Find Your Hawaii Vacation Rental

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    Top Destinations: Hawaii Island , Maui , Kauai , Oahu, Waikiki , Molokai

    Hawaiian Island Vacation Rentals

    Hawaii vacation rental settings that range from rural charm to urban energy. Whether you’re planning a family reunion on Maui, romantic honeymoon on Kauai, or shopping spree in Waikiki, you’ll find a choice of vacation rentals that are as distinctive as the destination.

    Choose Your Experience

    Family Friendly

    Family Friendly

    We have you covered in family-friendly vacation rentals that define sun and fun in paradise! From extra space to more amenities to keep the family busy, we have the perfect rental for you and your family!

    Oceanfront

    Oceanfront

    Listen to the soothing sounds of the Pacific as you kick off or wind down your day. You can't get much closer to the ocean than these vacation rentals. Any closer, and you'd be on the sand.

    Off the Grid

    Off the Grid

    Unplug and disconnect from all the noise. It’s time to slip away, take it down a notch, and immerse yourself in the rural, unspoiled beauty of the Hawaiian Islands.

    Island Nightlife

    Island Nightlife

    Each island offers its own spin on nightlife, from trendy bars and nightclubs on Oahu to live Hawaiian music and Mai Tais on the beach on Maui. Whatever your scene, these vacation rentals are just steps from the action.

    image: halii kai resort pool at night

    Luxury

    Bask in the lap of luxury in stylish suites flaunting views so gorgeous that you’ll never want to leave. Relax the day away poolside and return to your beautifully decorated Vacation Rental to refresh and plan your evening!  

    Budget

    Budget

    Want a getaway that doesn’t take it all away? Experience the beauty of Hawaii and all it has to offer on a budget you can afford. Castle Vacation Rentals connects you to paradise for less.

    LGBTQ+ Friendly

    LGBTQ+ Friendly

    Nowhere puts you closer to Pride in Paradise action than Castle Vacation Rentals' TAG approved Waikiki Grand Hotel with LGBTQ+-friendly Hula's Bar & Lei Stand located on the 2nd floor! 

    Choose Your Destination

    Poipu Beach

    Poipu Beach

    Stay at at one of our vacation rentals on Poipu Beach, consistently rated as one of the best beaches in America, nestled on Kauai's sunny south shore. Enjoy shopping, golf, and a variety of eateries.

    Waikiki Beach

    Waikiki Beach

    From peaceful retreats at the edge of Waikiki to accommodations in the heart of this world-famous vacation hotspot, we offer an array of vacation rentals to meet your needs.

    Kapaa

    Kapaa

    Centrally located on Kauai's eastern shore just north of the famous Wailua River, this beachside town features charming shops, delicious eateries, and convenient access to Hanalei on the north shore and Poipu, Waimea Canyon, and Kokee on the south shore.

    Kailua-Kona

    Kailua-Kona

    The sunny Kona district stretches along nearly the entire west side of Hawaii Island and offers a wealth of experiences from snorkeling with sea turtles in calm Kona waters to sampling distinctive flavors of Kona coffee on the cooler upland slopes. 

    Waikoloa

    Waikoloa

    On the rugged Kona coastline of Hawaii lies Waikoloa, offering world class golf, spas, sport fishing and sailing. Our vacation rentals at Halii Kai Resort at Waikoloa and nearby Mauna Lani put you right in the center of the action!

    Kihei

    Kihei

    Located in South Maui with gorgeous views of Haleakala, Maalaea Bay, and neighboring Kahoolawe, Molokini Crater and Lanai, Kihei is a more affordable alternative to the mega-resorts in nearby Wailea and Makena. 

    Make the Most of Your Investment

    List your home with Castle Vacation Rentals Hawaii

    Experience The Castle Difference