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
    Whaler at Kaanapali Beach 912

    Whaler at Kaanapali Beach 912

    Lahaina, HI

    Completely Remodeled and well-appointed one (1) bedroom, two (2) bath condo. Custom cabinetry, granite counter tops, built-in wine cooler and stainless steel appliances greet you as you walk in. Quality furnishings inspire luxury in this...

    Pool Hot Tub
    FREE CANCELLATION

    $634 to $805/night

  2. VILLA
    Bay Villa 21G4 GOLD Beach Front

    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

  3. 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

  4. HOUSE
    Alii Point- Almost Oceanfront

    Alii Point- 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

  5. 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 $1,336/night

  6. 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
  7. 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

    $583 to $1,294/night

  8. VILLA
    Luxury 3bed/3bath Hideaway

    Luxury 3bed/3bath Hideaway

    Kihei, HI

    Lele Hideaway is a three bedroom, 3 bath two-level condominium suite. Two bedrooms each have a full bathroom and are located on the ground floor. The third bedroom is located below ground level, down a spiral staircase from the living room. The...

    Pool Hot Tub

    $579 to $984/night

  9. CONDOMINIUM
    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 island....

    Pool
    FREE CANCELLATION

    $574 to $899/night

  10. 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

    $572 to $2,016/night

  11. CONDOMINIUM
    B-110: Hale Papakea Ko Olina Beach Villa

    B-110: Hale Papakea Ko Olina Beach Villa

    Kapolei, HI

    One of only two ground floor beachfront 2 bedroom 2 bathroom condos that are closer to the beach than any other Ko'Olina Resort residence. Experience the ultimate oceanfront experience with family and friends. We manage both beachfront units, which...

    Pool Hot Tub

    $572 to $2,016/night

  12. 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 $1,426/night

  13. VILLA
    Bay Villa 22G4 Gold Ocean Front

    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

  14. VILLA
    Bay Villa 17B2 Gold Ocean View

    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. If you have ever dreamed of...

    Pool

    $563 to $1,063/night

  15. VILLA
    Bay Villa 36B3 Gold Ocean Front

    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! A whale watchers dream! This villa offers the best vantage of whales and their young who make the bay their playground during...

    Pool

    $563 to $781/night

  16. VILLA
    Kapalua Bay Villa 29B2

    Kapalua Bay Villa 29B2

    Lahaina, HI

    Kapalua Bay Villa at its best! This oceanfront property was built to enjoy the casual lifestyle of Kapalua. Beautiful views and the sound of the blue pacific greet you from every part of this unbelievable property. This spacious two bedroom, three...

    Pool

    $563 to $1,031/night

  17. 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

  18. HOUSE
    Aniani Hale

    Aniani Hale

    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

    $561 to $900/night

  19. CONDOMINIUM
    Honua Kai Konea 501

    Honua Kai Konea 501

    Kaanapali, HI

    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 gorgeous home has 180 degree views and SUNSETS ALL YEAR LONG. Watch the Whales in...

    Pool Hot Tub

    $556 to $2,071/night

  20. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Hale Ili Ili is an oceanfront gated four-plex in Kihei Maui Hawaii. The property lends itself to a very private and relaxed atmosphere with breathtaking sunsets, sounds of the ocean and rustling palm trees. Many whales, turtles, dolphins and rays...

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  21. 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
  22. CONDOMINIUM
    Kahana Outrigger #2B1

    Kahana Outrigger #2B1

    Lahaina, HI

    This 3 bedroom, 2 bath, 2 story loft style (closed off with windows) unit has its master bedroom and newly remodeled bathroom in the loft with rain shower head in a walk in tiled shower overlooking the living room. Entry, kitchen and dining area all...

    Pool
    FREE CANCELLATION

    $551 to $928/night

  23. CONDOMINIUM
    Maui Kamaole i-214

    Maui Kamaole i-214

    Kihei, HI

    Bright and open two (2) bedroom condo with great Ocean Views at the Maui Kamaole. This condo is located on the second floor and features a loft bedroom. The master bedroom is located on the main floor and has a queen bed and a full bathroom ensuite....

    Pool
    FREE CANCELLATION
  24. HOUSE
    Koa Kai Hale

    Koa Kai Hale

    Princeville, HI

    The ultimate Kauai vacation home, Koa Kai Hale has large windows in every room that surround you with lush north shore views. With 3,300 square feet of living space, this home has plenty of room for everyone to relax into their Hawaiian getaway. Koa...

    $542 to $1,294/night

  25. HOUSE
    Hale Kanani (Kaua'i) TVNC 1342

    Hale Kanani (Kaua'i) TVNC 1342

    Hanalei, HI

    Completely remodeled, this two-bedroom, two-bath home boasts spectacular mountain views, an airy floor plan with high ceilings, beautiful hardwood floors, and new furnishings. Nestled into a quiet cul-de-sac just a short walk from world-renowned...

    $542 to $1,294/night

  26. HOUSE
    Laulea Hale

    Laulea Hale

    Princeville, HI

    The House of Peace and Happiness is the ultimate in Hawaiian comfort and luxury. Perfect vacation home for 2 families. This spectacular home, impeccably clean and beautifully furnished, is situated on a quiet cul-de-sac in one of Princeville's...

    FREE CANCELLATION

    $540 to $1,158/night

  27. HOUSE
    Kealakekua Hale

    Kealakekua Hale

    Captain Cook, HI

    Welcome to Kealakekua Hale, a brand new addition in our Vacation Rental Home Inventory, that we're proud to represent. Are you looking to stay somewhere extremely private, away from the hussle and bussle of downtown, & feel like you're in true...

    FREE CANCELLATION
  28. 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
  29. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Kona Makai 3-302 is a gorgeous top floor, spacious condo that's been recently updated! Great showmanship of pride in property. Nice ocean view. Loft! Essentially a 2 bedroom for the price of 1! The Kona Makai is a beautiful sunny highly sought after...

    Pool Hot Tub
    FREE CANCELLATION
  30. VILLA
    Bay Villa 32B2 Gold Ocean View

    Bay Villa 32B2 Gold Ocean View

    Kapalua, HI

    Lovely Italian Design features new living room and dining room furnishings, magnificent ocean views, 2 master suites and 3 baths. This professionally designed lovely retreat is synonymous with island pleasure. The perfect Rx for all of life's little...

    Pool

    $531 to $969/night