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.

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters
  1. APARTMENT
    Diamond Head Beach Hotel 303

    Diamond Head Beach Hotel 303

    Honolulu, HI

     Legal vacation rental -  2947 Kalakaua Ave, #303  Whether for business or pleasure the delightful attention to detail Wins! Located at the foot of the iconic Diamond Head crater, this home away from home has everything you need for either...

    FREE CANCELLATION

    $153 to $219/night

  2. CONDOMINIUM
    Palekaiko (Paradise)

    Palekaiko (Paradise)

    Waikoloa Village, HI

    This quiet beautifully remodeled 1400sf 2 bedroom condo is located at a comfortable 900 feet elevation right on the 9th Fairway of the Robert Trent Jones Jr. designed Golf Course in Waikoloa Village. The Waikoloa Villas complex is surrounded by lush...

    Pool Hot Tub

    $158 to $210/night

  3. CONDOMINIUM
    Waikoloa Beach Villas M2

    Waikoloa Beach Villas M2

    Waikoloa, HI

    Discover the spirit of Aloha! Tucked away next to one of the Aloha states largest and most luxurious resorts, this 2 bedroom 2 bathroom villa is a destination in itself. Located on the golf course, and only a few minutes walk from the beach, there...

    Pool Hot Tub
    FREE CANCELLATION

    $172 to $431/night

  4. CONDOMINIUM
    Kihei Bay Surf #208

    Kihei Bay Surf #208

    Kihei, HI

    The Kihei Bay Surf is located in North Kihei across the street from the Whale Sanctuary and Kalepolepo Beach and an ancient Hawaiian fishpond. Each studio has a fully equipped kitchen and cable TV. In addition, there is a large pool, hot tub, tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $103 to $173/night

  5. CONDOMINIUM
    Kihei Bay Vista #C-101

    Kihei Bay Vista #C-101

    Kihei, HI

    Kihei Bay Vista is just across the street from the Whale Sanctuary and a very long stretch of beach. Windsurf, Whale watch, walk the beach and enjoy unbelievable sunsets. The complex features a lovely pool, hot tub and gas grills for your use. There...

    Pool Hot Tub
    FREE CANCELLATION

    $126 to $231/night

  6. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Our well-appointed home has everything you could possible need. Fresh, home grown mango, guava and finger lime for our guests to feast on . Enjoy the relaxing sound of the cascading rush of your private pool's waterfall. The lush golf green views...

    Pool Hot Tub

    $1,917 to $5,992/night

  7. CONDOMINIUM
    164

    164

    Kihei, HI

    Luxuriously updated one bedroom unit in excellent location, close to lower pools, bbq and office; with ocean view from the lanai. Furnished in Hawaiian style with beautiful wood cabinets in kitchen and bathroom, rattan in living room and bedroom,...

    Pool
    FREE CANCELLATION

    $188 to $270/night

  8. CONDOMINIUM
    217

    217

    Kihei, HI

    Great Garden and Ocean view. New living room furniture, two lazy boy chairs along with queen hide-a-bed. King bed bought in 2013 in bedroom with rattan furniture. Nice, spacious, updated kitchen and appliances. 42 inch flat screen TV, safe in unit...

    Pool
    FREE CANCELLATION

    $188 to $270/night

  9. CONDOMINIUM
    171

    171

    Kihei, HI

    This Maui vacation condo has a Contemporary Hawaiian style.The owners of this condo prefer only 2 adults and no large group/wedding party rentals. Starting in the living room enjoy the comfortable stuffed sitting chairs. A 46 inch HD Tv in the...

    Pool
    FREE CANCELLATION

    $188 to $297/night

  10. CONDOMINIUM
    Kona Plaza#220

    Kona Plaza#220

    Kailua Kona, HI

    Welcome to the listing page of Kona Plaza#220! It's amazing location puts you right in immediate walking distance to restaurants, beaches, shopping & entertainment right in the heart of Kailua Village.This comfortable 1 bedroom, 1 bath that sleeps 4...

