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
    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

  2. CONDOMINIUM
    Valley Isle #1106

    Valley Isle #1106

    Lahaina, HI

    From the time you open your front door a magnet pulls you across the room directly to the balcony. It takes a few swallows to get that lump cleared from your throat. This is the view you see on the travel channel, travel books, magazines, and post...

    Pool
    FREE CANCELLATION

    $156 to $251/night

  3. CONDOMINIUM
    Sandpiper 121B

    Sandpiper 121B

    Princeville, HI

    Special discount for open August dates! Sandpiper 121B is a perfect choice for couples seeking a romantic getaway on a budget! The private garden-level lanai is surrounded by tropical foliage and flowers. This charming studio has a private bathroom...

    Pool Hot Tub
    FREE CANCELLATION

    $121 to $153/night

  4. CONDOMINIUM
    Sealodge J1

    Sealodge J1

    Princeville, HI

    Sealodge J1: Private, quiet and serene with oceanfront views all the way down the Anini Reef to the Kilauea lighthouse. On the edge of the bluff between the trees and the ocean, this condo sits alone like a separate little house, facing the sea....

    Pool
    FREE CANCELLATION

    $238 to $275/night

  5. CONDOMINIUM
    Puu Poa 310

    Puu Poa 310

    Princeville, HI

    This spacious, upscale Kauai vacation rental offers verdant island beauty along with all of the amenities of home. Relaxation is in abundance inside or out on your lanai (patio). The ocean view master suite has a King size bed, TV/DVD, and private,...

    Pool

    $392 to $542/night

  6. CONDOMINIUM
    Kapalua Golf Villa 25T4 Gold Ocean View

    Kapalua Golf Villa 25T4 Gold Ocean View

    Kapalua, HI

    This lovely Villa has the feeling of casual island elegance with it's open style kitchen and living-dining area. Featuring a luxury gourmet kitchen with quality stainless steel appliances, surrounded by natural stone and warm exotic woods. It...

    Pool

    $294 to $563/night

  7. CONDOMINIUM
    Hale Kalena (Kanaloa 701)

    Hale Kalena (Kanaloa 701)

    Kailua Kona, HI

    Tropical gardens and oceanfront views surround this 1800sqft peaceful 2 bedroom centrally air conditioned condo. With 3 pools facing the ocean, 2 resurfaced tennis courts, and a relaxing BBQ area, this condominium complex provides wonderful...

    Pool Hot Tub

    $204 to $304/night

  8. CONDOMINIUM
    Hale Lau Wai Ko Olina Beach Villa (O704)

    Hale Lau Wai Ko Olina Beach Villa (O704)

    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 CALENDARIf the calendar shows as available, the property can be booked instantly...

    Pool Hot Tub

    $397 to $1,204/night

  9. CONDOMINIUM
    Mahana Resort #1017

    Mahana Resort #1017

    Lahaina, HI

    Outstanding ocean front views on North Ka'anapali beach. Enjoy heavenly sunsets from your living room AND bedroom. This condo has been totally remodeled and is tastefully decorated with an island style theme. The kitchen has granite counter tops and...

    Pool
    FREE CANCELLATION

    $290 to $606/night

  10. CONDOMINIUM
    Lahaina Shores #531

    Lahaina Shores #531

    Lahaina, HI

    5th floor direct ocean front views from our studio unit #531 at the Beach Front Resort: Lahaina Shores. Brand new to our program! Full size kitchen, tiled walk-in shower and a cozy king size bed. Did I mention the views? Breathtaking! Central AC...

    Pool
    FREE CANCELLATION

    $273 to $447/night

  11. CONDOMINIUM
    Lokelani #C205

    Lokelani #C205

    Lahaina, HI

    Remodeled in 2009 complete with updated kitchen appliances, granite and tile throughout. A split A/C system with units in both bedrooms keeps you cool to sleep in the warmer months. Flat screen TV's and DVD players in living room and master bedroom...

