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

    Indulge yourself in the ultimate island style luxury at the Big Island of Hawaii’s most exclusive retreat, Kauhale Pilialoha. Experience breathtaking sunsets, enjoy the natural beauty of Hawaii from the ultimate poolside lanai perched on the...

    Pool Hot Tub

    $17,975 to $27,561/night

  2. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Hapuna Beach house description Welcome to Kalina at the High Bluffs of Mauna Kea Located on Kohala Coast on the Big Island of Hawaii, this luxurious private home is just a short golf cart ride away from the premier Mauna Kea Golf Course. It is...

    Pool Hot Tub

    $4,524 to $4,955/night

  3. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, 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

    $1,168 to $2,876/night

  4. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    MAUNA LANI TERRACE#D-201 Beachfront Location, Breathtaking Views, BEST VALUE!!!! AMAZING NEW PROPERTY BOOKING SPECIALS FOR LAST MINUTE VACANCIES!! Call/Text Blake Kessner, Property Manager at or email for any questions at all!! To get the...

    Pool Hot Tub
    FREE CANCELLATION

    $725 to $759/night

  5. HOUSE
    Keauhou Elima

    Keauhou Elima

    Kailua Kona, HI

    What is better than a Hawaiian sunset over the ocean? A sunset over the ocean that you can take in from the privacy of your tropical home-away-from-home! With nearly 5,000 square feet of indoor/outdoor living space, including a lanai with a pool...

    Pool

    $689 to $1,678/night

  6. CONDOMINIUM
    Oceanfront 3BR w/ Private Beach & AC

    Oceanfront 3BR w/ Private Beach & AC

    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

    $577 to $794/night

  7. VILLA
    Kapalua Bay Villa 29B2 Ocean Front

    Kapalua Bay Villa 29B2 Ocean Front

    Lahaina, HI

    Kapalua Bay Villa at its best! This oceanfront property represents the best of Kapalua! Currently undergoing a beautiful renovation. New pics on the way! The owner spares no expense in this high end renovation Exotic Acacia Wood floors and a...

    Pool

    $563 to $1,031/night

  8. 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

  9. CONDOMINIUM
    Hanalei Bay Resort 52012

    Hanalei Bay Resort 52012

    Princeville, HI

    World class resort on world class beach! Beautiful tropical Hanalei Bay resort has convenient access to the beach via a paved path. Its 20 acres include eight tennis courts, two swimming pools one with tropical waterfall and a children's beach, a...

    Pool Hot Tub
    FREE CANCELLATION

    $520 to $581/night

  10. CONDOMINIUM
    Hanalei Colony Resort I1

    Hanalei Colony Resort I1

    Hanalei, HI

    **Please note that the Waipa Bridge will be closed from 9pm on July 12th through 5am on July 15th. Your only option to access Hanalei Colony Resort on those days will be via shuttle. You may leave your car overnight at the Waipa Park and Ride and...

    Pool
    FREE CANCELLATION

    $488 to $581/night

  11. CONDOMINIUM
    Hanalei Colony Resort E3

    Hanalei Colony Resort E3

    Hanalei, HI

    Wow, you'll have this fabulous north shore beach all to yourselves!!! July 1 marks the date our Hanalei Colony Resort rentals re-open to guests - and for a limited time we'll have a special rate available. For a year now, the North Shore past...

    Pool
    FREE CANCELLATION

    $488 to $581/night

  12. HOUSE
    Ocean Tree House w/ Lanai & Yard- Walk to Beach

    Ocean Tree House w/ Lanai & Yard- Walk to Beach

    Kailua, HI

    Located in the upscale neighborhood of Lanikai, this 3BR/2BA is affectionately named Ocean Tree House and is within strolling distance to Lanikai Beach — regarded as one of the world's most beautiful top beaches, with its flour-soft white sands,...

    FREE CANCELLATION

    $485 to $803/night

  13. CONDOMINIUM
    Hale Malu Ko Olina Beach Villa (O221)

    Hale Malu Ko Olina Beach Villa (O221)

    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. LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $485 to $1,204/night

  14. HOUSE
    Ainamalu 29 at Waikoloa Beach Resort

    Ainamalu 29 at Waikoloa Beach Resort

    Waikoloa, HI

    Come and enjoy a luxurious laid-back island living in our new home located in the beautiful new neighborhood in Waikoloa Beach Resort – Ainamalu. This gated community Ainamalu "Protected, Peaceful Land" is the newest resort community in the...

    FREE CANCELLATION

    $481 to $896/night

  15. HOUSE
    Hawaii Kai 4BR w/ Wraparound Lanai & Ocean Views

    Hawaii Kai 4BR w/ Wraparound Lanai & Ocean Views

    Honolulu, HI

    Prepare to be wowed by unforgettable views at this 4BR/3BA home, ideally situated in Honolulu’s beautiful Hawaii Kai.Overlooking Maunalua Bay, Koko Marina, and Hawaii Kai, you’ll enjoy sweeping ocean and Koko Head vistas from almost every room...

    FREE CANCELLATION

    $478 to $890/night

  16. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-104

    Keauhou Kona Surf & Racquet Club #5-104

    Kailua Kona, HI

    Keauhou Kona Surf & Racquet Club#5-104 DIRECT OCEANFRONT, BEST GROUND FLOOR CORNER! REMODELED! AMAZING PROPERTY AIR CONDITIONING INSTALLED AS OF NOVEMBER 2017!! BRAND NEW SPLIT AC UNITS INSTALLED IN LIVING ROOM, & BOTH BEDROOMS!! RARE & PHENOMENAL...

