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
    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

  2. 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

    $1,089 to $1,445/night

  3. 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

    $1,089 to $1,445/night

  4. 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

    $1,037 to $3,517/night

  5. 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
  6. VILLA
    3BD Fairways Villa (116C) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116C) at Four Seasons Resort Hualala...

    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

    $970 to $2,857/night

  7. ESTATE
    Hale Kauka

    Hale Kauka

    Kamuela, 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

    $958 to $1,375/night

  8. VILLA
    Hualalai Resort Fairway Villa 104D

    Hualalai Resort Fairway Villa 104D

    Kailua-Kona, HI

    Upper level 2-bedroom, 2-bath villa overlooking the 15th tee of the Hualalai Golf Course with stunning Mauna Kea, Island of Maui and horizon views of the ocean. Designed by Honolulu-based Architect Warren Sunnland, the Fairway Villas at Hualalai are...

    Pool
    FREE CANCELLATION

    $934 to $2,335/night

  9. CONDOMINIUM
    Whaler at Kaanapali Beach 723

    Whaler at Kaanapali Beach 723

    Lahaina, HI

    Mauka to Makai, translates to: the Mountain to the Ocean, which is the expansive views you have from the wrap around lanai of this two (2) bedroom condo. This open and spacious condo offer sweeping views of Mauna Kahalawai (West Maui Mountains), the...

    Pool
    FREE CANCELLATION

    $895 to $1,231/night

  10. CONDOMINIUM
    Whaler at Kaanapali Beach 1173

    Whaler at Kaanapali Beach 1173

    Lahaina, HI

    Expansive floor plan creates a very spacious two (2) bedroom, two (2) bath condo. This well appointed condo has been completely remodeled with top of the line finishes and furnishings. The lanai wraps around from the mountain side to the center...

    Pool
    FREE CANCELLATION

    $895 to $1,231/night

  11. VILLA
    Bay Villa 22G2 Gold Ocean Front

    Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Perfectly situated above the waves in the most pristine and highly desired locations in Kapalua! This unique floor plan is the only ground-floor Kapalua Bay villas that can boast an additional 150+ square feet of living space facing the ocean!!...

    Pool

    $881 to $1,322/night

  12. HOUSE
    Kainoa

    Kainoa

    Hanalei, HI

    KAINOA:TVNCU-1227: TA#148-488-1920-01 Walk to Hanalei Bay or to Hanalei shops and restaurants This beautifully appointed 4 bedroom, (two master suites) and 3 bath home with Hawaiian and Asian flair. Hardwood floors extend out to the deck in a...

    Hot Tub

    $881 to $1,110/night

  13. CONDOMINIUM
    Hale Lelea Ko Olina Beach Villa (B310)

    Hale Lelea Ko Olina Beach Villa (B310)

    Kapolei, HI

    This vacation home has been registered as a Transient Accommodation with the State of Hawaii – HAWAII TAX ID TA-083-717-4272-01 #groundfloor #view #oceanview #whitewater #group  #wedding #KoOlina #resort #luxury #villa #Kapolei #Oahu #Hawaii...

    Pool Hot Tub

    $856 to $2,016/night

  14. VILLA
    Bay Villa 35B3 Gold Ocean Front

    Bay Villa 35B3 Gold Ocean Front

    Lahaina, HI

    The spacious interior of this 2 bed 3 bath tranquil retreat is the perfect blend of premium comfort and contemporary modern design. Stately and well-appointed, this lovely villa is uniquely positioned for endless views of the Pacific and neighboring...

    Pool

    $847 to $1,322/night

  15. VILLA
    Bay Villa 20G2 Gold Beach Front

    Bay Villa 20G2 Gold Beach Front

    Lahaina, HI

    We invite you to be carried away by this luxury beachfront villa overlooking the azure waters of beautiful Oneloa Bay. Our property is uniquely positioned above the beach in the most desirable location of Kapalua, the crown jewel of West Maui. This...

    Pool

    $847 to $1,322/night

  16. 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

  17. CONDOMINIUM
    Honua Kai-Konea #925

    Honua Kai-Konea #925

    Lahaina, HI

    Unobstructed Ocean Views from our 9th floor 3 bedroom, 3 bath in Konea Tower with over 1610 sq ft of living space at N. Ka'anapali's newest resort-Honua Kai Resort & Spa. Our vacation rental features 2 Master Suites with lanai access from one of the...