    Pool
    FREE CANCELLATION

    $278 to $640/night

  12. CONDOMINIUM
    Papakea #B207

    Papakea #B207

    Lahaina, HI

    Dec 2014 remodel included granite kitchen and bathroom counters tops, new cabinetry, new dishwasher, custom lighting and brand new mattress and Wall bed cabinet. Incredible ocean views overlooking the pool and lush gardens from this studio in North...

    Pool
    FREE CANCELLATION

    $145 to $319/night

  13. CONDOMINIUM
    Kihei Akahi Resort- Unit C313

    Kihei Akahi Resort- Unit C313

    Kihei, HI

    Beautiful garden and partial ocean view upgraded condo. Very comfortable attracts repeat visitors!.This lovely third floor one bedroom, one bath 655 square foot home at the popular Kihei Akahi Resort is renovated, inviting, clean and comfortable....

    FREE CANCELLATION

    $129 to $328/night

  14. CONDOMINIUM
    Paki Maui #109

    Paki Maui #109

    Lahaina, HI

    Ocean front views in our Paki Maui vacation condo in Honokowai, one floor up from ground level. Our Paki Maui condo is remodeled with tile throughout and is tastefully furnished including new furniture package. Enjoy the Visitor's Channel on cable...

    Pool
    FREE CANCELLATION

    $162 to $332/night

  15. CONDOMINIUM
    Kamaole Sands 5-313

    Kamaole Sands 5-313

    Kihei, HI

    Ocean and garden views close to the pool. Enjoy beautiful sunsets every evening from your private lanai in this beautifully updated third floor unit! This one bedroom (plus sleeper sofa), two bath, 818 square foot condo is ideal for families or for...

    Pool Hot Tub
    FREE CANCELLATION

    $136 to $450/night

  16. CONDOMINIUM
    Palms at Wailea #2205

    Palms at Wailea #2205

    Kihei, HI

    We are pleased that our properties at the Palms at Wailea have been chosen to be featured in the number 1 selling book "Maui Revealed" and their website. These properties were chosen because of their superior quality and great rates! The fabulous...

    Pool Hot Tub
    FREE CANCELLATION

    $360 to $741/night

  17. HOUSE
    Maile Hale

    Maile Hale

    Kailua Kona, HI

    Experience a Hawaiian getaway like no other in this private, ocean-view retreat located in the prestigious, gated Keauhou Estates community. Just minutes from the beach, restaurants, shopping, and a variety of island activities, this three-bedroom,...

    $393 to $970/night

  18. CONDOMINIUM
    Keauhou Resort 104

    Keauhou Resort 104

    Kailua Kona, HI

    Relax and rejuvenate in the tranquility of this unique townhouse in Keauhou Resort. Located in a quiet area just south of Kailua-Kona, Keauhou Resort is nestled among a five acre tropical garden. This one bedroom, one bath unit sleeps 3-4 people.The...

    Pool

    $256 to $543/night

  19. CONDOMINIUM
    Kona Plaza 112

    Kona Plaza 112

    Kailua Kona, HI

    Steps to the ocean, shops & restaurants — enjoy life on Alii Drive in Historic Kailua Kona Village! Tropically furnished, this first-floor 2 bedroom / 2 bath retreat is close to elevator and amenities. Throw open the large sliders and the open...

    Pool

    $244 to $577/night

  20. CONDOMINIUM
    Wailea Ekolu #804

    Wailea Ekolu #804

    Wailea, HI

    Wailea Ekolu is one of most sought after properties in Wailea as it is nestled on the Wailea Golf Course. The property has a quiet and private atmosphere as the buildings are spread out across the lush tropical foliage. Wailea Ekolu has two lovely...

    Pool
    FREE CANCELLATION

    $261 to $405/night

  21. CONDOMINIUM
    Maui Vista #2-423

    Maui Vista #2-423

    Kihei, HI

    Maui Vista is a lovely complex located across the street from the famous Kamaole Beach and is 100 yards from Charley Young's Beach. Enjoy miles of sandy beach, snorkeling, surfing and stand-up paddle boarding a short walk away. These beaches have...

