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.

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters
  1. CONDOMINIUM
     Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Luxurious Oceanfront Condo on Molokai- Ka Hale Ola

    Kaunakakai, HI

    You will feel so comfortable and "at home" in the condo that you will be reluctant to leave, but there are other wonderful experiences awaiting you on the grounds of Wavecrest. Wander through the lush tropical grounds, enjoy the fabulous pool right...

    Pool
    FREE CANCELLATION

    $158 to $191/night

  2. HOUSE
    Hale Lokahi

    Hale Lokahi

    Waialua, HI

    Hale Lokahi - House of Peace and Serenity - This home is located in one of the best kept, secret neighborhoods on the north shore. Right on a white sand beach, this family-owned house is perfect for your vacation in paradise.. This 4 bedroom, 2...

    FREE CANCELLATION

    $683 to $992/night

  3. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, 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

  4. CONDOMINIUM
    Kaanapali Shores 819

    Kaanapali Shores 819

    LAHAINA, HI

    This beautiful 1-bedroom, 1-bathroom oceanfront condominium provides everything you need for your vacation in paradise. With spectacular views of the ocean from the 8th floor and a spanning view of the beautiful resort, you can’t beat the view...

    Pool Hot Tub
    FREE CANCELLATION

    $206 to $406/night

  5. CONDOMINIUM
    Kihei Beach Unit #603

    Kihei Beach Unit #603

    Kihei, HI

    A note from the owner: Unit 603 is a Top Floor Waterfront suite with additional spacious terraces to enjoy the breathtaking ocean and beach views. The suite is a beautifully updated Open Plan, with sandstone flooring, granite counters and fully...

    Pool

    $223 to $309/night

  6. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    This vintage Hawaiian beach house is nestled in a private gated community of Kona Bay Estates. The simple seaside style will melt all of your cares away as you sip on your Mai Tai in the cool shade of the deep, covered lanai. Experience the feel of...

    Pool
    FREE CANCELLATION

    $525 to $555/night

  7. CONDOMINIUM
    Kauhale Makai #330

    Kauhale Makai #330

    Kihei, HI

    Hawaiian for "Village By The Sea," the Kauhale Makai complex is an oceanfront property located in Kihei. This is one of a few buildings in the area with central air conditioning - not window units. This condo stays as cool as you like it. Kihei is...

    Pool Hot Tub
    FREE CANCELLATION

    $161 to $266/night

  8. CONDOMINIUM
    Hale Pumehana Ko Olina Beach Villa (O1202)

    Hale Pumehana Ko Olina Beach Villa (O1202)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. L I V E C A L E N D A R If the calendar shows as available, the Villa is not reserved...

    Pool Hot Tub

    $740 to $1,668/night

  9. CONDOMINIUM
    Lil Grass Shack-103

    Lil Grass Shack-103

    Lahaina, HI

    Book today and Fall in LOVE with "THE LIL GRASS SHACK" You will feel like you have gone back in time to the true Hawaiian experience in this condo, just 10 FT from the water's edge! 103 Pohailani Welcomes you with so much Included in our...

    FREE CANCELLATION

    $187 to $239/night

  10. CONDOMINIUM
    C5-1 Bedroom Oceanfront

    C5-1 Bedroom Oceanfront

    Kihei, HI

    Ma'alaea Surf, Unit C5, is a conveniently located ground floor unit, just steps away from the small pool. This luxurious unit features a fully furnished kitchen, large living room and a large master suite with a king bed. Enjoy the ocean views and...

    Pool
    FREE CANCELLATION

    $259 to $428/night

  11. CONDOMINIUM
    G4-1 Bedroom Oceanfront

    G4-1 Bedroom Oceanfront

    Kihei, HI

    Ma'alaea Surf, Unit G4 is a conveniently located ground floor unit, just steps away from the large pool. This warm luxurious unit features a recently upgraded fully furnished kitchen, large master suite with King size bed and a queen size sofa bed...

    Pool
    FREE CANCELLATION

    $259 to $428/night

  12. CONDOMINIUM
    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit A2 is a conveniently located ground floor condo, just steps from the beach. This luxurious unit features a full kitchen and dining table. The master bedroom has a king sized bed. The large living room has expansive views and a...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  13. CONDOMINIUM
    H4-2 Bedroom Beachfront

    H4-2 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit H4 is deluxe in every sense. H4 is an ideally located ground floor unit, approximately 5 steps from the white sandy beach. This exceptional unit features a full kitchen, second bedroom and bath. Enjoy the ocean views and Maui's...

    Pool
    FREE CANCELLATION

    $416 to $664/night

  14. CONDOMINIUM
    F5-2 Bedroom Oceanfront Townhouse

    F5-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Ma'alaea Surf, Unit F5 is a townhouse unit situated on the second floor offering guest total privacy. With the latest in contemporary upgrades, this gorgeous unit features a fully furnished modern kitchen and the convenience of a second bedroom and...

    Pool
    FREE CANCELLATION

    $343 to $540/night

  15. CONDOMINIUM
    G10-2 Bedroom Oceanfront Townhouse

    G10-2 Bedroom Oceanfront Townhouse

    Kihei, HI

    Ma'alaea Surf, Unit G10 is a two story townhouse unit with vaulted ceilings. Situated on the second floor this unit has a very open feel and offers our guest total privacy. This unit has a large lanai, stunning ocean views and overlooks the large...