    Pool
    FREE CANCELLATION

    $205 to $467/night

  11. HOUSE
    Ono Hale

    Ono Hale

    Kailua Kona, HI

    We welcome you to stay at our private luxury home (Ono Hale) in the lush hills above historic Kailua Kona. Located just minutes from town and Kona’s beautiful sandy beaches.Cool and quiet. Ono Hale is situated on a very private lot on a quiet...

    Pool
    FREE CANCELLATION

    $523 to $525/night

  12. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #6-104

    Keauhou Kona Surf & Racquet Club #6-104

    Kailua Kona, HI

    **BRAND NEW PROPERTY IN OUR INVENTORY! AIR CONDITIONING INSTALLED AS OF SEPTEMBER 2018!**Unit#6-104 is a well-maintained 2BR/2BA ground floor unit in a 15-acre, gated oceanfront complex at the Keauhou Kona Surf & Racquet Club. It's also an end...

    Pool
    FREE CANCELLATION

    $256 to $292/night

  13. 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

  14. APARTMENT
    KV403A 2450 Prince Edward St Honolulu THTH-PTO-00-CHK

    KV403A 2450 Prince Edward St Honolulu THTH-PTO-00-CHK

    Honolulu, HI

    Enjoy this studio with plenty of sleeping room for your guests!! There is a Queen size bed and Futon Couch, air conditioner, Cable TV is available on large 32" flat screen TV, mounted on wall for easy viewing. The kitchenette includes all cooking...

    FREE CANCELLATION

    $113 to $161/night

  15. HOUSE
    Junior Suite Oceanfront #607

    Junior Suite Oceanfront #607

    Lahaina, HI

    This beautiful sixth floor oceanfront condo has a perfect view of Molokai. The tropical décor and king murphy bed help make your stay comfortable and relaxing. The fully equipped kitchen is great for a quick bite or a full meal. You will find...

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $341/night

  16. CONDOMINIUM
    Kamaole Sands #8-208

    Kamaole Sands #8-208

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Located across the street from Kamaole Beach III. A 2 minute walk from the beach park and a 2 minute drive to Shops at Wailea, golf courses and dining makes Kamaole Sands a great 'destination'...

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $289/night

  17. CONDOMINIUM
    Fairway Villas Waikoloa A21

    Fairway Villas Waikoloa A21

    Waikoloa, HI

    Enjoy our 2 bedroom / 2 bath home for you and your family quietly tucked away along the Big Island's sunny Kohala Coast, Fairway Villas Waikoloa offers the crisp style, gracious elegance, and modern sophistication. The master bedroom has a king bed...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $407/night

  18. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Book a memorable Maui vacation at this third-floor 1BR condo in central Kihei. With open-concept living and an additional sleeper sofa, there’s plenty of room for four people. Step out to your private lanai with retractable net enclosure and take...

    Pool
    FREE CANCELLATION

    $115 to $326/night

  19. CONDOMINIUM
    Ilikai 1110

    Ilikai 1110

    Waikiki, HI

    OCEAN VIEWS! STEPS TO WAIKIKI BEACH. 2 bedroom, 2 full bathrooms, two 120 sq. ft lanais, 1,000 interior sq. ft. Walking distance to parks, shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life.The Ilikai Suites are...

    Pool
    FREE CANCELLATION

    $349 to $576/night

  20. CONDOMINIUM
    Royal Mauian #410

    Royal Mauian #410

    Kihei, HI

    The Royal Mauian is one of the premier properties of Kihei Maui. This Maui beachfront rental is located right on the beach between Kamaole Beach Park I and II. Featuring an oceanfront pool perched right at the water's edge. The lush landscaped...

