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

    $17,975 to $27,561/night

  2. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Hale Pua (“House of Flowers”) now features AC as an option in all of its sleeping areas: five king bedrooms, one bunkroom with four twin beds and game room with queen sofabed. This special home is maybe the only 6 bed/6 full bath oceanfront...

    Pool

    $2,212 to $3,444/night

  3. 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

  4. 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

  5. CONDOMINIUM
    760 South Kihei Condo Unit 414

    760 South Kihei Condo Unit 414

    Kihei, HI

    Feel Pacific breezes as you unwind on the lanai of your fourth-floor 3BR/2BA condo. This unit commands the most sought-after location in the building (front and center), closest to the ocean and furthest from the road. Take in stunning wide-open...

    Pool
    FREE CANCELLATION

    $607 to $794/night

  6. CONDOMINIUM
    Honua Kai Konea 743

    Honua Kai Konea 743

    Lahaina, HI

    This rarely-available top-floor penthouse condominium is the ultimate in luxury living.  Konea 743 boasts amazing ocean views of Maui and the surrounding islands. This spacious suite includes two bedroom, two full baths and a sofa-bed to...

    Pool Hot Tub
    FREE CANCELLATION

    $577 to $950/night

  7. 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

  8. CONDOMINIUM
    Wai'ula'ula A102 Condominium

    Wai'ula'ula A102 Condominium

    Kamuela, HI

    Your visit to our vacation home will capture the essence of Hawaii. We are located along the Big Island’s exclusive golden Kohala Coast. Play golf on the emerald fairways of the renowned Mauna Kea Resort courses. Experience Kauna’oa and Hapuna,...

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  9. COTTAGE
    Mauna Lani KaMilo Home (424)

    Mauna Lani KaMilo Home (424)

    Kamuela, HI

    This spectacular 3 bedroom- 3 bath single-level cottage is located within Kamilo, which is nestled near the heart of the Mauna Lani Resort area. Upon entering Mauna Lani KaMilo Home (424) enjoy the vaulted ceilings and open floor plan which allows...

    Pool Hot Tub

    $482 to $1,122/night

  10. CONDOMINIUM
    Bali Hai Villas 3 Bedroom

    Bali Hai Villas 3 Bedroom

    Princeville, HI

    Bali Hai Villas If you're looking for a tropical paradise for your vacation, then you have found your destination! Bali Hai Villas offers easy access to Kauai's most popular attractions such as Hanalei Bay, Waimea Canyon State Park, Limahuli Garden...

    Pool Hot Tub
  11. CONDOMINIUM
    Waikiki Beach Walk 4 Bedroom

    Waikiki Beach Walk 4 Bedroom

    Honolulu, HI

    Waikiki Beach Walk The balmy Waikiki Beach Walk is a must see resort. It is located in Honolulu, Hawaii and has 7.7 acres of Waikiki fun and excitement! The beach is easily accessible and you can walk the sandy beach every night before bed for the...

    Pool Hot Tub
  12. CONDOMINIUM
    Kona 2 Bedroom

    Kona 2 Bedroom

    Kailua-Kona, HI

    Kona Aloha! Relax in a true Hawaiian paradise. Welcome to abundant Pacific beach access and topical relaxation, for your group, couples, or family stay. The Kona Coast Resort on Hawaii's Big Island offers a tropical vacation backdrop of Hawaii's...

    Pool Hot Tub
  13. CONDOMINIUM
    Wailea Ekolu 1606

    Wailea Ekolu 1606

    Kihei, HI

    Located in beautiful Wailea, this 2bd 2ba condo is on the top floor and boasts high ceilings and a gorgeous ocean view. Visting with a larger group? We have another unit in the same building! Make sure to ask us the availability for booking 1604...

    Pool
    FREE CANCELLATION

    $350 to $1,593/night

  14. CONDOMINIUM
    Waikoloa Beach Villas D1

    Waikoloa Beach Villas D1

    Waikoloa, HI

    Stay, relax & enjoy in our spacious & comfortable poolside home that has a fully equipped kitchen & 3 bedrooms with luxury linens throughout. Enjoy our DVD library on a 52" HD TV in the family room, or read a book in the separate conversation area....

    Pool
    FREE CANCELLATION

    $345 to $741/night

  15. CONDOMINIUM
    Papakea Unit #K303 Condo

    Papakea Unit #K303 Condo

    Kaanapali, HI

    TOP 10 REASONS TO STAY IN K303 1. View, view, view! The ocean is up close and personal! View of ocean, pool, Island of Molokai and mountains! 2. Air Conditioning throughout the unit- including living room and both bedrooms! NEW FALL 2017 3....

