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
    The Montage Kapalua Bay Heliconia 2302

    The Montage Kapalua Bay Heliconia 2302

    Kapalua, HI

    Beautiful 3 bedroom/3.5 bath plus Den Residence. Heliconia Residence at Residences at Montage This beautiful 3 bedroom/3.5 bath plus Den home is situated in Building #2 at the Residences at Montage in beautiful Kapalua. Enjoy the ocean views from...

    Pool

    $1,049 to $5,972/night

  2. HOUSE
    Hale Grace Aloha

    Hale Grace Aloha

    Kailua Kona, HI

    Searching for vacation rentals with a private pool? Look no further because this is one of the best vacation rentals with a private pool on the Big Island. Nestled in an enclosed tropical garden across the way from the Ali’i outdoor marketplace...

    Pool

    $876 to $1,284/night

  3. 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 $3,474/night

  4. CONDOMINIUM
    760 South Kihei Condo Unit 414

    760 South Kihei Condo Unit 414

    Kihei, HI

    Feel Pacific breezes as you unwind on the lanai of your fourth-floor 3BR/2BA condo. This unit commands the most sought-after location in the building (front and center), closest to the ocean and furthest from the road. Take in stunning wide-open...

    Pool
    FREE CANCELLATION

    $607 to $794/night

  5. 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

    $565 to $945/night

  6. CONDOMINIUM
    Honua Kai Hokulani 709

    Honua Kai Hokulani 709

    Kaanapali, HI

    Never before offered for rental, Honua kai Hokulani 709 is clearly the best 2 bedroom condo available in the Hokulani Building. Top of the highly desirable "09" stack, it just doesn't get any better than this. The best Ocean views from INSIDE the...

    Pool Hot Tub

    $526 to $2,098/night

  7. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    One of the nicest penthouse units at Papakea Resort. From your lanai and the master bedroom, watch the whales play and the honu (turtles) swim. The KING bed in master bedroom allows you to sleep to the sounds of the ocean just 25 feet away. The...

    Pool Hot Tub

    $491 to $707/night

  8. 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

  9. HOUSE
    1332 Mokolea Dr Home

    1332 Mokolea Dr Home

    Kailua, HI

    Located in the upscale neighborhood of Lanikai, this 3BR/2BA ocean tree house is strolling distance to Lanikai Beach — regarded as one of the world's most beautiful top beaches, with its flour-soft white sands, cooling ocean breezes, and pristine...

    FREE CANCELLATION

    $484 to $803/night

  10. CONDOMINIUM
    Honua Kai Hokulani 841

    Honua Kai Hokulani 841

    Kaanapali, HI

    This large two bedroom/two bath condo in the hokulani interior courtyard is the perfect vacation spot. With 1320 sq ft of interior living space and an over sized 340 sq ft wraparound lanai, HOKULANI 841 is one of the largest two bedroom condos at...

    Pool Hot Tub

    $476 to $1,978/night

  11. CONDOMINIUM
    Honua Kai Hokulani 409

    Honua Kai Hokulani 409

    Kaanapali, HI

    This Beautiful Condo is in the Hokulani Enclave here at the beautiful Honua Kai Resort & Spa. This unique 2 bedroom/2 bath condo is an interior unit with a large lanai that wraps around the front of the condo overlooking the PACIFIC OCEAN, LANA'I,...

    Pool Hot Tub

    $466 to $1,776/night

  12. CONDOMINIUM
    Honua Kai Konea 642

    Honua Kai Konea 642

    Kaanapali, HI

    JUST RENOVATED AND GORGEOUS! All new hard surface flooring throughout and new living room furnishings! Lounge on the new sofa chaise and watch the waves crash while you enjoy a glass of your favorite wine or a great Hawaiian Kai Tai! Dine at the...

    Pool Hot Tub

    $436 to $1,491/night

  13. CONDOMINIUM
    Honua Kai Konea 643

    Honua Kai Konea 643

    Kaanapali, HI

    This great sixth floor 1315 square foot condo is in the interior courtyard of the Konea building with wonderful ocean views from the spacious lanai. Enjoy your morning coffee while watching the whales play in winter and the tours boats passing by...

    Pool Hot Tub

    $436 to $1,607/night

  14. HOUSE
    6307 Kaiwiki Pl Home

    6307 Kaiwiki Pl Home

    Honolulu, HI

    Property Overview Located on a quiet cul-de-sac just minutes from the ocean, this 3BR/2BA home is perfect for a serene tropical escape. Relax on the lanai or in the private yard and enjoy meals al fresco under the tall palms. Enjoy a prime location;...

    FREE CANCELLATION

    $402 to $778/night

  15. HOUSE
    Pua Nui

    Pua Nui

    Princeville, HI

    PUA NUI - House of Abundant Flowers TA-149-751-5008-01 This extremely lovely and comfortable Princeville home has four bedrooms - including two master suites, and three full baths. The home sleeps 8 guests. The huge lanai overlooks the lush...

    FREE CANCELLATION

    $386 to $505/night

  16. CONDOMINIUM
    Maui Eldorado I204/205

    Maui Eldorado I204/205

    Lahaina, HI

    Picture yourself sitting on one of your two private lanai's while overlooking the 4th green of the Royal Golf Course at Kaanapali and experiencing views of the blue Pacific ocean, sunsets, winter whale watching and the island of Molokai. Our...

    Pool
    FREE CANCELLATION

    $383 to $551/night

  17. CONDOMINIUM
    Kanai A Nalu 417

    Kanai A Nalu 417

    Maalaea, HI

    Kanai A Nalu #417 is registered as a Transient Accommodation. Owner Registration I.D.TA-107-061-2480-01 Kanai A Nalu has been rated The Best Vacation Property in Ma'alaea. Spectacular ocean vistas are guaranteed in this specially designed...

