Vacation Ideas

Hawaii Vacation Rentals for Everyone

Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

    • Search

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

    Family Friendly - Family in Pool

    Family Friendly Vacation Rentals

    Pack your board shorts. But forget the board games. We have you covered in family-friendly resorts that define sun and fun in paradise! From access to kids clubs to restaurants where keiki (children) are treated like kings, Castle pampers ohana (family) with the royal treatment! Snorkel at Kauai’s Lydgate Beach Park before heading home to barbeque at Kaha Lani Resort. Or follow a surf lesson with lounging by the pool as the kids continue to splash away at Maui’s Kamaole Sands Resort.

    Show Me (400+)

    Trending Vacation Ideas

    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!  

    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.

    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.

    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! 

    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.

    Active Lifestyle

    Active Lifestyle

    If keeping up with your workout is a must while on vacation, these vacation rentals include on-site fitness centers or workout equipment for your convenience, such as this fitness center with an ocean view at Halii Kai at Waikoloa.  

    Oceanfront Digs

    The ocean is your magnet and you've got choices to make. It's time to figure out which Hawaiian Island fulfills your oceanfront attraction and which vacation rental will you choose to stay at? From mellow Kanaloa At Kona on Hawaii Island to mega-energy Waikiki Shore, Castle presents a menu of oceanfront and beachfront retreats where Pacific sites and sounds never let your forget that you’re in paradise. Indulge with suites that flow from a ground floor lanai onto the sand, or elevate the view to peak over swaying palms as you toast sunset on your private lanai.   

    Check it out (332)
    Poipu_Shores_2DOF_205A_LanaiView_1

    Top Vacation Rental Destinations 

    Poipu Beach

    Poipu Beach

    Snorkel, swim, boogie board or surf on Kauai at Poipu Beach theTravel Channel has lauded as America's Best Beach. Stay at Castle Vacation Rentals at Kiahuna Plantation, Makahuena at Poipu and Poipu Shores!

    Waikiki Beach

    Waikiki Beach

    Castle Vacation Rentals at Waikiki Shore and Waikiki Grand are located on opposite ends of Waikiki Beach and serve as perfect bookends for this world-famous hotspot that was once a playground for Hawaiian royalty. 

    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. 

    Molokai

    Molokai

    If you seek refuge from modern life and you want an unforgettable adventure the island of Molokai is the choice for you. Castle Vacation Rentals at Molokai Shores will instantly allow you to unwind and take it all in!

    Halii_Kai_3OV_11E_LanaiView1

    Stay on the Fairway

    Playing into each island’s distinctive landscape, Hawaii’s 70-plus golf courses roll out with stunning ocean side water hazards, greens lined with black volcanic rough and ample sand traps, naturally. Beyond creative designs, golfers also find challenge in attention-grabbing scenery that’s always above par. Hawaii Island is a hit with Kona at Kanaloa’s prime location on Kona Country Club. Or tee-off at Waikoloa, where you can replay the day with tropical libations on your Halii Kai lanai that fringes fairways you just conquered. 

    Show Me (83)

    The Active Traveler

    PoipuBeachAthleticClub_TennisCourt.jpg

    Tennis Anyone?

    Love a little friendly competition? Enjoy on-site Tennis at Castle Vacation Rentals Kamaole Sands, Kanaloa at Kona, & near-by at Kiahuna Plantation-Poipu Beach Athletic Club. Plenty of courts & raquets for all levels. 

    Fitness Rooms

    Fitness Rooms

    Maintain workout regimes at a fitness center or gym located right at your Vacation Rental, Some like Halii Kai (pictured above) include an ocean view! So go ahead & enjoy yourself on vacation - your workout dedication will not waiver!

    Kona Ironman

    Kona Ironman

    Stay close to the action at Castle Vacation Rentals Kona Reef, Kona Bali Kai or Kanaloa at Kona. Marvel as diehards swim 2.4 miles, bike 112 miles and run 26.2 miles! Don't miss an exciting minute of jaw dropping athleticism!

    Honolulu Marathon

    Honolulu Marathon

    We'll put you right next to the finish line! What better way to cap off a 26.2-mile race than kicking off your shoes in your room at Waikiki Grand Hotel, relaxing, and then heading out for celebratory food and drinks?

    HaliiKai_FitnessCabana.jpg

    Pride Festival

    Hawaii is a celebration of color, diversity and friendliness. Our TAG approved Waikiki Grand Hotel is across from the Annual Pride Festival and Parade in October. 

    Love Nests 

    Nothing says romance quite like a cozy vacation rental for two in a tropical setting and we've got you covered. Cascading waterfalls and sundrenched sands, couples are hard-pressed to dodge Cupid’s arrow when staying with us. Dial back the pace and turn up the adventure, it’s time to share the love–start with an early morning set of tennis, relax poolside, horseback ride through private ranchlands or just stroll hand-in-hand along the beach at sunset, stay with Castle & be close to it all!

    Let's go (189)
    Ke_Nani_Kai_1OV_208_Molokai_Sunset

    Special Offers Email

    Sign up to receive 15% off your next stay

    Make the Most of Your Investment

    List your home with Castle Vacation Rentals Hawaii

    See What Castle Can Do For You