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 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    The name 'Kapa' 'lua' means above waters edge. This ocean front beauty is uniquely perched above the waters edge along the most desirable stretch of Maui coastline just steps from the sand. Quiet coves make for excellent snorkeling and swimming,...

    Pool

    $625 to $844/night

  2. VILLA
    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua, HI

    Located in the most desirable area of the resort, (building 21), this beach front 1 bed 1.5 bath villa is just steps from the white sand beach of Oneloa Bay, and a short walk to Kapalua Bay, this little jewel offers expansive ocean views from every...

    Pool

    $625 to $844/night

  3. CONDOMINIUM
    Hale Makai Ko Olina Beach Villa (O805)

    Hale Makai Ko Olina Beach Villa (O805)

    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

    $624 to $1,668/night

  4. CONDOMINIUM
    B-903 Beach Villa

    B-903 Beach Villa

    Kapolei, HI

    Beachfront Living at its finest! This 3 bedroom, 3 bath Villa is located in the beautiful Ko Olina Resort on the quiet West side of Oahu. The Beach Villas are the newest, and only, beachfront condominiums available on the island in 25 years....

    Pool

    $624 to $1,784/night

  5. CONDOMINIUM
    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2b

    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2...

    Kaanapali, HI

    Absolutely the MOST DESIRABLE 2 bedroom 2.5 bath condo in the entire complex. Konea 501 is the top unit of only 5 TWO BEDROOM ALI'I SUITES with DIRECT OCEAN VIEWS and private OUTDOOR KITCHENS. At 1620 sq ft with a HUGE 415 sq ft lanai this...

    Pool Hot Tub

    $614 to $2,126/night

  6. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Wailea Elua is the premier ocean front property in Wailea. A gated property situated right on picturesque Ulua Beach, it has one of the best locations in Wailea. There are miles of spectacular walking paths that follow the ocean. In addition, the...

    Pool Hot Tub
    FREE CANCELLATION

    $609 to $1,073/night

  7. HOUSE
    Alii Point #15- Almost Oceanfront

    Alii Point #15- Almost Oceanfront

    Kailua Kona, HI

    Almost Oceanfront. Spend your vacation in a luxurious single family home within a private, gated, enclave of 16 seaside homes. This Alii Point subdivision of fine, luxury residences is a tropical paradise surrounded by a botanical garden with beach...

    Pool

    $608 to $791/night

  8. HOUSE
    Kiahuna Lani at Poipu

    Kiahuna Lani at Poipu

    Koloa, HI

    Experience a slice of heaven at Kiahuna Lani at Poipu. This beautiful 3 bed 3 bath home features privacy and comfort nestled within the exclusive Wainani community on Kauai's scenic and sunny South Shore. Enjoy the 1942 square foot spacious open...

    Pool Hot Tub

    $601 to $1,137/night

  9. HOUSE
    Hale Anu Keanu

    Hale Anu Keanu

    Princeville, HI

    With an ideal location, plenty of privacy, and a backyard jacuzzi, this newly remodeled, plantation-style vacation home on Kauai's north shore allows you to experience the perfect balance of relaxation and adventure. Meaning “house of cool...

    Hot Tub

    $595 to $1,342/night

  10. HOUSE
    Leilani Kai Hale

    Leilani Kai Hale

    Princeville, HI

    Panoramic mountain views and tropical vegetation surround you in this beautifully updated Princeville luxury home with air conditioning and its own saltwater pool and spa. Complete with stylish furnishings and fine finishes such as granite counter...

    Pool Hot Tub

    $595 to $1,283/night

  11. VILLA
    Kapalua Bay Villa 28B2 Gold Ocean Front

    Kapalua Bay Villa 28B2 Gold Ocean Front

    Lahaina, HI

    E Komo Mai 'Welcome' to Aloha Vacation Villa’s newest WATERFRONT vacation property! Nestled in the luxurious Kapalua area in north Maui, the spacious interior of this 2 bed 3 bath tranquil retreat is the perfect blend of premium comfort and...

    Pool

    $594 to $1,063/night

  12. VILLA
    Kapalua Bay Villa 12B2 Gold Ocean View

    Kapalua Bay Villa 12B2 Gold Ocean View

    Lahaina, HI

    Wake up every morning to ocean breezes and spectacular 180° panoramic views of the Pacific Ocean, neighboring islands, and Maui’s north shore coast line. Within easy walking distance to beaches and coastal walking trails. Newly remodeled by an...

    Pool

    $594 to $1,063/night

  13. HOUSE
    Kahana Reef #322

    Kahana Reef #322

    LAHAINA, HI

    **Kahana Reef will be undergoing construction to the Seawall, beginning June 2019. Please be advised that there is construction taking place on the property.** Ocean Front Studio with gorgeous ocean views and views of the island of Molokai. This...

    Pool
    FREE CANCELLATION

    $593 to $1,185/night

  14. HOUSE
    Mahuahua Hale

    Mahuahua Hale

    Kailua Kona, HI

    This 2700+ square ft. house is perfect for entertaining family and friends! With so much space you can accommodate everyone's needs; whether that be barbecuing down by the pool with friends or finding a quiet, private spot to relax with a favorite...

