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
    Hale Waiulu #150470

    Hale Waiulu #150470

    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 of...

    Pool Hot Tub

    $2,022 to $6,318/night

  2. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    One of West Maui's most exclusive legally permitted rental properties, the Makena Aloha Estate offers exceptional ocean and mountain views, with gated exclusive privacy and seclusion. With 4,400 square feet of interior dwelling space, this...

    Pool

    $1,968 to $3,075/night

  3. HOUSE
    Papaua Estate

    Papaua Estate

    Lahaina, HI

    APPROVED MAUI SHORT TERM RENTAL HOUSE #STWM 2104/0003. You and your family and friends will love your stay here for a vacation filled with Aloha! If you are looking for location, luxury and Hawaiian life style, you have found it. Perhaps the most...

    Hot Tub
    FREE CANCELLATION

    $1,869 to $2,874/night

  4. VILLA
    Hualalai Resort Ocean Front Golf Villa 4202

    Hualalai Resort Ocean Front Golf Villa 4202

    Kailua Kona, HI

    Whale watch while listening to the breaking waves from the shoreline from the Master bedroom's private lanai with unobstructed ocean views! This beautifully appointed three bedroom villa has over 2,500 square feet of living area. Each of the three...

    FREE CANCELLATION

    $1,751 to $5,546/night

  5. HOUSE
    Rainbow Hale Estate

    Rainbow Hale Estate

    Lahaina, HI

    Maui's Premier Vacation Home! Rainbow Hale Estate Kaanapali! Family Retreat, Private Honeymoon Retreat! Surrounded by 5 acres of Maui tropical plantation, lies a BRAND NEW spectacular estate you've always dreamed of, with the lifestyle you've always...

    Pool

    $1,661 to $2,429/night

  6. VILLA
    Hualalai Resort Palm Villa 140B

    Hualalai Resort Palm Villa 140B

    Kailua-Kona, HI

    This Hualalai Palm Villa is a spectacular three bedroom, three bath, two-story Hualalai condo on popular Waiulu Street at the world renowned Hualalai Resort. The Resort is home to the Four Seasons Hualalai, regarded by many as the #1 Resort in...

    Pool
    FREE CANCELLATION

    $1,401 to $3,736/night

  7. TOWNHOUSE
    Hualalai Resort Haliipua Villa 104

    Hualalai Resort Haliipua Villa 104

    Kailua-Kona, HI

    Built in 2009, Haliipua Villas are the newest generation of multi-family villas at Hualalai offering an array of designer finishes throughout the home. Special features include luxurious mahogany finishes, island-inspired ceiling treatments,...

    FREE CANCELLATION

    $1,401 to $3,736/night

  8. VILLA
    Hualalai Resort Fairway Villa 116D

    Hualalai Resort Fairway Villa 116D

    Kailua-Kona, HI

    Located on popular Waiulu Street just three minutes by golf cart to the Four Seasons Resort Hualalai, this large three bedroom single-level villa offers views of the 15th hole of the Hualalai Golf Course and ocean beyond. The villa is professionally...

    Pool
    FREE CANCELLATION

    $1,284 to $3,736/night

  9. VILLA
    Kapalua Bay Villa 21B2

    Kapalua Bay Villa 21B2

    Kapalua, HI

    This gorgeous Beach Front Villa occupies the top two floors of building 21. It has two completely private master bedrooms with en-suite. Main floor master has a private lanai. Both master suites have spectacular ocean views. There are 3 bathrooms;...

    Pool

    $1,254 to $1,898/night

  10. HOUSE
    Pua Lani Home 69-1854

    Pua Lani Home 69-1854

    Waimea, HI

    A sophisticated touch of "old Hawaii" with easy ocean front living.  Large open spaces, Ocean views from two master suites, kitchen and living room with expansive covered lanai across the ocean side of the home.  Enter into two private landscaped...

