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
    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

  2. HOUSE
    Home of the Hula Moon

    Home of the Hula Moon

    Waimea, HI

    Stately and serene, Hula Moon sits on one of the most beautiful properties in Puako. Located at the quiet end of the road, you will enjoy year-round sunsets and privacy. As you enter through the gates, lush tropical plantings enhance the large...

    Pool

    $1,876 to $2,662/night

  3. 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

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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

  9. 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

  10. 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

  11. 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

  12. 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

  13. 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

  14. CONDOMINIUM
    Wailea Elua Unit #1403

    Wailea Elua Unit #1403

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $931 to $1,459/night

  15. CONDOMINIUM
    Makena Surf Resort, #G-304

    Makena Surf Resort, #G-304

    Makena, HI

    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and...

    Pool

    $898 to $1,235/night

  16. CONDOMINIUM
    Makena Surf Resort, #B-204

    Makena Surf Resort, #B-204

    Makena, HI

    A note from the owner: Welcome to our piece of paradise. We love time at our Makena Surf unit. Uniquely located on the second floor of B building, we see the spectacular beach and ocean view up-close-and-personal from the privacy of the second...

    Pool

    $773 to $1,319/night

  17. HOUSE
    Honu Ohana House 69-1757

    Honu Ohana House 69-1757

    Waimea, HI

    This is a big, fun beach house with several areas to enjoy as a whole group or to tuck away from the rest of the group’s festivities for some private time. Perfect for multi-generational families and/or extended family with friends. The home is...

    Pool

    $756 to $1,585/night

  18. CONDOMINIUM
    Wailea Elua Unit #0908

    Wailea Elua Unit #0908

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $724 to $1,065/night

  19. HOUSE
    Hale Lokahi

    Hale Lokahi

    Waialua, HI

    Hale Lokahi - House of Peace and Serenity - This home is located in one of the best kept, secret neighborhoods on the north shore. Right on a white sand beach, this family-owned house is perfect for your vacation in paradise.. This 4 bedroom, 2...

    $683 to $992/night

  20. 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

  21. 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

  22. 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

  23. CONDOMINIUM
    Royal Mauian Unit #302

    Royal Mauian Unit #302

    Kihei, HI

    Royal Mauian is a unique six story oceanfront property located in South Kihei offering unobstructed views of the clear blue Pacific. The property and adjacent Kamaole Beach together provide excellent locations for stunning sunsets, snorkeling,...

    Pool

    $560 to $702/night

  24. CONDOMINIUM
    Makena Surf Resort, #C-102

    Makena Surf Resort, #C-102

    Makena, HI

    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and...

    Pool

    $538 to $926/night

  25. CONDOMINIUM
    Ko Olina Beach Villa (O1105)

    Ko Olina Beach Villa (O1105)

    Kapolei, HI

    This 3BD Penthouse Beach Villa is located on the 11th floor of the Ocean Tower and is 1,734 sq ft of luxury. It features ocean views the kitchen and living/dining area. The master bedroom has a private lanai with views of the golf course and...

    Pool Hot Tub

    $520 to $1,668/night

  26. CONDOMINIUM
    Wailea Elua Unit #0202

    Wailea Elua Unit #0202

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $494 to $1,065/night

  27. 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...

    $485 to $652/night

  28. CONDOMINIUM
    Wai'ula'ula D201 Condominium

    Wai'ula'ula D201 Condominium

    Waimea, HI

    Welcome to Wai'ula'ula at the Mauna Kea Resort! Your vacation will truly be one to remember in this beautifully decorated condominium in the gated community of Wai'ula'ula, located on the Hapuna Golf Course. This recently built luxury development...

    Pool
    FREE CANCELLATION

    $481 to $1,174/night

  29. HOUSE
    Sands Of Kahana 315

    Sands Of Kahana 315

    Kahana, HI

    Take advantage of this opportunity to stay and indulge at a beachfront, luxury condominium with 100% ocean views from the living room, bedroom and lanai. Beautiful 2 bedroom, 2 bathroom, ocean front corner unit that provides stunning ocean views...

    Pool Hot Tub

    $478 to $531/night

  30. HOUSE
    Sands Of Kahana 234

    Sands Of Kahana 234

    Kahana, HI

    Enjoy views of Molokai and Lanai in one of nicest remodeled corner units in the Sands of Kahana. This air conditioned 2 bedroom 2 bath unit with two lanais is one of the most spacious waterfront units in Maui. From the front Lanai you’re so close...

    Pool Hot Tub

    $478 to $531/night