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
    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 $3,365/night

  2. HOUSE
    Kahakai Estates Hale

    Kahakai Estates Hale

    Kailua Kona, HI

    This charming home is ideally situated in the gated community of Kahakai Estates on the Big Island's spectacular Kona Gold Coast. Experience the seclusion of your own Hawaiian hideaway just two miles southwest of all the incredible attractions and...

    Pool Hot Tub

    $482 to $839/night

  3. 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 $3,546/night

  4. 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 $3,653/night

  5. VILLA
    Vacation Home in Ko Olina Resort

    Vacation Home in Ko Olina Resort

    Kapolei, HI

    Ko Olina Kai is a peaceful gated community that offers all the tranquil privacy you could desire! The interior is spacious and homey with 2 bedrooms, 2 baths, a living room with an adjacent dining space, and a kitchen. This outstanding villa offers...

    Pool Hot Tub
    FREE CANCELLATION

    $152 to $158/night

  6. APARTMENT
    Waikiki Grand 315 Studio

    Waikiki Grand 315 Studio

    Honolulu, HI

     Legally permitted vacation rental -  134 Kapahulu Ave  #315  Waikiki Grand - So close to Waikiki Beach & Everything else Waikiki Offers Fun Place to stay That really is close to Everything in Waikiki! This unit features breathtaking views of...

    Pool
    FREE CANCELLATION

    $124 to $179/night

  7. CONDOMINIUM
    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    Waikoloa, HI

    Discover the spirit of Aloha! Tucked away next to one of the Aloha states largest and most luxurious resorts, this 2 bedroom 2 bathroom villa is a destination in itself. Located on the golf course, and only a few minutes walk from the beach, there...

    Pool Hot Tub
    FREE CANCELLATION

    $172 to $431/night

  8. CONDOMINIUM
    Waikiki Banyan Tower 2 Suite 2904

    Waikiki Banyan Tower 2 Suite 2904

    Honolulu, HI

    Queen Sized Bed, Waikiki Banyan, Free WiFi and ParkingEnjoy a fully-equipped kitchen and comfortable seating in the living room. Kitchen includes refrigerator, range, microwave, rice maker, coffee maker, and other standard kitchen wares. All units...

    Pool Hot Tub

    $180 to $259/night

  9. CONDOMINIUM
    Waikiki Sunset WS 2404

    Waikiki Sunset WS 2404

    Honolulu, HI

    Partial Ocean View Waikiki Sunset Condo, Free Parking & WifiSoak in the view from this high level condo. The view from the lanai is of Diamond Head Crater and Kapiolani Park to the left and the ocean to the right. This condo suite is one block from...

    Pool

    $157 to $202/night

  10. CONDOMINIUM
    Bamboo 906 Condominium

    Bamboo 906 Condominium

    Honolulu, HI

     Legally permitted vacation rental -    2425 Kuhio Ave. Suite #906   Brand New split A/C - High efficiency ‘Super-cooling’ Air Conditioning system and New, quiet, double insulated sliding windows installed August 2019 Great New Studio Suite...

    FREE CANCELLATION

    $140/night

  11. CONDOMINIUM
    Waikiki Grand 312 Condo

    Waikiki Grand 312 Condo

    Honolulu, HI

     Legally permitted vacation rental -  134 Kapahulu Ave  #312  Queen size bed, full bathroom, kitchenette and great balcony - Great Price! A great place in a great location at a great price - Come join us Soon! My place is close to Only one...

    Pool
    FREE CANCELLATION

    $129 to $169/night

  12. APARTMENT
    WS2105 229 Paoakalani Ave Honolulu RFRF-CTOQ(RM)-00-ACH

    WS2105 229 Paoakalani Ave Honolulu RFRF-CTOQ(RM)-00-ACH

    Honolulu, HI

    World Famous Waikiki White Sandy Beaches only one block away,Incredible Views. Relax and enjoy all the fabulous amenities, New Gym onsite Sapphire Blue Tiled Pool, Tennis and Basketball Court, Sauna and Showers on the 6th floor, Bar-B-Que Picnic...

    Pool
    FREE CANCELLATION

    $211 to $374/night

  13. CONDOMINIUM
    Waikiki Grand 216 Hotel

    Waikiki Grand 216 Hotel

    Honolulu, HI

     Legally permitted vacation rental -  134 Kapahulu Ave  #216  A Super affordable, romantic Hideaway in the Heart of Waikiki next to Hula's Located at the Waikiki Grand Hotel & just 20ft from the world famous Hula's Bar & Lei Stand. Enjoy our...

    Pool
    FREE CANCELLATION

    $96 to $158/night

  14. CONDOMINIUM
    Kona Pacific B310

    Kona Pacific B310

    Kailua Kona, HI

    This tropically appointed 1 bedroom 2 bathroom unit is perfect for guests seeking a peaceful retreat minutes from the heart of Kailua Kona which offers a wide array of activities, restaurants, boutiques, and perfect place to take a stroll along Alii...

    Pool

    $239 to $522/night

  15. APARTMENT
    Diamond Head Beach Hotel 303

    Diamond Head Beach Hotel 303

    Honolulu, HI

     Legal vacation rental -  2947 Kalakaua Ave, #303  Whether for business or pleasure the delightful attention to detail Wins! Located at the foot of the iconic Diamond Head crater, this home away from home has everything you need for either...

