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. CONDOMINIUM
    Ocean & Pool View Beachfront 3rd Floor Penthouse Villa 309

    Ocean & Pool View Beachfront 3rd Floor Penthouse Vil...

    Kahuku, HI

    Ocean & Pool View Beachfront 3rd Floor (top) Penthouse Villa 309 This penthouse villa is located on the third level just steps from the sandy beach with beautiful ocean and pool views from the lanai, living room and master bedroom. It has a serene...

    Pool Hot Tub

    $912 to $2,217/night

  2. CONDOMINIUM
    Ocean View and Beachfront Beach Level 3 Bedroom Villa 110

    Ocean View and Beachfront Beach Level 3 Bedroom Villa 11...

    Kahuku, HI

    This beach level villa is located just steps from the pool, BBQs, and the sandy beach! It has partial ocean views from the dining room, kitchen, living room, master bedroom and lanai. It has a serene lanai with Tiki torches lighting the grounds at...

    Pool Hot Tub

    $912 to $2,217/night

  3. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    This stunning Poipu home boasts over 3,300 square feet of elegant living space, along with sweeping views from the coastline up the sloping hills of Kalaheo. An open floor plan provides guests with the perfect setting for quality time together,...

    Pool Hot Tub

    $899 to $2,155/night

  4. 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

  5. HOUSE
    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 Hot Tub
    FREE CANCELLATION

    $895 to $1,231/night

  6. HOUSE
    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 Hot Tub
    FREE CANCELLATION

    $895 to $1,231/night

  7. 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

    $878/night

  8. 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

  9. 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

  10. CONDOMINIUM
    Hale Papakea Ko Olina Beach Villa (B110)

    Hale Papakea Ko Olina Beach Villa (B110)

    Kapolei, HI

    LIVE CALENDAR: If the calendar shows as available, the property IS available and can be booked INSTANTLY online 24/7. This listing and availability are updated in real-time. You can click/tap the calendar tab to see availability. Feel free to...

    Pool Hot Tub

    $856 to $2,016/night

  11. 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

    $856 to $2,016/night

  12. CONDOMINIUM
    Honua Kai- Konea 1019- Penthouse with private BBQ! 3b/3.5b

    Honua Kai- Konea 1019- Penthouse with private BBQ! 3b/3....

    Kaanapali, HI

    *3 Bedroom 3.5 Bathroom*ROYAL PENTHOUSE* 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 Lana'i and Moloka'i, Black Rock...

    Pool Hot Tub

    $853 to $3,320/night

  13. 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

    $845 to $1,668/night

  14. HOUSE
    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 $2,436/night

  15. CONDOMINIUM
    Wailea Elua Unit #1002

    Wailea Elua Unit #1002

    Wailea, HI

    Wailea Elua Village #1002 is in a prime location closest to the ocean, beach and pool. 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...

    Pool

    $841 to $1,515/night

  16. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Island living at its finest! Experience charming plantation style living in this gorgeous Poipu home. Enjoy all the Robert Trent Jones, Jr. community has to offer conveniently located along the Kiahuna Golf Course. Shopping, golf, and beach...

    Pool Hot Tub

    $839 to $1,991/night

  17. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    LIVE CALENDAR: If the calendar shows as available, the property IS available and can be booked INSTANTLY online 24/7. This listing and availability are updated in real-time. Contact us should you have any questions prior to booking. LOCATION: This...

    Pool Hot Tub

    $833 to $2,016/night

  18. CONDOMINIUM
    Honua kai- Luana Garden Villa 3C

    Honua kai- Luana Garden Villa 3C

    Kaanapali, HI

    Luana Garden Villas is the newest offering at the beautiful Honua kai Resort & Spa.  These spacious 3 bedroom Villas are located in 3 private enclaves and include large lanai's, private outdoor kitchens and a private garage. Each Enclave boasts a...

    Pool Hot Tub

    $831 to $2,817/night

  19. VILLA
    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    This 5 star property is perfectly situated above the waves in the most pristine and highly desired locations in Kapalua! Building 22, just steps from the stairs that lead down to the white sands of Oneloa Bay. This unique floor plan is the only...

    Pool

    $813 to $1,219/night

  20. CONDOMINIUM
    Wailea Elua Unit #1204

    Wailea Elua Unit #1204

    Wailea, HI

    Notes from the Owners: Wailea Elua Village #1204 is a beautiful two bedroom, two bath oceanfront condo that has been fully remodeled with top of the line appliances and the latest in furnishings. The large travertine flooring in the kitchen, dining,...

    Pool

    $785 to $1,347/night

  21. VILLA
    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua Bay Villa 21G2 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...

    $781 to $1,219/night

  22. VILLA
    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua, HI

    $500K renovation! New pics on the way!!! Completed March 2019! Highend stainless appliances, newly renovated kitchen and baths, new furnishings throughout; new A/C system! Relax and rejuvenate. The warm tropical breezes and soothing sounds of...

    $781 to $1,219/night

  23. VILLA
    Kapalua Bay Villa 35B3 Gold Ocean Front

    Kapalua 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

    $781 to $1,219/night

  24. VILLA
    Kapalua Bay Villa 34B2 Gold Ocean Front

    Kapalua 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....

    Pool

    $781 to $1,219/night

  25. VILLA
    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua, HI

    Paint to exterior of building scheduled between April 21st and June 15th. This is a rare opportunity to experience this 5 star property for a fraction of the cost!! Contact manager for special rates and details! We invite you to be carried away...

    Pool

    $781 to $1,219/night

  26. 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

    $775 to $1,094/night

  27. CONDOMINIUM
    Makena Surf Resort, #G-101

    Makena Surf Resort, #G-101

    Makena, HI

    A note from the owner. Welcome to our Maui ohana. Our unit is special because of the extra space and privacy, including the cool, shady side lanai we call our grotto - the perfect place to curl up with a good book, and a lovely respite from the...

    Pool

    $775 to $1,094/night

  28. CONDOMINIUM
    Makena Surf Resort Unit #f-212

    Makena Surf Resort Unit #f-212

    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

    $775 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

    $775 to $1,094/night

  30. CONDOMINIUM
    Makena Surf Resort, #B-204

    Makena Surf Resort, #B-204

    Makena, HI

    A note from the owner: Welcome to our piece of paradise. We love time at our Makena Surf unit. Uniquely located on the second floor of B building, we see the spectacular beach and ocean view up-close-and-personal from the privacy of the second...

    Pool

    $773 to $1,319/night