    Pool
    FREE CANCELLATION

    $335 to $522/night

  21. CONDOMINIUM
    Kaleialoha #115

    Kaleialoha #115

    Lahaina, HI

    Lovely corner unit with all one side louvered windows to let the outside in!Recently upgraded with gorgeous granite counter, all new appliances and tile through out! Unit has unique four poster bed, walk in tiled shower, AC in living area, in suite...

    Pool
    FREE CANCELLATION

    $207 to $413/night

  22. CONDOMINIUM
    HOL 119

    HOL 119

    Lahaina, HI

    Beautifully updated ground floor unit. Private and unique! Enter through your own private entrance and enjoy the distinctive qualities of this exceptional condo! Large lanai with direct ocean views! A/C in both bedrooms. All stainless steel...

    Pool
    FREE CANCELLATION

    $277 to $531/night

  23. CONDOMINIUM
    Hoyochi Nikko #109

    Hoyochi Nikko #109

    Lahaina, HI

    One bedroom condo located in beautiful west Maui. For those wishing additional solitude, this is an end unit with a new queen bed and bedroom air conditioning. All units are fully equipped with Cable TV, DVD, CD player, washer/dryer, and...

    Pool
    FREE CANCELLATION

    $201 to $319/night

  24. CONDOMINIUM
    Kaleialoha #214

    Kaleialoha #214

    Lahaina, HI

    Beautiful, newly remodeled 2nd floor. All new furnishings including King Bed. Brand new carpeting! Upgraded bath has tub/shower combo. Brand new queen size sofa sleeper. Ceramic stove top in open kitchen. 2nd floor on end offers privacy and...

    Pool
    FREE CANCELLATION

    $195 to $384/night

  25. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    An incredibly comfortable unit! This renovated one bedroom unit fronts directly on a beautiful white sand beach. You'll have just enough lawn area to stretch out and shake the sand off before stepping directly into your beautiful ocean side living...

    FREE CANCELLATION

    $195 to $308/night

  26. CONDOMINIUM
    Kihei Akahi Resort- Unit C405

    Kihei Akahi Resort- Unit C405

    Kihei, HI

    Nice ocean and garden views! 4th Floor comfortable beach home - Building C.Kihei Akahi Resort C405 - Ocean View One Bedroom One Bath 655 sq. ft. located on the 4th floor, in building C.Enjoy great views from your lanai (balcony) of the Pacific...

    Pool
    FREE CANCELLATION

    $135 to $353/night

  27. CONDOMINIUM
    Koa Lagoon #206

    Koa Lagoon #206

    Kihei, HI

    The Koa Lagoon is an ocean front condominium complex in North Kihei with spectacular panoramic views of the Pacific ocean and Mauna Kahalawai, also known as the West Maui Mountains. Situated just 15 minutes from Kahului Airport on Sugar Beach, Koa...

    Pool
    FREE CANCELLATION

    $208 to $348/night

  28. CONDOMINIUM
    Menehune Shores #425

    Menehune Shores #425

    Kihei, HI

    Menehune Shores #425 is an oceanfront ocean view unit with a gorgeous view of the ocean. It is a 2 bedroom 2 bath unit with a fully equipped kitchen, washer and dryer, and internet service. Long distance calling to the US Mainland and Canada is...

    Pool
    FREE CANCELLATION

    $208 to $347/night

  29. CONDOMINIUM
    Luana Kai #A-103

    Luana Kai #A-103

    Kihei, HI

    Luana Kai is a large oceanfront complex in Kihei. It is centrally located to shops, activities, and restaurants. It features a large oceanfront pool, hot tub, shuffleboard, and gas grills for your use. There is an expansive lawn between the...

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $418/night

  30. CONDOMINIUM
    Maui Sunset #A-117

    Maui Sunset #A-117

    Kihei, HI

    Maui Sunset is a fabulous oceanfront property in Kihei that has lush tropical landscaping, large pool which is heated during the winter months, hot tub, gas grills, workout room, and tennis courts out on the beach for your use. Guests return here...

    Pool Hot Tub
    FREE CANCELLATION

    $167 to $254/night