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. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Located on Kohala Coast on the Big Island of Hawaii, this luxurious private home is just a short golf cart ride away from the premier Mauna Kea Golf Course. It is beautifully appointed with spectacular views of the ocean and the Mauna Kea and Hapuna...

    Pool Hot Tub

    $4,524 to $4,955/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

    $3,695 to $6,075/night

  5. 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

    $3,398 to $7,265/night

  6. VILLA
    Wailea Inn Villa, 14 Bedrooms w/ Pool, Hot Tub & Yoga Studio- St

    Wailea Inn Villa, 14 Bedrooms w/ Pool, Hot Tub & Yog...

    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

  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. 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

    $1,971 to $3,125/night

  9. 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

    $1,968 to $3,075/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

    $1,938 to $3,030/night

  11. 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

  12. 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 2017,...

    Pool

    $1,910 to $3,695/night

  13. VILLA
    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps To Beach

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps ...

    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...

    $1,855 to $3,392/night

  14. 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

    $1,683 to $2,076/night

  15. HOUSE
    House of the Turtle at Champion Ridge, Mauna Lani (CR 18)

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

    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

    $1,672 to $3,695/night

  16. 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

    $1,661 to $2,429/night

  17. 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

    $1,624 to $4,290/night

  18. 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

    $1,559 to $3,517/night

  19. 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

  20. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Welcome to Hale Lani. This gorgeous house is a Brand New Vacation Rental that Knutson & Associates Management is proud to represent. Hale Lani is the perfect spot to host a unforgettable Hawaii Vacation. With 4 bedrooms, and a capacity to sleep 14,...

    Pool
    FREE CANCELLATION
  21. 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

    $1,458 to $2,694/night

  22. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    'Kona Bubbles' is a absolute spectacular property that Knutson & Associates is extremely proud to be newly representing as of November 2018. A gorgeous home in gated Meilani View Estates with ocean views just above Kailua Kona. Recently finished in...

    Pool
    FREE CANCELLATION
  23. 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

    $1,351 to $4,811/night

  24. 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...

    $1,343 to $2,014/night

  25. 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

  26. HOUSE
    Hahalua Hale

    Hahalua Hale

    Kailua Kona, HI

    Welcome to "Hahalua Hale" (House of the Manta Ray) located in a quiet gate community. Located at a perfect coffee growing elevation that receives those cool tropical Hawaiian breezes, this magnificent, one-of-kind, architectural showpiece sited for...

    Pool

    $1,261 to $1,664/night

  27. 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 $3,993/night

  28. 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 $3,772/night

  29. 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

    $1,168 to $2,876/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 $4,083/night