    Pool
    FREE CANCELLATION

    $325 to $619/night

  16. CONDOMINIUM
    Waikiki Beach Walk 2 Bedroom

    Waikiki Beach Walk 2 Bedroom

    Honolulu, HI

    The balmy Waikiki Beach Walk is a must see resort. It is located in Honolulu, Hawaii and has 7.7 acres of Waikiki fun and excitement! The beach is easily accessible and you can walk the sandy beach every night before bed for the pure enjoyment of...

    Pool Hot Tub
  17. CONDOMINIUM
    Kaanapali Royal #B202

    Kaanapali Royal #B202

    Lahaina, HI

    One of the best valued vacation rentals in Kaanapali. The 2 bedroom, 2 bath vacation home, located on the 16th fairway of the Royal Kaanapali Golf Course, is just walking distance to Whaler’s Village and the world famous Kaanapali Beach Resort...

    Pool
    FREE CANCELLATION

    $278 to $600/night

  18. CONDOMINIUM
    760 South Kihei Condo Unit 407

    760 South Kihei Condo Unit 407

    Kihei, HI

    Enjoy sun-soaked beach days and relaxing balmy evenings at this fourth-floor 2BR/2BA Menehune Shores condo. Your rental offers a prime location on the right side of the building, overlooking the pool and ocean. Take a dip in the heated pool, or...

    Pool
    FREE CANCELLATION

    $248 to $554/night

  19. CONDOMINIUM
    Kihei Akahi Resort- Unit B204

    Kihei Akahi Resort- Unit B204

    Kihei, HI

    Second Floor home with Split AC. Large Lanai with Garden Views - Building B. Kihei Akahi Resort B204 - Garden View Two Bedroom Two Bath 879 sq. ft. located on the 2nd floor, in building B. Upgrade - new split AC to keep you cool on warmer days....

    Pool
    FREE CANCELLATION

    $238 to $418/night

  20. APARTMENT
    WS2105 RFRF-CTOQ(RM)-00-ACH

    WS2105 RFRF-CTOQ(RM)-00-ACH

    Honolulu, HI

    Let us welcome you to this Completely Remodeled 1 Bedroom Suite "Majestic Views that will Awe you" in the Waikiki Sunset. World Famous White Sandy Beaches only one block away, Relax and enjoy all the fabulous amenities, Sapphire Blue Tiled Pool,...

    Pool
    FREE CANCELLATION

    $229 to $319/night

  21. CONDOMINIUM
    Waikiki Beach Walk 1 Bedroom

    Waikiki Beach Walk 1 Bedroom

    Honolulu, HI

    The balmy Waikiki Beach Walk is a must see resort. It is located in Honolulu, Hawaii and has 7.7 acres of Waikiki fun and excitement! The beach is easily accessible and you can walk the sandy beach every night before bed for the pure enjoyment of...

    Pool Hot Tub
  22. CONDOMINIUM
    Bali Hai Villas 2 Bedroom

    Bali Hai Villas 2 Bedroom

    Princeville, HI

    Bali Hai Villas If you're looking for a tropical paradise for your vacation, then you have found your destination! Bali Hai Villas offers easy access to Kauai's most popular attractions such as Hanalei Bay, Waimea Canyon State Park, Limahuli Garden...

    Pool Hot Tub
  23. CONDOMINIUM
    Bali Hai Villas 1 Bedroom

    Bali Hai Villas 1 Bedroom

    Princeville, HI

    Bali Hai Villas If you're looking for a tropical paradise for your vacation, then you have found your destination! Bali Hai Villas offers easy access to Kauai's most popular attractions such as Hanalei Bay, Waimea Canyon State Park, Limahuli Garden...

    Pool Hot Tub
  24. CONDOMINIUM
    Maui Vista #1-206

    Maui Vista #1-206

    Kihei, HI

    Maui Vista is a lovely complex located across the street and literally a 3-minute walk from this unit to Charley Young Beach - voted one of the most beautiful beaches in the world. Connected to Charlie Young Beach is the famous Kamaole Beach #1....

    Pool
    FREE CANCELLATION

    $161 to $219/night

  25. CONDOMINIUM
    Studio- Kihei Akahi Condominium- Walk to the Beach & Shops

    Studio- Kihei Akahi Condominium- Walk to the Beach &...

    Kihei, HI

    Enjoy beautiful Maui from this conveniently located studio, which is walking distance to the beach, restaurants and shops! There is 1 free parking space and free Internet. This studio has a Queen Size Murphy Bed, Queen Size Sofa Bed, Full Kitchen,...

    Pool
    FREE CANCELLATION

    $129 to $160/night