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
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    Experience beach living in this beautiful vacation home on Puako Beach. This private residence is located right across the street from the ocean. Great place to kayak and snorkel in one of the best snorkeling spots on the Big Island. Or bask with...

    FREE CANCELLATION

    $485 to $652/night

  2. CONDOMINIUM
    Puako Beach Condo 109

    Puako Beach Condo 109

    Waimea, HI

    This Puako Beach Condo is one of the nicest remodels in the building. Granite floors throughout! Brand new furnishings, new appliances, whirl pool tub, nice flat screen TVs in 3 of the rooms. The living room TV is web enabled, plus a web enabled...

    Pool
    FREE CANCELLATION

    $235 to $367/night

  3. CONDOMINIUM
    Hale Ohana Aloha

    Hale Ohana Aloha

    Waikoloa, HI

    Big Island dreams begin at Hali'i Kai 7D, an ocean-view vacation condominium at renowned Waikoloa Beach Resort. Ideal for group getaways of up to six people, this 2-bedroom, 2-bath condo features an updated interior, access to impeccable resort...

    Pool Hot Tub

    $286 to $478/night

  4. VILLA
    Waikoloa Beach Villas P32

    Waikoloa Beach Villas P32

    Waikoloa, HI

    We have traveled from our island home in Honolulu numerous times over the years to explore the Big Island. The Big Island offers a diversity of amazing sights including a huge selection of beautiful sunny beaches, snow-capped Mauna Kea, and an...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $407/night

  5. CONDOMINIUM
    Kaanapali Royal N102

    Kaanapali Royal N102

    Lahaina, HI

    Situated on top of the hill by the 16th Tee, the location of our ground floor condo offers the best views across the Ka'anapali Resort, and at the same time is very private, quiet, and peaceful. The huge 1600 provides a luxurious...

    Pool Hot Tub
    FREE CANCELLATION

    $274 to $686/night

  6. CONDOMINIUM
    Kaleialoha #113

    Kaleialoha #113

    LAHAINA, HI

    You will not be disappointed in this completely remodeled, ground floor unit. All the amenities of an upscale home including Granite counters, Travertine tile throughout and over sized walk in, glass block shower. King bed, In suite washer/ dryer...

    Pool
    FREE CANCELLATION

    $207 to $413/night

  7. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, 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

  8. CONDOMINIUM
    HOL #216

    HOL #216

    Lahaina, HI

    Relax in luxury at your newly remodeled direct oceanfront condo. Watch gorgeous sunsets from your large private lanai! See whales jumping in season! Condo has King size four poster bed. Ceiling fans in every room! Very nice sectional sofa! Condo...

    Pool
    FREE CANCELLATION

    $159 to $348/night

  9. CONDOMINIUM
    Kona Plaza#402

    Kona Plaza#402

    Kailua Kona, HI

    ***NEW PROPERTY IN VACATION RENTAL INVENTORY AS OF JUNE 2018!***Knutson & Associates Property Management is proud to be newly representing Kona Plaza#402. Welcome to the listing page of Kona Plaza#402!!! It's amazing location puts you right in...

    Pool
    FREE CANCELLATION

    $319 to $467/night

  10. CONDOMINIUM
    Kaleialoha #114

    Kaleialoha #114

    Lahaina, HI

    Completely Upgraded ground floor unit. Beautiful granite countertops in kitchen, ceramic stove top and new travertine tile throughout. Cal King bed, built in vanity, 2nd flat screen TV, in suite washer/dryer and A/C. Free internet, basic cable,...

    Pool
    FREE CANCELLATION

    $207 to $413/night

  11. CONDOMINIUM
    Hale Kona Kai Ko Olina Beach Villa (O1105)

    Hale Kona Kai Ko Olina Beach Villa (O1105)

    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

    $508 to $1,668/night

  12. CONDOMINIUM
    Hoyochi Nikko #201

    Hoyochi Nikko #201

    Lahaina, HI

    One bedroom with high vaulted ceilings (additional sleeping capacity on sofa bed in living room). Brand new memory foam mattress. This unit has air conditioning in the bedroom along with a comfortable queen size bed. This condo is fully equipped...

    Pool
    FREE CANCELLATION

    $218 to $319/night

  13. VILLA
    Waikoloa Beach Villas C3

    Waikoloa Beach Villas C3

    Waikoloa, HI

    This Villa is in an excellent location right at one of the two lava rock pools that Waikoloa Beach Villas has to offer. The property is located on the ground floor which comes with many benefits. No stairs to climb, which makes bringing groceries...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $431/night

  14. CONDOMINIUM
    Hale Lokahi KoOlina Beach Villa (O701)

    Hale Lokahi KoOlina Beach Villa (O701)

    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

    $397 to $1,204/night

  15. CONDOMINIUM
    Hale Hauoli Ko Olina Beach Villa (O404)

    Hale Hauoli Ko Olina Beach Villa (O404)

    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 is not reserved and can be...

    Pool Hot Tub

    $397 to $1,204/night

  16. CONDOMINIUM
    Aina Nalu C204

    Aina Nalu C204

    Lahaina, HI

    In the heart of historic Lahaina Town, Aina Nalu sits on a 9 acre OASIS of lush and tropical gardens with two swimming pools, spa, private Balinese bungalows at poolside, large pavilion and gas-fired BBQs. Unit 204 in building C is a beautiful two...