    Pool
    FREE CANCELLATION

    $453 to $467/night

  17. CONDOMINIUM
    Wai'ula'ula D201

    Wai'ula'ula D201

    Kamuela, HI

    Welcome to Wai'ula'ula at the Mauna Kea Resort! Your vacation will truly be one to remember in this beautifully decorated condominium in the gated community of Wai'ula'ula, located on the Hapuna Golf Course. This recently built luxury development...

    Pool Hot Tub
    FREE CANCELLATION

    $444 to $1,174/night

  18. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Welcome to Wai'ula'ula at the Mauna Kea Resort! Your vacation will truly be one to remember in this beautifully decorated condominium in the gated community of Wai'ula'ula is located on the Hapuna Golf Course. This recently built luxury development...

    Pool Hot Tub
    FREE CANCELLATION

    $444 to $1,205/night

  19. CONDOMINIUM
    Sugar Beach Resort PH 14

    Sugar Beach Resort PH 14

    Kihei, HI

    The Sugar Beach Resort is the perfect destination for your tropical Hawaiian getaway! This oceanfront complex is just a few steps away from Maui's longest continual white sand beach, perfect for long strolls on the beach or enjoying postcard...

    Pool Hot Tub
    FREE CANCELLATION

    $428 to $579/night

  20. CONDOMINIUM
    Palms at Wailea #1503

    Palms at Wailea #1503

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long white sandy shoreline. The Palms at Wailea is a gorgeous property; lush with tropical landscaping....

    Pool Hot Tub
    FREE CANCELLATION

    $418 to $585/night

  21. CONDOMINIUM
    Puu Poa 405

    Puu Poa 405

    Princeville, HI

    This spacious top floor condo in the upscale Puu Poa complex on the north shore of beautiful Kauai is located directly next door to the Princeville St Regis Hotel. You'll love the newly renovated oceanfront pool! Also available onsite are tennis...

    Pool
    FREE CANCELLATION

    $397 to $458/night

  22. CONDOMINIUM
    Sugar Beach Resort PH 40

    Sugar Beach Resort PH 40

    Kihei, HI

    The Sugar Beach Resort is the perfect destination for your tropical Hawaiian getaway! This oceanfront complex is just a few steps away from Maui's longest continual white sand beach, perfect for long strolls on the beach or enjoying postcard...

    Pool Hot Tub
    FREE CANCELLATION

    $393 to $544/night

  23. HOUSE
    Tranquil 4BR Home by Private Beach

    Tranquil 4BR Home by Private Beach

    Kahuku, HI

    Your charming 4BR/2BA home is just a short walk from a hidden Kahuku beach. From the updated granite kitchen to the spacious back deck and yard, this tranquil retreat offers seamless indoor and outdoor living, plus extras like boogie boards and...

    FREE CANCELLATION

    $383 to $599/night

  24. CONDOMINIUM
    Hale Maluhia Ko Olina Beach Villa (O425)

    Hale Maluhia Ko Olina Beach Villa (O425)

    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. LIVE CALENDAR If the calendar shows as available, the property is not reserved and can...

    Pool Hot Tub

    $374 to $1,204/night

  25. CONDOMINIUM
    Hanalei Bay Resort 5202

    Hanalei Bay Resort 5202

    Princeville, HI

    World class resort on world class beach! Hanalei Bay Resort is situated on over 20 tropical acres with ocean and sunset views of both Hanalei Bay and world famous Bali Hai mountain, plus boasts a gorgeous sandy beach fronting the property. A paved...

    Pool Hot Tub
    FREE CANCELLATION

    $373 to $410/night

  26. CONDOMINIUM
    Hale Kaimana

    Hale Kaimana

    Kamuela, HI

    Mauna Kea condo description Rare 3BR * Sleeps 6 * Panoramic Ocean Views * On 4th Fairway * Amenity Cards Available with fee*  Kumulani G-1, our 3-bedroom, 2-bathroom condominium home in the world-famous Mauna Kea Resort, has an Ocean view and...

    Pool Hot Tub

    $342 to $646/night

  27. VILLA
    Waikoloa Beach Villas I1

    Waikoloa Beach Villas I1

    Waikoloa, HI

    Waikoloa Beach Villa I1 is sprawled out over 2,200 square feet and features three bedrooms, three full bathrooms and comfortably accommodates up to eight guests. From the front porch, guests enter the home where there is a warm and inviting living...

    Pool Hot Tub
    FREE CANCELLATION

    $333 to $741/night

  28. CONDOMINIUM
    Waikoloa Beach Villas O4

    Waikoloa Beach Villas O4

    Waikoloa, HI

    Aloha and Welcome to our 3 bedroom, 3 bath townhome located in Waikoloa Beach Villas. Discover the beauty of the Island of Hawaii and all it has to offer. Waikoloa Beach Villas is conveniently located 25 minutes from the airport in Kona. Close to...

    Pool
    FREE CANCELLATION

    $333 to $703/night

  29. CONDOMINIUM
    Big Island Paradise

    Big Island Paradise

    Waikoloa, HI

    Sprawling, Exclusive Hali’i Kai Condo 22F Imagine this: You wake up to balmy Hawaiian breeze and wander onto your bedrooms personal lanai to watch the morning sun on the mountains. After a hike along the lava-rock seashore, you take a dip in the...

    Pool Hot Tub

    $330 to $689/night

  30. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    Kamaole Beach III is just across the street from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property and tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night