    Pool

    $1,210 to $2,420/night

  11. VILLA
    Hualalai Palm Villa 140C

    Hualalai Palm Villa 140C

    Kailua-Kona, HI

    The spacious floor plan includes a downstairs master bedroom suite with king bed and luxury spa-like bath. Just off the master is a large living room with queen sized sofa pull out that opens to the downstairs lanai, leading to the lawn and golf...

    Pool
    FREE CANCELLATION

    $1,168 to $3,736/night

  12. VILLA
    Hualalai Resort- Waiulu 137D

    Hualalai Resort- Waiulu 137D

    Kailua-Kona, HI

    This spacious 3 bedroom, 3.5 bath single-level villa is centrally located on the Resort’s popular Waiulu Street overlooking beautiful Punawai Pond, the 5th Hole of the Member’s Ke`olu Golf Course and the ocean beyond. With 2642 square feet of...

    Pool
    FREE CANCELLATION

    $1,168 to $3,736/night

  13. VILLA
    Hualalai Resort Hillside 4102

    Hualalai Resort Hillside 4102

    Kailua-Kona, HI

    Location-Location-Location! This spectacular 2 bedroom, 2 bath luxury villa is a short distance to the Four Seasons Resort Hualalai - truly one of the worlds' great resorts. Enjoy the soothing sounds of gentle waves on the shoreline from this ground...

    Pool
    FREE CANCELLATION

    $1,109 to $3,736/night

  14. VILLA
    Hualalai Resort Ke Alaula Villa 210A

    Hualalai Resort Ke Alaula Villa 210A

    Kailua-Kona, HI

    Spectacular three bedroom three bath villa centrally located within the Hualalai Resort. Two story townhome style in the exclusive Ke Alaula neighborhood, just a 3-4 minute cart ride to the Four Seasons Hotel. Fully receding pocket glass, screen and...

    FREE CANCELLATION

    $1,109 to $3,736/night

  15. TOWNHOUSE
    Hale Lani Ko Olina Kai Villa (1077E)

    Hale Lani Ko Olina Kai Villa (1077E)

    Kapolei, HI

    At Hale Lani Villa, you can walk to the beach in 10 minutes or drive there in 2! The 3 BR, 2 BA villa is conveniently located just 20 miles from Honolulu International Airport on the beautiful southwestern shores of Oahu. The resort offers four...

    Pool
  16. VILLA
    Hualalai Resort Fairway Villa 104D

    Hualalai Resort Fairway Villa 104D

    Kailua-Kona, HI

    Upper level 2-bedroom, 2-bath villa overlooking the 15th tee of the Hualalai Golf Course with stunning Mauna Kea, Island of Maui and horizon views of the ocean. Designed by Honolulu-based Architect Warren Sunnland, the Fairway Villas at Hualalai are...

    Pool
    FREE CANCELLATION

    $934 to $2,335/night

  17. VILLA
    Hualalai Resort Fairway Villa 110C

    Hualalai Resort Fairway Villa 110C

    Kailua Kona, HI

    This garden level 2 bedroom, 2 bath Fairway Villa overlooks the 15th Fairway of the Hualalai Golf Course with views of the ocean beyond. Located within the master-planned resort community of Hualalai, guests have the option of amenity use privileges...

    FREE CANCELLATION

    $934 to $2,335/night

  18. HOUSE
    Kainoa

    Kainoa

    Hanalei, HI

    KAINOA:TVNCU-1227: TA#148-488-1920-01 Walk to Hanalei Bay or to Hanalei shops and restaurants This beautifully appointed 4 bedroom, (two master suites) and 3 bath home with Hawaiian and Asian flair. Hardwood floors extend out to the deck in a...

    Hot Tub

    $881 to $1,110/night

  19. HOUSE
    Hale A Kai

    Hale A Kai

    Princeville, HI

    This beautiful custom home is located in the Queen Emma Bluff's gated community in Princeville. The home is approximately 4000 sq feet. Upstairs is a large great room with beautiful hardwood floors. There’s a well equipped gourmet kitchen with a...

    $842 to $1,149/night

  20. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Oceanfront estate with breathtaking panoramic unobstructed views. 4 BR, 4 elegant baths. All bedrooms have oceanfront balconies. Walls of glass open to lanai & main living area making this an ideal Hawaiian indoor/outdoor living experience. Elegant...

