. From the moment you drive up to this dramatic gated, Ocean Front Estate you...

    Pool

    $3025 to $4840/night

  7. HOUSE
    Blue Lagoon

    Blue Lagoon

    Kamuela, HI

    A Polynesian resort inspired estate with large heated pool and spa, ideal for a spacious getaway or large group. Upon entering through 10 ft mahogany gates, traversing a bridge over a Koi pond past a waterfall, you will be treated to the luxury...

    Pool Hot Tub

    $2813 to $5955/night

  8. TOWNHOUSE
    Kaunaoa 7B at Mauna Kea Resort (4BR/4.5BA)

    Kaunaoa 7B at Mauna Kea Resort (4BR/4.5BA)

    Kamuela, HI

    This luxury two-story townhome features four bedrooms (including two master suites) and 4.5 baths, with its own private pool and spa, in an exclusive gated community. Only about 500 yards from two exceptional resorts and two of the most renowned...

    Pool

    $2575 to $4360/night

  9. VILLA
    Hale Waiulu #150470

    Hale Waiulu #150470

    Kailua Kona, HI

    Our well-appointed home has everything you could possible need. Fresh, home grown mango, guava and finger lime for our guests to feast on . Enjoy the relaxing sound of the cascading rush of your private pool's waterfall. The lush golf green views of...

    Pool Hot Tub

    $2274 to $6318/night

  10. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Hale Pua (“House of Flowers”) now features AC as an option in all of its sleeping areas: five king bedrooms, one bunkroom with four twin beds and game room with queen sofabed. This special home is maybe the only 6 bed/6 full bath oceanfront...

    Pool

    $2212 to $3444/night

  11. VILLA
    Lele Penthouse Villa #336788

    Lele Penthouse Villa #336788

    Kihei, HI

    Lele Penthouse, located at the top of our grand staircase at the second level is this a luxurious penthouse with 4 bedrooms and 2 loft sleeping areas. Four bedrooms on the main floor, and two of these have your choice of King beds or 2 Twins. The...

    Pool

    $1995 to $3392/night

  12. HOUSE
    Lanikai Breeze

    Lanikai Breeze

    Kailua, HI

    Just steps away from coveted Lanikai Beach, sits our newest luxury rental - Lanikai Breeze. Built in 2017, this brand new construction boasts upgraded appliances and furnishings meticulously hand picked by local designer, Lotus Home Staging....

    Pool

    $1980 to $3765/night

  13. 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

    $1968 to $3075/night

  14. HOUSE
    Home of the Hula Moon

    Home of the Hula Moon

    Waimea, HI

    Stately and serene, Hula Moon sits on one of the most beautiful properties in Puako. Located at the quiet end of the road, you will enjoy year-round sunsets and privacy. As you enter through the gates, lush tropical plantings enhance the large...

    Pool

    $1876 to $2662/night

  15. HOUSE
    Papaua Estate

    Papaua Estate

    Lahaina, HI

    APPROVED MAUI SHORT TERM RENTAL HOUSE #STWM 2104/0003. You and your family and friends will love your stay here for a vacation filled with Aloha! If you are looking for location, luxury and Hawaiian life style, you have found it. Perhaps the most...

    Hot Tub
    FREE CANCELLATION

    $1869 to $2874/night

  16. VILLA
    Hualalai Resort Ocean Front Golf Villa 4202

    Hualalai Resort Ocean Front Golf Villa 4202

    Kailua Kona, HI

    Whale watch while listening to the breaking waves from the shoreline from the Master bedroom's private lanai with unobstructed ocean views! This beautifully appointed three bedroom villa has over 2,500 square feet of living area. Each of the three...

    FREE CANCELLATION

    $1751 to $5546/night

  17. HOUSE
    Rainbow Hale Estate

    Rainbow Hale Estate

    Lahaina, HI

    Maui's Premier Vacation Home! Rainbow Hale Estate Kaanapali! Family Retreat, Private Honeymoon Retreat! Surrounded by 5 acres of Maui tropical plantation, lies a BRAND NEW spectacular estate you've always dreamed of, with the lifestyle you've always...

    Pool

    $1661 to $2429/night

  18. HOUSE
    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    Princeville, HI

    This custom designed home by Hawaii’s renowned architect Mark Eyler is located on the idyllic northshore of Kauai. Designed for professional surfer Bruce Irons, the architecture and interior design blends Balinese, Hawaiian and Asian elements with...