    Pool
    FREE CANCELLATION

    $343 to $540/night

  16. CONDOMINIUM
    D5-1 Bedroom Beachfront

    D5-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit D5 - Newly renovated, and perfectly located, D5 is a ground floor unit, approximately 5 steps from the white sandy beach. This stylish unit features a new kitchen with top grade electrical appliances. Enjoy the large master suite...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  17. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Beautifully appointed "like new" 2 bedroom 2.5 bath oceanfront home with pool. Gourmet kitchen and huge deck for tanning, dining & sunset cocktails. Upstairs master has shower & hot tub. Sliding doors disappear into walls for the ultimate "on the...

    Pool

    $486 to $608/night

  18. CONDOMINIUM
    New! Updated! Modern, Maui Beachfront with Central A/C

    New! Updated! Modern, Maui Beachfront with Central A/C

    Lahaina, HI

    Most frequently asked questions re: payments, cancellations, our home, and the area, can be answered in the property info, guest reviews, and pictures, below. We kindly ask that you read all of these details, as we offer a lot of amenities that...

    Pool Hot Tub
    FREE CANCELLATION

    $561 to $731/night

  19. CONDOMINIUM
    Kihei Beach Unit #606

    Kihei Beach Unit #606

    Kihei, HI

    Kihei Beach is a moderately sized six story beachfront property located in North Kihei. It offers sweeping views of Kahoolawe, Molokini and the dazzling Pacific Ocean and a friendly casual atmosphere. Fronting the property is Sugar Beach, well known...

    Pool

    $241 to $326/night

  20. VILLA
    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua Bay Villa 32B3 Gold Ocean View

    Kapalua, HI

    Spectacular views of the Pacific and the neighboring island of Molokai. Magnificent painted sky at dusk and dawn will take your breath away! Perfectly positioned to allow warm tropical breezes and gentle sounds of surf fill every room. This...

    Pool

    $369 to $594/night

  21. 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

  22. VILLA
    Kapalua Bay Villa 11B3-4 Gold Ocean View

    Kapalua Bay Villa 11B3-4 Gold Ocean View

    Kapalua, HI

    This beautiful and peaceful retreat offers two spacious master suites and three baths all on the top floor with ocean views as far as the eye can see. Centrally located in the resort and walking distance to four world class beaches, two...

    Pool

    $406 to $781/night

  23. CONDOMINIUM
    Pali Ke Kua 115

    Pali Ke Kua 115

    Princeville, HI

    Feel at home in Paradise in this one bedroom condominium at Pali Ke Kua. Enjoy extraordinary views of the ocean or stroll down to Pali Ke Kua's secret beach via a private, paved path. This condo is perfect for a couple's retreat. Rates may vary –...

    Pool Hot Tub

    $259 to $301/night

  24. CONDOMINIUM
    Noelani # 115

    Noelani # 115

    Lahaina, HI

    Not one, but two oceanfront pools and a Jacuzzi, what more can you ask for? Unit 115 is a ground floor unit with washer and dryer and air conditioning. You'll love just walking out from your private lanai right into the swimming pool. Turtles...

    Pool Hot Tub
    FREE CANCELLATION

    $228 to $313/night

  25. CONDOMINIUM
    Pohailani #223

    Pohailani #223

    Lahaina, HI

    Guests are sure to enjoy a memorable family vacation in this fully furnished, 2 bedroom/1 bath condo. The main bedroom has a queen sized bed, while the other bedroom is furnished with 2 Twins. It is perfect for a family as it can sleep 4 people....

    Pool
    FREE CANCELLATION

    $183 to $353/night

  26. HOUSE
    Junior Suite Oceanfront #1007

    Junior Suite Oceanfront #1007

    Lahaina, HI

    Our Junior Suite on the TENTH Floor is spacious and well-appointed with a King Bed as well as a sofa bed for the occasional guest. You will find seating arrangements for relaxing and dining. There is plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  27. HOUSE
    2 Bedrooms Oceanfront

    2 Bedrooms Oceanfront

    Lahaina, HI

    This premium oceanfront Two Bedroom, Two Bath condo is conveniently located on the ground level. Master Bedroom has a King Bed with a private bathroom. Second Bedroom has a queen bed; and the living room has a queen sofa bed for the extra guests....

    Pool Hot Tub
    FREE CANCELLATION

    $516 to $620/night

  28. HOUSE
    Junior Suite Oceanfront #906

    Junior Suite Oceanfront #906

    Kaanapali, HI

    Our Junior Suite is spacious and well-appointed with a Queen Bed and seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and personal items. The kitchen comes fully equipped with all the modern...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  29. HOUSE
    Junior Suite Oceanfront #403

    Junior Suite Oceanfront #403

    Lahaina, HI

    Lovely Oceanfront Junior Suite that features one large room with fully equipped kitchen and bath. Queen-size bed (Sleeps 2). Can accommodate 3 people with added roll-away. Located on the shores of Ka‘anapali Beach in West Maui, Maui Kai is an...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  30. CONDOMINIUM
    Wailea Elua Unit #0302

    Wailea Elua Unit #0302

    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

    $448 to $823/night