    Pool
    FREE CANCELLATION

    $584/night

  15. HOUSE
    Kahana Outrigger #1A2

    Kahana Outrigger #1A2

    Lahaina, HI

    Four words describe our Condo in paradise… A SLICE OF HEAVEN! With three bedrooms, each with their own full bathroom, our spacious 1450 square foot Condo is more like a cottage or bungalow than the typical condo/hotel room you find on the...

    Pool
    FREE CANCELLATION

    $574 to $986/night

  16. HOUSE
    Ohana Kamalani

    Ohana Kamalani

    Princeville, HI

    Situated in the heart of Princeville on the renowned Makai Golf Course, this luxury vacation rental with Bali Hai and ocean views offers ample space to comfortably accommodate eight guests. Complete with a private pool and air conditioning...

    Pool

    $571 to $1,414/night

  17. HOUSE
    Hoku'Ea Hale

    Hoku'Ea Hale

    Kailua Kona, HI

    All Rooms open to the ocean to fully enjoy spectacular oceanfront living in the Kahalu’u Bay. Enter the beautiful Hoku' Ea Hale named for the beautiful turtle gate that provides complete privacy from the outside. You will immediately be drawn to...

    Hot Tub

    $566 to $846/night

  18. HOUSE
    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    Kailua Kona, HI

    Known as ‘Aniani Hale,’ or Glass House, this stunning 4BR/4.5BA home is situated just above the heart of Kailua-Kona. Elevated 700 feet above sea level, your beautiful island getaway boasts refreshing trade winds from the west and mountain...

    Pool Hot Tub
    FREE CANCELLATION

    $565 to $826/night

  19. VILLA
    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua Bay Villa 30G4 Ocean Front

    Kapalua, HI

    Treat your senses to the majestic ocean views, the musical sound of a variety of exotic birds, the sweet scent of plumeria that fills the air around you and feel the sense of complete relaxation as the warm tropical breezes carress you and transport...

    Pool

    $563 to $969/night

  20. VILLA
    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua Bay Villa 36B3 Gold Ocean Front

    Kapalua, HI

    This elegant and upscale villa occupies the top two floors and features rare West-facing views for magnificent sunsets and 180* ocean views from your master suite! A whale watchers dream! This villa offers the best vantage of whales and their...

    Pool

    $563 to $781/night

  21. VILLA
    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua Bay Villa 22G4 Gold Ocean Front

    Kapalua, HI

    Dreaming of Paradise? You'll pinch yourself when you walk into this gorgeous Bay Villa. It's everything you imagined and more, including discounts on tee times at the world-famous Plantation and Bay Courses. Start your vacation with a frosty...

    Pool

    $563 to $781/night

  22. VILLA
    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua Bay Villa 17B2 Gold Ocean View

    Kapalua, HI

    Over $600K in recent upgrades! Even the best photos can not capture the true beauty of the high-end materials used, the designer furniture and accessories and the magnificent views that surround this 5 star property. Wrap yourself in the luxury of...

    Pool

    $563 to $1,063/night

  23. 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

  24. VILLA
    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua Bay Villa 23B3 Ocean Front

    Kapalua, HI

    This unique oceanfront villa is a whale watchers dream! Ocean views span the entire coastline! Uniquely positioned to include sunset views and situated on one of the most beautiful stretches of coastline in Maui. You will be captivated by the...

    Pool

    $563 to $969/night

  25. 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

  26. CONDOMINIUM
    Mahana 701

    Mahana 701

    Lahaina, HI

    Beautiful 7th floor 2br/2ba condominium at The Mahana at Kaanapali provides everything you need for your vacation in paradise. Equipped with granite counter tops, beautiful tile floors, central A/C, WiFi, flat screen TV, stocked kitchen, and...

    Pool Hot Tub
    FREE CANCELLATION

    $561 to $1,665/night

  27. CONDOMINIUM
    Royal Mauian Unit #102

    Royal Mauian Unit #102

    Maui, HI

    A note from the owner: This unit has been remodeled and has central air conditioning, LCD flat screen TVs, luxury linens, kitchen supplies, and more. Walk out directly to Kamaole Beach Park 1. Snorkeling is great right in front of the property....

    Pool

    $560 to $702/night

  28. CONDOMINIUM
    Royal Mauian Unit #302

    Royal Mauian Unit #302

    Kihei, HI

    Royal Mauian is a unique six story oceanfront property located in South Kihei offering unobstructed views of the clear blue Pacific. The property and adjacent Kamaole Beach together provide excellent locations for stunning sunsets, snorkeling,...

    Pool

    $560 to $702/night

  29. CONDOMINIUM
    Menehune Shores Unit #510

    Menehune Shores Unit #510

    Maui, HI

    This unit was completely remodeled in 2013 with beautiful cabinets of carbonized bamboo (completely renewable, sustainable and simply gorgeous), yellow cedar ceilings, planking tile flooring, granite counter-tops, specialty bathroom fixtures (think...

    Pool

    $560 to $662/night

  30. CONDOMINIUM
    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Kaanapali, HI

    Honua Kai Hokulani 709 is clearly the best 2 bedroom condo available in the Hokulani Building. Top of the highly desirable "09" stack, it just doesn't get any better than this. The best Ocean views from INSIDE the condo from this top floor home....

    Pool Hot Tub

    $556 to $2,038/night