    Pool
    FREE CANCELLATION

    $841 to $2,575/night

  18. CONDOMINIUM
    Villa 316

    Villa 316

    Kahuku, HI

    This penthouse villa is located in the most desirable location in the complex, on the third level just steps from the sandy beach with panoramic ocean views and a private serene lanai. This villa is only about 20 yards from the ocean! Photographs...

    Pool Hot Tub

    $808 to $2,609/night

  19. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Direct Ocean Front Cottage where you can watch whales and surfers while relaxing on the large sunning deck, literally hanging over the oceans edge. Features two master suites and private pool, and located just 5 miles from Kailua Village at 78-6658...

    Pool
    FREE CANCELLATION

    $772 to $1,922/night

  20. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Oceanfront estate with breathtaking panoramic unobstructed views. 4 BR, 4 elegant baths. All bedrooms have oceanfront balconies. Walls of glass open to lanai & main living area making this an ideal Hawaiian indoor/outdoor living experience. Elegant...

    Pool Hot Tub

    $766 to $846/night

  21. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This beautiful custom home, built in 2007, boasts 5 buildings totaling interior 3,829 sq. feet; including main house, and a private master suite situated at each of 4 corners. Main house has a private study converted to bedroom with a sink, a half...

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1,540/night

  22. CONDOMINIUM
    Direct Ocean & Beach View 2nd Level 3Bd Villa 203

    Direct Ocean & Beach View 2nd Level 3Bd Villa 203

    Kahuku, HI

    Direct Ocean & Beach View 2nd Level 3Bd (or 4bd w/adjoin studio) Villa 203This villa is located on the second floor in the most desirable location in the complex, just 20 yards from the sandy beach with direct ocean and beach views from just about...

    Pool Hot Tub

    $756 to $2,478/night

  23. CONDOMINIUM
    Beach Level 3 Bed Direct Ocean Views Villa 106 Turtle Bay

    Beach Level 3 Bed Direct Ocean Views Villa 106 Turtle Ba...

    Kahuku, HI

    This beach level villa has beach and ocean views and is located just steps from the sandy beach with a lawn area before the sand starts. The Ocean Villas pool, jaccuzzi and BBQs are all just 20 yards to your right! It has a serene lanai where you...

    Pool Hot Tub

    $756 to $2,478/night

  24. HOUSE
    Honu Ohana House 69-1757

    Honu Ohana House 69-1757

    Waimea, HI

    This is a big, fun beach house with several areas to enjoy as a whole group or to tuck away from the rest of the group’s festivities for some private time. Perfect for multi-generational families and/or extended family with friends. The home is...

    Pool

    $756 to $1,585/night

  25. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Hokulani Villa ~ Simple, Island Luxury Getaway! This newly remodeled Golf Course front home is fresh on the market! This wonderful villa boasts fine furnishings and a very cozy atmosphere. With fantastic views of the golf course, bali hai views and...

    Pool

    $750 to $1,695/night

  26. CONDOMINIUM
    Kaanapali Alii 456

    Kaanapali Alii 456

    Lahaina, HI

    Our Luxury Ocean View condo is PRIVATELY MANAGED. Our condo is not in the Rental Program, so rest assure that our condo photos that you see here, is the one that you will rent from us. The condo unit is located in building 4 on the 5th floor end...

    Pool
    FREE CANCELLATION

    $749 to $1,500/night

  27. 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

  28. CONDOMINIUM
    Makena Surf Resort, #G-201

    Makena Surf Resort, #G-201

    Kihei, HI

    akena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and rocky...

    Pool Hot Tub

    $729 to $1,094/night

  29. CONDOMINIUM
    Makena Surf Resort, #G-104

    Makena Surf Resort, #G-104

    Kihei, HI

    Makena Surf G-104 is a beautiful, ground floor condo that has a spacious lanai complete with its own BBQ. It opens to perfectly manicured grounds where you can enjoy the lawn and incredible views of the pacific ocean. Makena Surf Resort is a...

    Pool

    $729 to $1,094/night

  30. CONDOMINIUM
    Wailea Elua #2204

    Wailea Elua #2204

    Wailea, Maui, HI

    You will immediately sense that the fabulous Maui vacation you have been looking forward to has begun when you step into this completely remodeled 2 bedroom, 2 bath condo located on one of the best locations in the Wailea Elua Village. From our...

    Pool

    $724 to $1,065/night