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
    Fairway Villas Waikoloa N21

    Fairway Villas Waikoloa N21

    Waikoloa, HI

    Stay in our lovely 2 Bedroom 2 Bath villa overlooking the lake located in the Waikoloa Resort area. Just painted and furnished with new appliances and furniture. Master bedroom has a king bed, on suite full bathroom, master closet and a flat screen...

    Pool Hot Tub
    FREE CANCELLATION

    $184 to $407/night

  2. CONDOMINIUM
    Lauloa 105

    Lauloa 105

    Wailuku, HI

    Start your Maui vacation off right! Watch the sun rise of Haleakala with a cup of coffee, or watch the sunset from the comfort of your lanai. See the Honu (Sea Turtles) play just outside your door or watch the surfers on the legendary surf break...

    Pool
    FREE CANCELLATION

    $244 to $438/night

  3. CONDOMINIUM
    Aina Nalu K102

    Aina Nalu K102

    Lahaina, HI

    This 2 bedroom condo is extremely well furnished, with everything you need to make your stay wonderful, giving you maximum comfort. The unit is well lit, with an AC unit in each room. Stainless steel appliances, wireless internet, and flat screen...

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $723/night

  4. CONDOMINIUM
    Kaleialoha 211

    Kaleialoha 211

    Lahaina, HI

    This beautiful 1 bedroom, 1 bathroom oceanfront condominium provides everything you need for your vacation in paradise. With spectacular panoramic views over Maui’s neighbor islands, Lanai and Molokai, you can’t beat watching the whales and...

    Pool
    FREE CANCELLATION

    $174 to $319/night

  5. CONDOMINIUM
    Paki Maui 414

    Paki Maui 414

    Lahaina, HI

    Come enjoy the Paki Maui Oceanfront Resort! This 1 bedroom, 1 bath, lush garden view condo is the perfect place for couples, small families and adventurers looking to experience and explore the island for all the wondrous places and memories it...

    Pool
    FREE CANCELLATION

    $154 to $503/night

  6. CONDOMINIUM
    Mauna Kai 5A

    Mauna Kai 5A

    Princeville, HI

    Mauna Kai is a charming townhome complex in central Princeville. The walk to north shore Anini Beach - a beautiful, uncrowded, white-sand beach - is a brief 12-minutes along a shady tree-lined path. Shopping and dining in Princeville are also easy...

    Pool
    FREE CANCELLATION

    $214 to $238/night

  7. 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

  8. CONDOMINIUM
    Honua Kai Konea 1019

    Honua Kai Konea 1019

    Kaanapali, HI

    Unbelievable KONEA 10th FLOOR CORNER PENTHOUSE -PANORAMIC VIEWS above the resort not looking into the courtyard. The 180 degree view of the blue pacific ocean, the islands of lanai and molokai, Black Rock and Maui Mountains! One of only four homes...

    Pool Hot Tub

    $853 to $3,313/night

  9. CONDOMINIUM
    Ali'i Kai 4303

    Ali'i Kai 4303

    Princeville, HI

    A Million Dollar View! Take in the phenomenal Hawaiian wildlife from this 20 ft. lanai - whales, spinner dolphins and more. View the ~180 degree coastline from the beacon of the Kilauea lighthouse to sunsets over Bali Hai on the West. With the...

    Pool
    FREE CANCELLATION

    $122 to $527/night

  10. CONDOMINIUM
    Villas of Kamalii 44

    Villas of Kamalii 44

    Princeville, HI

    Enjoy comfort and luxury in this three bedroom/three bathroom townhouse with spectacular mountain and waterfall views, heated salt water pool, and jacuzzi. Located in a gated community adjacent to the Makai golf course, Villas of Kamalii 44 boasts a...

    Pool Hot Tub
    FREE CANCELLATION

    $240 to $624/night

  11. CONDOMINIUM
    Kaleialoha 402

    Kaleialoha 402

    Lahaina, HI

    Aloha! Come stay with us at the beautiful Kaleialoha Oceanfront Resort!! This is a fully furnished Studio that sleeps 4 with everything that you will need to enjoy your paradise vacation. There is a Queen sized bed and a Queen sofa sleeper! There is...

    Pool
    FREE CANCELLATION

    $148 to $549/night

  12. CONDOMINIUM
    Eldorado K203

    Eldorado K203

    Lahaina, HI

    This 2nd floor, spacious, air-conditioned condo is a single bedroom and a studio all in one, to basically make an incredible 2 bedroom 2 Bathroom home! The two rooms are completely separated with their own private lockable doors, and each has its...

    Pool Hot Tub
    FREE CANCELLATION

    $250 to $500/night

  13. CONDOMINIUM
    Paki Maui Unit #109 Condo

    Paki Maui Unit #109 Condo

    Honokowai, 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

  14. CONDOMINIUM
    Papakea Unit #J107 Condo

    Papakea Unit #J107 Condo

    Kaanapali, HI

    Remodeled ground floor 1 bedroom in North Ka’anapali. End unit with plenty of natural light and view of koi pond and lush gardens. Open and airy with white plantation kitchen cabinets and room doors and tiled living areas and lanai. The lanai...