    Pool

    $1623 to $3408/night

  19. HOUSE
    Hale O'Pulelehua

    Hale O'Pulelehua

    Hanalei, HI

    Hale O'Pulelehua, 50 Steps to Amazing Banana Beach! TVNC: 1238 A classic plantation style home, this Haena beach house, known as Hale Pulelehu'a (The Butterfly House), is a wonderful place for your family & friends to experience the island...

    $1623 to $3816/night

  20. HOUSE
    Hale O'Pulelehua with Guest House

    Hale O'Pulelehua with Guest House

    Hanalei, HI

    Hale Pulelehua with Guest House - less than a minute walk to Amazing Banana Beach!TVNC: 1238 A classic plantation style home, this Haena beach house, known as Hale Pulelehu'a (The Butterfly House), is a wonderful place for your family & friends to...

    $1623 to $3816/night

  21. HOUSE
    Hokulani

    Hokulani

    Honolulu, HI

    Hokulani, Hawaiian for “heavenly star,” is your next luxury vacation destination. New to the market, Hokulani is a relaxing executive estate in the heart of upscale Kahala. This meticulously planned estate furnished by the premier Orange...

    Pool Hot Tub

    $1623 to $4152/night

  22. 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
    FREE CANCELLATION

    $1506 to $4833/night

  23. HOUSE
    Indo Lotus Beach House

    Indo Lotus Beach House

    Wailea, HI

    The Indo Lotus Beach House is one of the few vacation homes on Maui that has a legal grandfathered rental history, combined with a beachfront location. Set on Kamaole One Beach at the 'Charley Young' end, Indo Lotus has direct access to a popular...

    Hot Tub

    $1454 to $2356/night

  24. VILLA
    Hualalai Resort Palm Villa 140B

    Hualalai Resort Palm Villa 140B

    Kailua-Kona, HI

    This Hualalai Palm Villa is a spectacular three bedroom, three bath, two-story Hualalai condo on popular Waiulu Street at the world renowned Hualalai Resort. The Resort is home to the Four Seasons Hualalai, regarded by many as the #1 Resort in...

    Pool
    FREE CANCELLATION

    $1401 to $3736/night

  25. TOWNHOUSE
    Hualalai Resort Haliipua Villa 104

    Hualalai Resort Haliipua Villa 104

    Kailua-Kona, HI

    Built in 2009, Haliipua Villas are the newest generation of multi-family villas at Hualalai offering an array of designer finishes throughout the home. Special features include luxurious mahogany finishes, island-inspired ceiling treatments,...

    FREE CANCELLATION

    $1401 to $3736/night

  26. HOUSE
    Hale Keanu- Waimea Home

    Hale Keanu- Waimea Home

    Waimea, HI

    Sweeping Ocean Views & Separate Ohana. Rare 4 bedroom - Wai'ula'ula at Mauna Kea Step into a dream at an exceptional four-bedroom ocean-view rental at Wai'ula'ula within the Mauna Kea Resort. At this single level brand-new home, you will find a...

    Pool Hot Tub

    $1390 to $3032/night

  27. HOUSE
    Mauna Kea Fairways North #9

    Mauna Kea Fairways North #9

    Kamuela, HI

    The vacation of a lifetime awaits at Mauna Kea Fairways North, a gated community within the premier resort area of Hawaii Island. Mauna Kea Fairways North #9 boasts three en suite bedrooms, air conditioning, a private pool and spa, and views of the...

    Pool Hot Tub

    $1385 to $1861/night

  28. HOUSE
    The Oasis

    The Oasis

    Kamuela, HI

    Remodeled and redecorated in 2018, The Oasis boasts vaulted ceilings, tropical hardwoods, marble and granite counter tops, air conditioning, and expansive living spaces with plenty of luxurious seating. Along with a professional chef’s kitchen, an...

    Pool

    $1384 to $2811/night

  29. CONDOMINIUM
    Wailea Elua Unit #1305

    Wailea Elua Unit #1305

    Wailea, HI

    A note from the owner: Wailea Elua Village #1305 boasts 3 bedrooms (king bed in the master, queen bed in the 2nd bedroom and 2 twin beds in the 3rd bedroom) and a prime oceanfront ground floor location just steps from the white sands of Elua Beach....

    Pool

    $1346 to $2076/night

  30. HOUSE
    Kona Bay Bliss

    Kona Bay Bliss

    Kailua Kona, HI

    This incredible home is secluded in a 24 hour guard gated oceanfront community, yet is close to all that Kona has to offer. It is located just a short walk from the classic old Hawaiian town of Kailua and the start/finish of the Ironman. In all of...

    $1343 to $2014/night