    Pool Hot Tub

    $766 to $846/night

  21. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This beautiful custom home, built in 2007, boasts 5 buildings totaling interior 3,829 sq. feet; including main house, and a private master suite situated at each of 4 corners. Main house has a private study converted to bedroom with a sink, a half...

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1,540/night

  22. CONDOMINIUM
    Wailea Elua #2204

    Wailea Elua #2204

    Wailea, Maui, HI

    You will immediately sense that the fabulous Maui vacation you have been looking forward to has begun when you step into this completely remodeled 2 bedroom, 2 bath condo located on one of the best locations in the Wailea Elua Village. From our...

    Pool

    $724 to $1,065/night

  23. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Welcome to Hale Lani. This gorgeous house is a Brand New Vacation Rental that Knutson & Associates Management is proud to represent. Hale Lani is the perfect spot to host a unforgettable Hawaii Vacation. With 4 bedrooms, and a capacity to sleep 14,...

    Pool
    FREE CANCELLATION

    $695 to $1,759/night

  24. HOUSE
    Lokelani

    Lokelani

    Hanalei, HI

    LOKELANI - (Heavenly Rose) TVNC-1226 TA189-999-3088-01 A luxury beach house close to Hanalei town and the beautiful Bay. This tastefully decorated three bedroom, three bath home is truly a little slice of heaven. From the moment you enter the...

    $689 to $919/night

  25. HOUSE
    Ali'i Point 5

    Ali'i Point 5

    Kailua-Kona, HI

    Ali'i Point #5 is located at Ali'i Point, a private and gated community of 16 seaside homes with community pool and tennis court. Central A/C throughout. Main floor has living room, dining room, kitchen, half bath, and master king bedroom with en...

    Pool

    $668 to $846/night

  26. HOUSE
    Ainamalu Home 69-9242

    Ainamalu Home 69-9242

    Waikoloa Village, HI

    Come and enjoy a luxurious laid-back island living in our new home located in the beautiful new neighborhood in Waikoloa Beach Resort – Ainamalu. This gated community Ainamalu is the newest resort community in the beautiful Waikoloa Beach Resort,...

    FREE CANCELLATION

    $649 to $896/night

  27. CONDOMINIUM
    Papakea K-402

    Papakea K-402

    Lahaina, HI

    The Ultimate Island getaway awaits you at our luxury 3 bedroom, 2-1/2 bath split level condo in West Maui!  Our beautifully furnished condo has spectacular views of the ocean making it the perfect place to whale watch (during season) and sip...

    Pool Hot Tub
    FREE CANCELLATION

    $603 to $860/night

  28. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    This brand-new beautiful new 5th floor listing at the Mahana at Kaanapali boasts gorgeous views of both the tranquil blue Pacific Ocean AND the lush West Maui Mountains. This property is extremely close to the water, you can literally sit in the 5th...

    Pool Hot Tub
    FREE CANCELLATION

    $583 to $1,861/night

  29. CONDOMINIUM
    Hale Ko Olina Beach Villa Penthouse (O-1602)

    Hale Ko Olina Beach Villa Penthouse (O-1602)

    Kapolei, HI

    Enjoy panoramic ocean views from this incredible 16th floor, 3 bedroom, 2.5 bathroom penthouse at the Beach Villas at Ko'Olina! This one of a kind villa features two lanais, a gourmet kitchen with Sub-Zero fridge, Wolf oven & glass top range....

    Pool Hot Tub

    $566 to $1,668/night

  30. CONDOMINIUM
    New! Updated! Modern, Maui Beachfront with Central A/C

    New! Updated! Modern, Maui Beachfront with Central A/C

    Lahaina, HI

    Most frequently asked questions re: payments, cancellations, our home, and the area, can be answered in the property info, guest reviews, and pictures, below. We kindly ask that you read all of these details, as we offer a lot of amenities that...

    Pool Hot Tub
    FREE CANCELLATION

    $561 to $731/night