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

    $18,953 to $29,061/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

    $10,240 to $12,620/night

  3. VILLA
    Wailea Inn Villa

    Wailea Inn Villa

    Kihei, HI

    Wailea Inn 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). Each of the four units may be rented separately or in any...

    $3,248 to $5,568/night

  4. VILLA
    Kahala Grand Splendor

    Kahala Grand Splendor

    Honolulu, HI

    Admiration starts at first glance with this contemporary vacation residence, completed in 2015 and boasting a huge pool, luxurious rooms with extravagant details, and central air conditioning. The tone of the home is set by a custom, solid mahogany...

    Pool Hot Tub

    $3,100 to $4,766/night

  5. 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

    $2,212 to $3,444/night

  6. 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

    $2,022 to $6,318/night

  7. HOUSE
    Hale Nui 2827

    Hale Nui 2827

    Lahaina, HI

    Thoughtfully designed with your comfort in mind, Hale Nui will exceed your expectations! After a long, arduous flight, each guest will feel embraced upon entering this exquisite, spacious home and everyone will immediately marvel at the panoramic...

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  8. VILLA
    Lele Penthouse

    Lele Penthouse

    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...

    $1,995 to $3,392/night

  9. HOUSE
    Lanikai Breeze

    Lanikai Breeze

    Kailua, HI

    Spring Break Specials - 15% OFF RATES - NOW until March 6th (Promo valid on travel dates from March 15th - April 15th) Just steps away from coveted Lanikai Beach, sits our newest luxury rental - Lanikai Breeze! Brand new construction, built in...

    Pool

    $1,910 to $3,695/night

  10. 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

    $1,876 to $2,662/night

  11. 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

    $1,869 to $2,874/night

  12. 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 Pets OK

    $1,821 to $4,082/night

  13. HOUSE
    Hale Pulelehua

    Hale Pulelehua

    Hanalei, HI

    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 lifestyle on the North Shore of Kauai. Immaculately cared...

    $1,553 to $3,408/night

  14. 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 a...

    Pool

    $1,553 to $3,338/night

  15. HOUSE
    Hale Pulelehua with Guest House

    Hale Pulelehua with Guest House

    Hanalei, HI

    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 lifestyle on the North Shore of Kauai. Immaculately cared...

    $1,553 to $3,408/night

  16. HOUSE
    House of the Turtle at Champion Ridge, Mauna Lani

    House of the Turtle at Champion Ridge, Mauna Lani

    Kamuela, HI

    Tranquility and luxury await in this single-level residence with spectacular Kohala Mountain views in the desirable gated Champion Ridge community. Situated in the heart of Mauna Lani, for convenient access to the finest beaches, golf, restaurants,...

    Pool Hot Tub

    $1,391 to $2,985/night

  17. 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

    $1,315 to $3,695/night

  18. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Relax and luxuriate in this spacious and bright four bedroom luxury property, newly renovated, redesigned and brand new to the rental market! Professional and cheerful Fine Design interior decor echoes tones of the nearby Pacific. Unwind on the...

    Pool Hot Tub

    $1,267 to $3,815/night

  19. 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

    $1,264 to $3,032/night

  20. HOUSE
    Pua Lani Home 69-1854

    Pua Lani Home 69-1854

    Waimea, HI

    A sophisticated touch of "old Hawaii" with easy ocean front living.  Large open spaces, Ocean views from two master suites, kitchen and living room with expansive covered lanai across the ocean side of the home.  Enter into two private landscaped...

    Pool

    $1,210 to $2,420/night

  21. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Relax in your own private pool and waterfall spa on a spacious deck while enjoying some of the best panoramic ocean, coastline, sunset, and Maui views in the entire Mauna Kea Resort. This exquisite luxury property, recently renovated and refreshed...

    Pool Hot Tub

    $1,191 to $3,569/night

  22. HOUSE
    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    Kamuela, HI

    This golf course-adjacent luxury home in a gated oceanfront community is the premier destination for a once-in-a-lifetime Hawaiian getaway. Offering over 3,000 square feet of island elegance with stunning views, a private pool and hot tub, and...

    Pool Hot Tub

    $1,182 to $3,373/night

  23. HOUSE
    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    This elegant and timeless oceanfront estate is situated on the scenic shores of beautiful Puako Bay. One of Hawaii's last remaining peaceful little beach communities, Puako is steeped in history from abundant fishing to sugar cane farming and epic...

    $1,160 to $3,474/night

  24. HOUSE
    Hawaii Happy Healthy House

    Hawaii Happy Healthy House

    Waimea, HI

    Hawaii Happy Healthy House is a five bedroom, five bathroom (plus powder room) located in the exclusive, gated Kohala Ranch community on the Big island of Hawaii. The Kohala Coast is one of the sunniest destinations in Hawaii with a unique blend of...

    Pool Hot Tub

    $1,089 to $1,513/night

  25. HOUSE
    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    This oceanfront Kohala Coast home with breathtaking coastline views offers the ultimate setting for a once-in-a-lifetime escape to paradise. Decorated in a tranquil, elegant island style, it features two master suites, central air conditioning, and...

    $1,077 to $3,201/night

  26. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    Kailua Kona, HI

    Among the newest additions to the exclusive Four Seasons Resort Hualalai, this ocean-view villa provides the perfect setting for a romantic getaway for two or a relaxing retreat to paradise for two couples. The villa boasts over 2,600 square feet of...

    Pool Hot Tub

    $1,056 to $3,132/night

  27. CONDOMINIUM
    Ocean View Beachfront Beach Level 4-Bed Turtle Bay Villa 104

    Ocean View Beachfront Beach Level 4-Bed Turtle Bay Villa...

    Kahuku, HI

    Ocean View & Beachfront Beach Level 4-Bedroom (2 Masters) Turtle Bay Villa 104 At Ocean Villa 104 you have dramatic ocean views from just about everywhere! My 4-bedroom villa is located on the beach level so you can walk right out your living room...

    Pool Hot Tub

    $1,037 to $3,517/night

  28. TOWNHOUSE
    Hale Lani Ko Olina Kai Villa (1077E)

    Hale Lani Ko Olina Kai Villa (1077E)

    Kapolei, HI

    At Hale Lani Villa, you can walk to the beach in 10 minutes or drive there in 2! The 3 BR, 2 BA villa is conveniently located just 20 miles from Honolulu International Airport on the beautiful southwestern shores of Oahu. The resort offers four...

    Pool
  29. VILLA
    3BD Fairways Villa (116C) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116C) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Make memories with family and friends in this spacious Waiulu Street ground floor villa, overlooking the 15th hole of the Jack Nicklaus Hualalai Golf Course with the Pacific Ocean and Mount Hualalai beyond. The home features an open floor plan, high...

    Pool Hot Tub

    $970 to $2,856/night

  30. ESTATE
    Hale Kauka

    Hale Kauka

    Kamuela, HI

    ***Please note there is a 7 night minimum during the holidays. Christmas reservations must check out by 10AM on Dec. 27 and New Year's reservations can check in on Dec. 27 or after for a week. There is a 14 night minimum to book both Christmas and...

    Pool

    $958 to $1,375/night