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. 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

    $1,254 to $1,898/night

  2. CONDOMINIUM
    WPH1507 THTC-CTOQ(XS)-STALL-ACH

    WPH1507 THTC-CTOQ(XS)-STALL-ACH

    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
  3. 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

    $1,198 to $2,876/night

  4. 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 $4,186/night

  5. 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 $3,953/night

  6. 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

    $1,179 to $1,664/night

  7. 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 $4,073/night

  8. 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

    $1,150 to $1,605/night

  9. 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

  10. 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

  11. 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 $3,751/night

  12. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    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

    $1,056 to $3,670/night

  13. CONDOMINIUM
    The Montage Kapalua Bay Heliconia 2302

    The Montage Kapalua Bay Heliconia 2302

    Kapalua, HI

    Beautiful 3 bedroom/3.5 bath plus Den Residence. Heliconia Residence at Residences at Montage This beautiful 3 bedroom/3.5 bath plus Den home is situated in Building #2 at the Residences at Montage in beautiful Kapalua. Enjoy the ocean views from...

    Pool

    $1,039 to $5,850/night

  14. 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

  15. 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 $3,345/night

  16. 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

  17. CONDOMINIUM
    Wailea Elua Unit #1403

    Wailea Elua Unit #1403

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $931 to $1,459/night

  18. CONDOMINIUM
    Makena Surf Resort, #G-304

    Makena Surf Resort, #G-304

    Makena, HI

    Makena 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...

    Pool

    $898 to $1,235/night

  19. 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

  20. 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

  21. 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

  22. APARTMENT
    Diamond Head Beach Hotel R2

    Diamond Head Beach Hotel R2

    Honolulu, HI

    One of a Kind 3 Bedroom 2 Bathroom Penthouse on Oahu's Gold Coast Hovering over the ocean, and surrounded by windows, this flat has direct ocean views out of every window. Recently renovated, this full 3 bedroom apartment has a spacious open...

    FREE CANCELLATION
  23. HOUSE
    Hale Grace Aloha

    Hale Grace Aloha

    Kailua Kona, HI

    Searching for vacation rentals with a private pool? Look no further because this is one of the best vacation rentals with a private pool on the Big Island. Nestled in an enclosed tropical garden across the way from the Ali’i outdoor marketplace...

    Pool

    $876 to $1,284/night

  24. 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

    $853 to $3,473/night

  25. CONDOMINIUM
    Makena Surf Resort #B-101

    Makena Surf Resort #B-101

    Makena, Maui, HI

    Makena 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...

    Pool

    $852 to $1,795/night

  26. VILLA
    Bay Villa 21G Gold Beach Front

    Bay Villa 21G Gold Beach Front

    Kapalua, HI

    Stretch out in the spacious comfort of your 2 bedroom 3 bath private villa and take in the warm breezes and magical views that make Kapalua so special. A stately open-air living room provides a full ocean view before opening up to the full panoramic...

    Pool

    $847 to $1,322/night

  27. VILLA
    Bay Villa 30b3 Ocean Front

    Bay Villa 30b3 Ocean Front

    Kapalua, HI

    Relax and rejuvenate. The warm tropical breezes and soothing sounds of the ocean will transport you to a place of total relaxation. Your beautifully UPGRADED KITCHEN with new granite counter tops will beckon you to dine in. After dinner you can curl...

    Pool

    $847 to $1,322/night

  28. 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

  29. VILLA
    Bay Villa 34b2 Gold Ocean Front

    Bay Villa 34b2 Gold Ocean Front

    Kapalua, HI

    Stunning ocean views from every room! Recent upgrades include new furnishings inside and out, new carpet, fresh paint and accessories. The rugged shore below is home to a variety of tropical birds, exotic plants, fish, and giant sea turtles. During...

    Pool

    $847 to $1,322/night

  30. 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