    Pool Hot Tub
    FREE CANCELLATION

    $230 to $410/night

  17. CONDOMINIUM
    Kaanapali Royal J202

    Kaanapali Royal J202

    Lahaina, HI

    A luxury condo in the heart of the Kaanapali Beach Resort. This beautiful two bedroom two bathroom condominium, surrounded by lush, tropical landscaping makes Kaanapali Royal a beautiful retreat in paradise. It is located in a gated community for...

    Pool Hot Tub
    FREE CANCELLATION

    $315 to $1,066/night

  18. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Wonderful ocean views from this spacious penthouse level studio. The owners have completed a beautiful remodel featuring tile floors and a new sofa-sleeper. The full kitchen was recently re-done with new appliances, granite counter tops, new...

    Pool Hot Tub
    FREE CANCELLATION

    $185 to $614/night

  19. CONDOMINIUM
    Hololani A303

    Hololani A303

    Lahaina, HI

    Stunning and Spectacular views from this West Maui oeachfront 2 bedroom 2 full bath condo. Just a short drive away from the famous Kaanapali Beach. Watch breaching whales just beyond the reef that protects the waters directly in front of the...

    Pool
    FREE CANCELLATION

    $199 to $499/night

  20. CONDOMINIUM
    Napili Point A8

    Napili Point A8

    Lahaina, HI

    Brand new tile throughout the entire condo! The bedroom has a comfortable King bed and TV to help you relax at the end of your day. The bathroom has a nice large vanity area separate from the toilet and walk-in shower area. The living room has a...

    Pool
    FREE CANCELLATION

    $228 to $469/night

  21. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    TROPICIAL LUXURY, ELEGANCE AND CHARM best describe this splendid 2 bedroom / 2 bath at Aina Nalu condominium. Abundant comforts await your arrival at this award winning and highly sought after Lahaina resort. You will be greeted to this 9 acre...

    Pool Hot Tub
    FREE CANCELLATION

    $189 to $645/night

  22. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Your dream Maui vacation awaits! Kamaole Sands 8-203 is on the second floor of building 8 in one of the most sought-after complexes in South Maui. This unit has been newly updated and has a brand new sofa sleeper in the living area and King mattress...

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $374/night

  23. CONDOMINIUM
    Maui Kai 605

    Maui Kai 605

    Lahaina, HI

    New listing from happy new owners! Remodel Scheduled For Spring 2020!! April 23rd - June 30th."E komo mai" (welcome) to spectacular Maui Kai 605! We have named this little slice of paradise "Ka Moe" (the dream) as this has been our dream come...

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $299/night

  24. CONDOMINIUM
    Kamahana 24

    Kamahana 24

    Princeville, HI

    This two bedroom, two full bath, upper floor end unit at the edge of the Kamahana complex features ocean, mountain, and golf course views from each room. As you end your day snuggled in the master bedroom's king bed, you'll fall asleep to the sound...

    Pool
    FREE CANCELLATION

    $183 to $214/night

  25. CONDOMINIUM
    Sealodge F9

    Sealodge F9

    Princeville, HI

    Private, top floor apartment with OCEAN FRONT views! Sealodge F9 is the only top floor condo in the building! Perfect for your honeymoon or other romantic getaway, it offers privacy, panoramic and unobstructed oceanfront views, and welcoming...

    Pool
    FREE CANCELLATION

    $214 to $238/night

  26. CONDOMINIUM
    Honua Kai- Konea 924- One Bedroom Ocean View! Renovated!

    Honua Kai- Konea 924- One Bedroom Ocean View! Renovated!...

    Kaanapali, HI

    NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the Konea building at Honua Kai. This condo overlooks the construction site. There may be noise and dust on work days during construction hours from 8am to 5pm.NOW FEATURING...

    Pool Hot Tub

    $305 to $1,003/night

  27. HOUSE
    Oceanfront 3BR, Breathtaking Views

    Oceanfront 3BR, Breathtaking Views

    Captain Cook, HI

    Located in Kealakekua Bay, a protected marine sanctuary and an ideal spot for snorkeling, diving, and kayaking, this 3BR/2BA oceanfront property is lovingly named Kaikanani (the beautiful sea) and sits right on the water’s edge. Look no further,...

    FREE CANCELLATION

    $248 to $561/night

  28. CONDOMINIUM
    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    Lahaina, HI

    PROPERTY OVERVIEWOverlooking both Lanai and Molokai, this 3BR/2.5BA condo offers the ultimate tropical getaway. Enjoy al fresco meals paired with ocean views on the private lanai or recline on lounge chairs with a refreshing beverage. Ensuring the...

    Pool
    FREE CANCELLATION

    $149 to $653/night

  29. CONDOMINIUM
    Aina Nalu A 201

    Aina Nalu A 201

    Lahaina, HI

    AINA NALU A-201 Welcomes you with Aloha...This unique condo in the heart of Old Lahaina Town is a perfect vacation spot!A-201 has been remodeled with a decor that speaks "ALOHA"Included in our fabulous price are many owner-supplied extras such...

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $371/night

  30. CONDOMINIUM
    Oceanfront Nohonani- Unforgettable Views

    Oceanfront Nohonani- Unforgettable Views

    Lahaina, HI

    This recently updated 2BR/2BA oceanfront condo at Nohonani offers incredible views of both Lanai and Molokai from its fourth-floor perch. Sip drinks on the private lanai while taking in the sunset over the Pacific.Enjoy resort-style amenities,...

    Pool
    FREE CANCELLATION

    $133 to $619/night