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

    $17,975 to $27,561/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. APARTMENT
    Waikiki Grand View Penthouse

    Waikiki Grand View Penthouse

    Honolulu, HI

    div class="yiv6500686381" style="margin:0in 0in 0.0001pt; text-align:start; -webkit-text-stroke-width:0px"> Gateway to World Famous Waikiki! This luxury 38th floor Penthouse is in Honolulu's prestigious Waikiki Landmark, presenting exquisite and...

    Pool

    $3,398 to $7,265/night

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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

    $1,917 to $5,992/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
    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

  11. 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

  12. 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

    $1,751 to $5,546/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
    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

  15. 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

  16. 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

    $1,401 to $3,736/night

  17. HOUSE
    CR 18 House of the Turtle at Champion Ridge, Mauna Lani

    CR 18 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

  18. 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

    $1,341 to $4,696/night

  19. 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

  20. VILLA
    Hualalai Resort Fairway Villa 116D

    Hualalai Resort Fairway Villa 116D

    Kailua-Kona, HI

    Located on popular Waiulu Street just three minutes by golf cart to the Four Seasons Resort Hualalai, this large three bedroom single-level villa offers views of the 15th hole of the Hualalai Golf Course and ocean beyond. The villa is professionally...

    Pool
    FREE CANCELLATION

    $1,284 to $3,736/night

  21. CONDOMINIUM
    WPH1507 THTC-CTOQ(XS)-STALL-ACH

    WPH1507 THTC-CTOQ(XS)-STALL-ACH

    Honolulu, HI

    This privately owned 1 bedroom condo fully furnished and fully equipped providing a private "Home Away From Home" experience. This one bedroom suite is prefect for the traveler who wants to be in a full apartment in the center of Waikiki with FREE...

    Pool
    FREE CANCELLATION
  22. 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

  23. HOUSE
    Aina Malia (4-Bedroom Home)

    Aina Malia (4-Bedroom Home)

    Waimea, HI

    This unique property is situated above beautiful Wailea Bay on the Kohala Coast of the Big Island of Hawaii, one of the few white sand beaches on the island of Hawaii. Beautiful tropical landscaping abounds with privacy and romance. Custom designed...

    $1,204 to $2,420/night

  24. 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

    $1,198 to $2,876/night

  25. 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

  26. 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

  27. VILLA
    Hualalai Palm Villa 140C

    Hualalai Palm Villa 140C

    Kailua-Kona, HI

    The spacious floor plan includes a downstairs master bedroom suite with king bed and luxury spa-like bath. Just off the master is a large living room with queen sized sofa pull out that opens to the downstairs lanai, leading to the lawn and golf...

    Pool
    FREE CANCELLATION

    $1,168 to $3,736/night

  28. VILLA
    Hualalai Resort- Palm Villa 130A

    Hualalai Resort- Palm Villa 130A

    Kailua-Kona, HI

    One of the largest floor plans of any villa at Hualalai, this spacious and centrally located 3 bedroom, 3 bath villa is ideal for your Hawaii getaway. Extra bedding available with a "bonus" living room on the first level. The down-stairs suite opens...

    Pool
    FREE CANCELLATION

    $1,168 to $3,736/night

  29. VILLA
    Hualalai Resort- Waiulu 137D

    Hualalai Resort- Waiulu 137D

    Kailua-Kona, HI

    This spacious 3 bedroom, 3.5 bath single-level villa is centrally located on the Resort’s popular Waiulu Street overlooking beautiful Punawai Pond, the 5th Hole of the Member’s Ke`olu Golf Course and the ocean beyond. With 2642 square feet of...

    Pool
    FREE CANCELLATION

    $1,168 to $3,736/night

  30. 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