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
    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

  2. 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

    $1337 to $3873/night

  3. HOUSE
    Paina Hale

    Paina Hale

    Waialua, HI

    Welcome to the Paina Hale – 3,900sq ft (363m2) Oceanfront beach house in Mokuleia, Oahu. The Paina Hale is a gated, 3-story beach house surrounded by tropical landscaping. The property offers complete privacy and is a perfect place for a family...

    $1326 to $2516/night

  4. APARTMENT
    Waikiki Banyan #2206

    Waikiki Banyan #2206

    Honolulu, HI

    Enjoy this one bedroom suite located on the 22nd floor facing South with awesome Ocean Views. This is a large one bedroom corner unit that has been beautifully remodeled including ceramic tile and wood flooring, paint, kitchen cabinets, bathroom...

    FREE CANCELLATION
  5. CONDOMINIUM
    Waikiki Park Heights #1507

    Waikiki Park Heights #1507

    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
  6. 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

    $1284 to $3736/night

  7. 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

    $1261 to $1664/night

  8. 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

    $1261 to $3628/night

  9. VILLA
    Kapalua Bay Villa 21B2

    Kapalua Bay Villa 21B2

    Kapalua, HI

    This gorgeous Beach Front Villa occupies the top two floors of building 21. It has two completely private master bedrooms with en-suite. Main floor master has a private lanai. Both master suites have spectacular ocean views. There are 3 bathrooms;...

    Pool

    $1254 to $1898/night

  10. 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

    $1252 to $3645/night

  11. 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...

    $1230 to $3575/night

  12. 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

    $1210 to $2420/night

  13. 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...

    $1204 to $2420/night

  14. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Why book individual resorts or condos when your whole group can enjoy a mansion in paradise? Enjoy exceptional panoramic coastal views from the private and quiet custom home at the O’oma Plantation. This large home is the perfect escape for a...

    Pool

    $1179 to $1664/night

  15. 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

    $1168 to $3736/night

  16. 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

    $1168 to $3736/night

  17. 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

    $1168 to $3736/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

    $1168 to $3647/night

  19. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Experience a vacation of a lifetime in this massive oceanfront custom home tucked away in an exclusive and quiet gated community along the Kona coast. A pond with a waterfall, filled with flowers welcomes you upon entering this beautiful custom...

    Pool Hot Tub

    $1150 to $1605/night

  20. 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...

    $1147 to $3299/night

  21. VILLA
    Hali'ipua Villa #108

    Hali'ipua Villa #108

    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

    $1126 to $3191/night

  22. CONDOMINIUM
    Honua Kai Konea 1019

    Honua Kai Konea 1019

    Kaanapali, HI

    Unbelievable KONEA 10th FLOOR CORNER PENTHOUSE -PANORAMIC VIEWS above the resort not looking into the courtyard. The 180 degree view of the blue pacific ocean, the islands of lanai and molokai, Black Rock and Maui Mountains! One of only four homes...

    Pool Hot Tub
    FREE CANCELLATION

    $1114 to $3363/night

  23. VILLA
    Hualalai Resort Ke Alaula Villa 210A

    Hualalai Resort Ke Alaula Villa 210A

    Kailua-Kona, HI

    Spectacular three bedroom three bath villa centrally located within the Hualalai Resort. Two story townhome style in the exclusive Ke Alaula neighborhood, just a 3-4 minute cart ride to the Four Seasons Hotel. Fully receding pocket glass, screen and...

    FREE CANCELLATION

    $1109 to $3736/night

  24. VILLA
    Hualalai Resort Hillside 4102

    Hualalai Resort Hillside 4102

    Kailua-Kona, HI

    Location-Location-Location! This spectacular 2 bedroom, 2 bath luxury villa is a short distance to the Four Seasons Resort Hualalai - truly one of the worlds' great resorts. Enjoy the soothing sounds of gentle waves on the shoreline from this ground...

    Pool
    FREE CANCELLATION

    $1109 to $3736/night

  25. 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

    $1089 to $1513/night

  26. CONDOMINIUM
    Whaler at Kaanapali Beach 852

    Whaler at Kaanapali Beach 852

    Lahaina, HI

    Sweeping Ocean Views from Molokai to Lanai from this 8th floor Ocean Front condo. Floor to ceiling windows and doors bring the ocean views into the living area and the bedrooms. Ocean views can be enjoyed from the king bed in the master bedroom. The...

    Pool Hot Tub
    FREE CANCELLATION

    $1089 to $1445/night

  27. CONDOMINIUM
    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    Lahaina, HI

    Ocean Front like you’ve never seen before! Located on the end of the building, this condo sits right on the world famous, Ka’anapali Beach. Enjoy spectacular ocean views from each room, whether you are relaxing on the couch, lying in bed or...

    Pool
    FREE CANCELLATION

    $1089 to $1445/night

  28. HOUSE
    Lanikai La'i Hale

    Lanikai La'i Hale

    Kailua, HI

    Enjoy ocean views from every room featured in this home with panoramic views from Kailua to Lanikai.  With magical sunrises over the Mokulua islands and sunsets over Pillbox hike.  This home set atop the hillside of Lanikai provides privacy from...

    $1088 to $1385/night

  29. VILLA
    Fairways Villa 116C

    Fairways Villa 116C

    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

    $1040 to $2918/night

  30. ESTATE
    Hale Kauka

    Hale Kauka

    Kamuela, HI

    Welcome to Hale Kauka, in the quaint town of Puako.  Located on the Big Island’s Kohala coast, Hale Kauka is one of the few ocean front properties in the area that has access to a small sandy beach right off the backyard! This home is located on...

    Pool Hot Tub

    $1028 to $1445/night