    Pool
    FREE CANCELLATION

    $173 to $347/night

  22. CONDOMINIUM
    Kuleana 706 1 Bdrm

    Kuleana 706 1 Bdrm

    Lahaina, HI

    Enjoy the luxury of this beautiful oceanfront condo including all brand new furniture! You will find travertine floors, granite counter tops in the kitchen, an island bar, and bathroom with a custom walk in shower. There is a heavenly King Bed in...

    Pool
    FREE CANCELLATION

    $251 to $461/night

  23. VILLA
    Kapalua Golf Villa 14T

    Kapalua Golf Villa 14T

    Kapalua, HI

    Enchanting one bedroom, two bathroom, luxury Kapalua Golf Villa available for rent starting July 2019. This air conditioned condo, located in the prestigious Kapalua Resort, has been specifically designed for island style relaxation. The main...

    Pool
    FREE CANCELLATION

    $230 to $423/night

  24. CONDOMINIUM
    Lokelani #C104

    Lokelani #C104

    Lahaina, HI

    LOKELANI C-104 was completely remodeled and upgraded October 2015. Features include all new furniture in Hawaiian motif, kitchen with all new appliances, granite counter tops, bathroom with onyx tiled walk in shower with seat, granite counter top...

    Pool
    FREE CANCELLATION

    $191 to $408/night

  25. CONDOMINIUM
    Turtle Bay Alea**NUC 90-TVU-0263

    Turtle Bay Alea**NUC 90-TVU-0263

    Kahuku, HI

    Welcome to Kuilima Estates, the condo property located on the grounds of world-renowned Turtle Bay. The condos are surrounded by two beautifully manicured golf courses, and are the only condos on the North Shore. This is a great place to relax,...

    Pool
    FREE CANCELLATION

    $306 to $341/night

  26. CONDOMINIUM
    Country Club Villas#115

    Country Club Villas#115

    Kailua Kona, HI

    Country Club Villas, Unit#115 is a remarkable NEW addition to the Vacation Rental Market that Knutson & Associates Property Management is proud to represent.Picture yourself living on the "Kona Country Club" golf course, be mesmerized by the...

    Pool Hot Tub
    FREE CANCELLATION

    $241 to $244/night

  27. CONDOMINIUM
    Kona Makai 1-204

    Kona Makai 1-204

    Kailua Kona, HI

    This 2 bedroom 2 bath condo has everything you need to relax in paradise! Enjoy ocean views and gorgeous kona sunsets from your private lanai.The well appointed kitchen is fully equipped to comfortably prepare meals/drinks and the spacious living...

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $363/night

  28. CONDOMINIUM
    Kaanapali Royal #A303

    Kaanapali Royal #A303

    Lahaina, HI

    Kaanapali Royal #A303: Fully remodeled (as of 2015) included tile floors throughout, new furniture, new kitchen with bright and shiny new appliances including washer and dryer. Large lanai features wet bar with sink. Master suite upstairs features a...

    Pool
    FREE CANCELLATION

    $267 to $600/night

  29. CONDOMINIUM
    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    Waikoloa Resort Gem w/ Pool & Hot Tub- Near Beach

    Waikoloa, HI

    ** This home is professionally managed by TurnKey Vacation Rentals, two-time winner of the Travel Weekly Magellan Award for Vacation Rental Hospitality. With TurnKey, you can always expect exceptional service, a high-quality experience, and...

    Pool Hot Tub
    FREE CANCELLATION

    $176 to $304/night

  30. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    TVNCU-1343 - TA# 127-070-6176-01 Hale Ola Kai is a three bedroom, two and a half bath home located near world famous Hanalei Bay. The house is a comfortable family-style home. Casual, yet equipped with anything you need to make your stay in Hanalei...

    FREE CANCELLATION

    $475 to $653/night