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
    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

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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

  9. 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

  10. 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

  11. 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 $3,796/night

  12. 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

  13. 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 $3,356/night

  14. 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 $3,456/night

  15. 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

  16. 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 $3,183/night

  17. 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 the...

    $1,018 to $1,315/night

  18. 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
  19. 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...

    $869 to $1,315/night

  20. HOUSE
    Hale A Kai

    Hale A Kai

    Princeville, HI

    This beautiful custom home is located in the Queen Emma Bluff's gated community in Princeville. The home is approximately 4000 sq feet. Upstairs is a large great room with beautiful hardwood floors. There’s a well equipped gourmet kitchen with a...

    $842 to $1,149/night

  21. CONDOMINIUM
    O-1202: Hale Pumehana Ko Olina Beach Villa

    O-1202: Hale Pumehana Ko Olina Beach Villa

    Kapolei, HI

    This 3 BD, 2.5 BA luxury Penthouse on the 12th floor of the Ocean Tower has stunning direct ocean views, was fully re-decorated by a professional interior designer in early 2015 (NEW paint, furnishings, original artwork, built-in closets,...

    Pool

    $740 to $1,668/night

  22. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kalilua Kona, HI

    What is better than a Hawaiian sunset over the ocean? A sunset over the ocean that you can take in from the privacy of your tropical home-away-from-home! With nearly 5,000 square feet of indoor/outdoor living space, including a lanai with a pool...

    Pool

    $727 to $1,769/night

  23. CONDOMINIUM
    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    Kapolei, HI

    The Hale Nani Ikena Kai beach villa at Ko Olina offers exactly what its name suggests; a home with a “Beautiful Ocean View”. Spectacular direct whitewater ocean and beach views will be what greets you at this upscale, luxurious ground floor...

    Pool Hot Tub

    $682 to $2,016/night

  24. CONDOMINIUM
    Ko Olina Beach Villa (O121)

    Ko Olina Beach Villa (O121)

    Kapolei, HI

    Celebrities want privacy and quick exit routes, but so does everyone else! You deserve this one-of-a-kind Ko Olina Beach Villa, unlike any other located within the resort. It boasts over 1600 sq.ft of living space, 3 ground floor private lanais, no...

    Pool Hot Tub

    $682 to $1,668/night

  25. HOUSE
    Ainamalu Home 69-9242

    Ainamalu Home 69-9242

    Waikoloa Village, HI

    Come and enjoy a luxurious laid-back island living in our new home located in the beautiful new neighborhood in Waikoloa Beach Resort – Ainamalu. This gated community Ainamalu is the newest resort community in the beautiful Waikoloa Beach Resort,...

    FREE CANCELLATION

    $649 to $896/night

  26. HOUSE
    Ohana Kamalani

    Ohana Kamalani

    Princeville, HI

    This week only 15% off April and May dates. Situated in the heart of Princeville on the renowned Makai Golf Course, this luxury vacation rental with Bali Hai and ocean views offers ample space to comfortably accommodate eight guests. Complete with...

    Pool

    $571 to $1,570/night

  27. CONDOMINIUM
    O-226: Hale Ka Wailele Malu Ko Olina Beach Villa

    O-226: Hale Ka Wailele Malu Ko Olina Beach Villa

    Kapolei, HI

    Hale Ka Wailele Malu is one of the most unique and desirable Beach Villas in all of Ko'Olina. The large (1,650 sq ft) 3 bedroom, 3 bathroom, 2nd floor, ocean-facing Beach Villa is one of only four Villas (out of the 247) that fronts the soothing and...

    Pool Hot Tub

    $543 to $1,668/night

  28. CONDOMINIUM
    B-904: Hale Kai Ko Olina Beach Villa

    B-904: Hale Kai Ko Olina Beach Villa

    Kapolei, HI

    Beachfront Living at its finest! This 3 bedroom, 3 bath Villa is located in the beautiful Ko Olina Resort on the quiet West side of Oahu. The Beach Villas are the newest, and only, beachfront condominiums available on the island in 25 years....

    Pool Hot Tub

    $543 to $1,784/night

  29. CONDOMINIUM
    B-801: Hale Ohana Ko Olina Beach Villa

    B-801: Hale Ohana Ko Olina Beach Villa

    Kapolei, HI

    Experience the ultimate in oceanfront resort living in this beautiful and spacious vacation home located in the Beach Villas at Ko Olina! This 3 BR, 3 BA luxury villa on the 8th floor of the Beach Tower is conveniently located just 20 miles from...

    Pool Hot Tub

    $543 to $1,784/night

  30. HOUSE
    Ocean Soul (Big Island)

    Ocean Soul (Big Island)

    Ookala, HI

    Whether adventure or a relaxing vacation calls, Ocean Soul is the perfect place for your next Hawaiian retreat. Perched on the cliffside of Waipunalei, Ocean Soul's 13 acre property hosts the most amazing ocean views, a lap swimming pool,...

    Pool

    $530 to $780/night