    Pool
    FREE CANCELLATION

    $340 to $447/night

  18. VILLA
    Kapalua Bay Villa 29G5 Ocean Front

    Kapalua Bay Villa 29G5 Ocean Front

    Kapalua, HI

    Beauty surrounds you in this lovely 1 bedroom 2 bath split level villa. One of few with an ocean view from the master suite! Just steps from the pools and beaches, a short walk to great restaurants, golf and tennis, this lovely two story ocean front...

    Pool

    $325 to $536/night

  19. CONDOMINIUM
    Kauhale Makai Condo #212

    Kauhale Makai Condo #212

    Kihei, HI

    New to the Market! Two bedroom ocean view condo at the Kauhale Makai, Village by the Sea. This condo has two bedrooms and two bathrooms and will accommodate up to six people. The master bedroom has a King bed, the second bedroom has two twin beds...

    Pool Hot Tub
    FREE CANCELLATION

    $321 to $411/night

  20. VILLA
    Bay Villa 15G5 Ocean View

    Bay Villa 15G5 Ocean View

    Kapalua, HI

    These amenities are included for your comfort and convenience: **no need to scramble for a grocery store when you arrive. Send us your list. We'll make sure your villa is well stocked with your favorites! You pay only for the cost of groceries....

    Pool

    $319 to $576/night

  21. CONDOMINIUM
    Kaanapali Shores 259

    Kaanapali Shores 259

    Kaanapali, HI

    Best Ocean View Condo At Kaanapali Shores and JUST RENOVATED! This amazing condo has just been updated with new Luxury Vinyl Plank Flooring throughout and new modern furnishings including a great new Sofa/sleeper with brand new 6" mattress! (New...

    Pool Hot Tub

    $317 to $1,223/night

  22. CONDOMINIUM
    Honua Kai Konea 1026

    Honua Kai Konea 1026

    Lahaina, 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. This beautiful...

    Pool Hot Tub

    $317 to $1,353/night

  23. CONDOMINIUM
    Honua Kai Hokulani 712

    Honua Kai Hokulani 712

    Kaanapali, HI

    Located on the South side of the Hokulani tower, this top floor (7th floor) unit has great Ocean Views with the island of Lana'i in the background! This beautiful 2 bedroom floor plan is being rented as a 1 bedroom, 1 bath, King bed in bedroom with...

    Pool Hot Tub

    $316 to $1,033/night

  24. CONDOMINIUM
    Honua Kai Konea 312

    Honua Kai Konea 312

    Kaanapali, HI

    UPGRADED 2 PLUS ONE!!! Two Bedroom One Bath! West Maui Mountain & Waterfall Views! 915 sq ft! Just renovated with new DESIGNER FURNISHINGS, new flooring and a brand new Queen Bed in the Private Den! New Flat screen 4K TV's with built in Netflix,...

    Pool Hot Tub

    $316 to $1,211/night

  25. CONDOMINIUM
    Kaanapali Shores 403

    Kaanapali Shores 403

    Lahaina, HI

    Relax on our 4th floor lanai, overlooking the ocean, well-kept grounds and pool at Kaanapali Shores! Kaanapali Shores resort is located on the beach in North Kaanapali. Unit 403 lanai has views of the ocean,spectacular sunsets, and whales in...

    Pool
    FREE CANCELLATION

    $311 to $938/night

  26. CONDOMINIUM
    Honua Kai Konea 606

    Honua Kai Konea 606

    Kaanapali, HI

    NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the Konea building at Honua kai. There may be noise and dust on work days during construction hours from 8am to 5pm. Konea 606 is a large 945 square foot (plus 180 sq ft Lanai)...

    Pool Hot Tub

    $299 to $1,211/night

  27. CONDOMINIUM
    Maui Eldorado B206

    Maui Eldorado B206

    Kaanapali, HI

    GREAT UPGRADED 2 BEDROOM!!! Beautiful 1,440 sq ft upgraded 2 bedroom/2bath condo! Beautiful 2bed/2bath, open living space design with over 1400 sq ft of luxury! This second floor, end location is tastefully remodeled with finishes that include...

    Pool

    $287 to $1,074/night

  28. CONDOMINIUM
    Maui Eldorado D200

    Maui Eldorado D200

    Kaanapali, HI

    LIGHT & BRIGHT CORNER 2 BEDROOM!!! Beautiful 1,440 sq ft 2 bedroom/2bath condo with Peakaboo Ocean View! Never before offered for rental! What a find! The oversized covered lanai of this second floor, end location is the perfect spot to relax...

    Pool

    $287 to $1,074/night

  29. CONDOMINIUM
    Honua Kai Hokulani 108

    Honua Kai Hokulani 108

    Kaanapali, HI

    Beautiful Ground Floor One Bedroom at Honua kai! This great Ground Floor unit provides easy access to all Honua kai has to offer. With its large syn-grass lawn there is ample room for the kids to play or to just relax and enjoy the day. The beach...

    Pool Hot Tub

    $286 to $1,033/night

  30. CONDOMINIUM
    Honua Kai Konea 144

    Honua Kai Konea 144

    Kaanapali, HI

    Beautiful Ground Floor One Bedroom at Honua kai! This great North Facing Ground Floor unit provides easy access to all Honua kai has to offer. With its private large lawn there is ample room for the kids to play or to just relax and enjoy the day....

    Pool Hot Tub

    $286 to $1,033/night