    FREE CANCELLATION

    $153 to $219/night

  16. APARTMENT
    Tradewinds Plaza 304

    Tradewinds Plaza 304

    Honolulu, HI

     Legal vacation rental -  2572 Lemon Rd. #304  Tasteful, Total remodel Studio in Ideal location 1.5 mins from Waikiki Beach We are so lucky to be able to offer this fully remodeled studio, Queen bed studio at this great price. Not only are all...

    FREE CANCELLATION

    $158 to $203/night

  17. CONDOMINIUM
    Eldorado E104

    Eldorado E104

    Lahaina, HI

    Come enjoy your own piece of paradise!The weather is ideal in Maui year round. MAUI ELDORADO HAS THE ONLY PRIVATE BEACH CABANA ON KAANAPALI BEACH FOR MAUI ELDORADO GUESTS ONLY. Experience Maui Eldorado in the Heart of Kaanapali - an affordable...

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $554/night

  18. HOUSE
    Hale Poola

    Hale Poola

    Honolulu, HI

    This recently upgraded five bedroom, three bathroom home sits on a small hill in the quiet neighborhood of Aina Haina. Hale Poola comfortably sleeps 10 people, but will house up to 12. The large open living room, media room and kitchen create a nice...

    $890 to $1,302/night

  19. COTTAGE
    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    Kamuela, HI

    This spectacular 3 bedroom- 3 bath single-level cottage is located within Kamilo, which is nestled near the heart of the Mauna Lani Resort area. Upon entering Mauna Lani KaMilo Home (424) enjoy the vaulted ceilings and open floor plan which allows...

    Pool Hot Tub

    $481 to $1,285/night

  20. HOUSE
    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    Kailua Kona, 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

    $482 to $720/night

  21. CONDOMINIUM
    Mauna Lani Golf Villas C1

    Mauna Lani Golf Villas C1

    Kamuela, HI

    Our 2-story villa is the best unit in the Golf Villas! C1 is situated in a superior end villa location on the 10th fairway of the famed championship Francis H. I'I Brown South Course at Mauna Lani. The course was the former home to the annual Senior...

    Pool

    $427 to $720/night

  22. CONDOMINIUM
    Palms Waikiki 720

    Palms Waikiki 720

    Honolulu, HI

     Legally permitted vacation rental -     1850 Ala Moana Blvd, Suite #720  HOT NEW LISTING WITH AVAILABILITY! Stunning remodel, this sleek modern styled 7th floor suite comfortably accommodates two adults and is located steps from the Waikiki...

    Pool
    FREE CANCELLATION

    $168 to $197/night

  23. APARTMENT
    Waikiki Grand 908 Studio

    Waikiki Grand 908 Studio

    Honolulu, HI

     Legally permitted vacation rental -  134 Kapahulu Ave, #908  You can't beat the location & the views, plus the price is right too! One of the best Remodels in the Waikiki Grand - Enjoy true in-door / out-door Hawaii weather with the retracting...

    Pool
    FREE CANCELLATION

    $167 to $197/night

  24. CONDOMINIUM
    Diamond Head Beach Hotel 1203

    Diamond Head Beach Hotel 1203

    Honolulu, HI

     Legal vacation rental -  2947 Kalakaua Ave, #1203  A large one bedroom suite with full comfortable living room and dining area for up to four guests. The suite boasts gorgeous 12th floor panoramic views of both Diamond Head Crater and the...

    Pool
    FREE CANCELLATION

    $242 to $309/night

  25. CONDOMINIUM
    Ilikai Hotel 803

    Ilikai Hotel 803

    Honolulu, HI

    A King Size Bed & Futon at the Ilikai - Close to Everything & 2 Great Pools! A fully equipped nicely spaced one bedroom suite at the Hawaii Five'O famed Ilikai Hotel - Relax by one of the two pools, sip cocktails at Cinnamon's Bar & Restaurant or...

    Pool
    FREE CANCELLATION

    $167 to $219/night

  26. HOUSE
    Milo Hae Hale

    Milo Hae Hale

    Koloa, HI

    Enjoy the serenity and privacy of the Milo Hae Hale. This beautiful 3 bed 3 bath home features privacy and comfort nestled within the exclusive Kiahuna Golf Village community on Kauai's scenic and sunny South Shore. Enjoy the 1990 square foot...

    Pool

    $661 to $1,854/night

  27. 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

  28. 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

    $1,703 to $4,290/night

  29. VILLA
    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    Waikoloa, HI

    This Villa is in an excellent location right at one of the two lava rock pools that Waikoloa Beach Villas has to offer. The property is located on the ground floor which comes with many benefits. No stairs to climb, which makes bringing groceries...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $431/night

  30. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Wonderful ocean views from this spacious penthouse level studio. The owners have completed a beautiful remodel featuring tile floors and a new sofa-sleeper. The full kitchen was recently re-done with new appliances, granite counter tops, new...

    Pool Hot Tub
    FREE CANCELLATION

    $185 to $614/night