    Pool
    FREE CANCELLATION

    $203 to $414/night

  15. CONDOMINIUM
    Maui Kamaole #A-201

    Maui Kamaole #A-201

    Kihei, HI

    Kamaole Beach #3 is just across from the upscale Maui Kamaole. This property features lush tropical landscaping and beautiful ocean views, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the...

    Pool
    FREE CANCELLATION

    $304 to $459/night

  16. BUNGALOW
    He'eia Bay Beach Bungalow (Big Island)

    He'eia Bay Beach Bungalow (Big Island)

    Kailua Kona, HI

    Located in a very desirable neighborhood, the Keauhou subdivision, this beautifully remodeled home sits right on the Kona Country Club Golf Course and offers exceptional golf course views! This home is surrounded by beauty and is directly across...

    $304 to $702/night

  17. 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

  18. 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

  19. HOUSE
    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    Kailua Kona, HI

    ***Please note there is a 7 night minimum during the holidays. Christmas reservations must check out by 10AM on Dec. 27 and New Year's reservations can check in on Dec. 27 or after for a week. There is a 14 night minimum to book both Christmas and...

    Pool

    $482 to $720/night

  20. CONDOMINIUM
    Ali'i Kai 2101

    Ali'i Kai 2101

    Princeville, HI

    Retreat to this quiet newly decorated home overlooking the mountains and waterfalls with distant ocean views. This ground floor, corner unit offers comfortable furnishings for rest and relaxation. Corner location on the green belt makes this a great...

    Pool
    FREE CANCELLATION

    $162 to $527/night

  21. CONDOMINIUM
    Sealodge J3

    Sealodge J3

    Princeville, HI

    Absolutely spectacular unobstructed reef and white-water ocean views from the living room and bedroom of this cozy 1 BR corner unit in the end building of Sealodge II. This ground floor unit (Sealodge J3) gives you immediate outdoor access to the...

    Pool
    FREE CANCELLATION

    $122 to $524/night

  22. CONDOMINIUM
    Pali Ke Kua 119

    Pali Ke Kua 119

    Princeville, HI

    AIR CONDITIONED BEDROOM IN LUXURY HAVEN - a very private location. Behind you, a lush green hill; to the left, another tropical hill separates Pali Ke Kua 119 from the world. Straight ahead, in full view...Bali Hai, sunsets and the indefinite...

    Pool Hot Tub
    FREE CANCELLATION

    $156 to $631/night

  23. ESTATE
    Kailua Shores Estate

    Kailua Shores Estate

    Kailua, HI

    One of the largest, most private and secluded Estates on the island of Oahu. A spectacular beachfront location-at Kailua Shores Estate with the comfort of a resort, consisting of separate houses, newly remodeled, set on extensive grounds featuring a...

    Pool

    $7,860 to $12,620/night

  24. CONDOMINIUM
    Kona Makai 1-301

    Kona Makai 1-301

    Kailua Kona, HI

    Kona Makai #1-301 is arguably the best condo in the entire complex. Being the top floor corner in building 1, the location is undeniably too perfect. Private & upgraded, this is direct oceanfront condo living at its finest. You can't get a better...

    Pool Hot Tub
    FREE CANCELLATION
  25. TOWNHOUSE
    Pili Mai 11I

    Pili Mai 11I

    Koloa, HI

    Enjoy modern Hawaii living at Pili Mai 11I Pack your golf clubs and get ready to enjoy modern Hawaii living in this exclusive Poipu community. Located on the 9th hole of the beautiful Kiahuna Golf Course, this exceptionally beautiful,...

    Pool Hot Tub

    $470 to $1,150/night

  26. CONDOMINIUM
    Kihei Bay Surf #109

    Kihei Bay Surf #109

    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

    $115 to $186/night

  27. CONDOMINIUM
    Poipu Shores B202

    Poipu Shores B202

    Koloa, HI

    This second floor 2br/1ba condo has two king beds, with air-conditioning in each bedroom and in the living room. Poipu Shores B202 has a full kitchen, updated with elegant granite counters, and one bathroom, recently remodeled. Enjoy a private...

    Pool
    FREE CANCELLATION

    $402 to $1,141/night

  28. CONDOMINIUM
    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    Kihei, HI

    Maalaea Surf, Unit A5 is a townhouse unit on the second floor which offers our guest total privacy and is located beach front on the property. This loft suite with 2 baths is very well furnished. Enjoy ocean front outdoor living on your spacious...

    FREE CANCELLATION

    $304 to $467/night

  29. CONDOMINIUM
    1 Bedroom Corner Oceanfront 308

    1 Bedroom Corner Oceanfront 308

    Kaanapali, HI

    One Bedroom Corner - King Bed, NO sofa bed, Flat screen TV - hardwood floors; Livingroom is tiled in white. This condo will accommodate a maximum of two people. The unit has a fabulous panoramic view of the beach below and the neighboring islands....

    Pool Hot Tub
    FREE CANCELLATION

    $351 to $423/night

  30. HOUSE
    My Hilo Home

    My Hilo Home

    Hilo, HI

    Prices Discounted through June 15 Enter the home onto the grand lanai (porch) which is fully screened in and offers a view of the manicured acre with Hilo Bay views in the distance. Through the front doors you'll be greeted by our huge living room....

    $321 to $626/night