Cool, quirky, and totally bookable vacation homes
From cozy cabins to bold beach houses, these one-of-a-kind homes are anything but average.
Updated in 2025
Updated in 2025
Looking for a stay that’s anything but ordinary? You’re in the right place. We’ve rounded up 16 vacation rentals across the country that bring the charm, the character, and the wow factor. Whether it’s a retro A-frame in the woods or a beach house with bold design vibes, these homes stand out—in the best way. Ready to scroll, swoon, and maybe even book your next getaway?
Ever imagine having a private island to yourself? Bask in water views from almost every room and almost every direction during your stay in this luxurious and unique vacation home, resting on its own little island in the middle of Alligator Bay, just north of Topsail Island. Cool off with a dip in the private swimming pool, catch up on a good book while lounging on the sun deck, and after dinner (or before—we won’t tell), gather family and friends for s’mores around the outdoor fire pit.
Just outside of the Great Smoky Mountains National Park, your traincation awaits. Train enthusiasts, youngsters, and those young-at-heart are welcome aboard this 1916 CSX caboose-turned-tiny home, fully decked out with a replica ticket stand, modern amenities, and two cozy bedrooms. This unique vacation rental rests in the heart of the Smoky Mountain action, only 1.6 miles from Dollywood and less than a mile from the Rocky Top Mountain Coaster. Head out on a day of hiking or amusement park fun and wind down the night by the fire pit or hot tub.
Perched atop eight secluded acres on the North Coast, Cantus Cove Estate offers uninterrupted ocean views and the soothing sound of waves to wake you each morning. Relax in Adirondack chairs as the sun sets over the bluff, watch for whales in Caspar Cove, and take in the crisp, salty air as deer roam the peaceful, park-like grounds.
Sneak away to a romantic tropical retreat for two. This treehouse-style getaway, just steps away from the beach, ensures you’ll never miss a relaxing ocean breeze. Add some freshly picked tropical fruit to your breakfast before you head out for a day of horseback riding by the ocean. Tucked away from the busy streets, with nearby nature tours, waterfall hiking trails, and jungle wildlife, you’ll feel you have this private corner of Costa Rican paradise to yourself.
Meet the best place to spend your snow days. This luxury-meets-cozy vacation rental promises winter thrills for skiers and non-skiers alike. In the morning, wake up to snowcapped mountain views of Breckenridge and get ready to start your day, whether that’s hitting the slopes (just step out the door to the base of Peak 8) or never leaving the massive 14-person hot tub. Warm up with some time in the steam room, a dip in the soaking tub, or cozying up by any of the home’s five fireplaces. End your evenings by challenging your little ones to a competition in the game room or with a coveted après-ski spot by the stone fireplace, watching the snowflakes dance outside.
Step out on Boxer Bay’s large deck and it might be a challenge to pull yourself away from watching the waves. Whether on a romantic retreat or seeking some quiet time, you’re sure to find it in this vacation home’s unique design, as its curved structure frames the dramatic Oregon coastline as the focal point. The home’s tasteful interior suits the soothing ocean atmosphere, where you can ease back, soak in the hot tub, and savor some well-deserved R&R. Though you can feel free to indulge in the seclusion, there’s WiFi and nearby restaurants and cafes to keep you connected.
Nestled on the shores of Pamlico Sound, Croatan Ridge is a secluded retreat where luxury and nature blend seamlessly. Every moment here is pure magic, from the sweeping sunrises over the Atlantic to stunning sunset views stretching across Hatteras Island and the calm waters you can explore by kayak or enjoy from the shoreline.
A vacation of the noblest kind awaits. Perched on Schweitzer Mountain, this Medieval castle invites you to step back in time and live the fairytale you’ve always dreamed of. Complete with vaulted ceilings, stained glass windows, a stone fireplace, a hot tub, Medieval decor (including armor, swords, and statues), a proper knight’s table, and a rooftop dragon, you’re in for an enchanting experience as you explore Northern Idaho or ski the slopes at nearby Schweitzer Mountain Resort. Open a bottle of mead with dinner, make paper crowns for your kids, and savor the mountain views from the hot tub. Add a touch of magic to your family vacation or romantic getaway in this cool rental.
Outdoor adventurers, meet your perfect bucket list match. Deep in the lush jungle of Costa Rica, indulge in a tropical off-grid getaway over 160 acres of this mini-eco compound. From three treehouse-like bungalows, you’ll be able to swing into one activity after another, between hiking the walking trails, sampling the fruit trees, mixing drinks at the bar, swimming in the private pool, or taking a dip in any of the surrounding natural pools and waterfalls on the property. This one-of-a-kind vacation home is the ideal place to unplug and unwind, as there’s no WiFi, but plenty of opportunities to reconnect with nature while spotting tropical birds and jungle animals. As a bonus: during your stay, keep a running tally of how many decorative sloths you find.
Visually and scientifically intriguing, this vacation home’s prime location and secluded nature make it a fantastic backdrop for your next mountain getaway. Not only does it rest on a private wooded acre on the edge of Glacier National Park, but you’ll find that even the architecture is engineered for easy relaxation. Geodesic domes are built to promote seamless air circulation and keep temperatures even throughout the home—plus, they add a unique cool factor to any vacation. After hitting the nearby ski resorts or exploring the national park, come back to cozy up by the fireplace and tell stories around the outdoor fire pit.
Discover the perfect blend of island luxury and outdoor adventure at this stunning waterfront retreat in Marathon. Nestled on the bayfront of Grassy Key, this recently updated, pet-friendly home offers a private beach, a sparkling pool, and breathtaking ocean views while living up to its name by being a boater’s dream, a nature lover’s retreat, and a sun-seekers paradise all in one.
Hidden away on Florida's Gulf Coast, this Casey Key estate offers a tranquil escape immersed in natural beauty. Here, you can savor breathtaking water views from every room, spend blissful afternoons on your private beach access, and reconnect with loved ones in the luxurious outdoor living areas featuring a summer kitchen, pool, spa, and dock. With impeccable finishes, multiple living spaces, and amenities like a home theater, this architectural masterpiece provides the perfect blend of relaxation and indulgence for an extraordinary vacation experience.
Perched on Schweitzer Mountain, this handcrafted masterpiece, known as the Schweitzer Castle, offers an experience that’s equal parts enchanting and relaxing in an actual living stone castle. And while the castle may feel worlds away or from a bygone era, fear not—its four levels boast a blend of modern amenities and old-world features, ensuring a comfortable and memorable stay.
What's more, the Schweitzer Castle can be booked alongside Chateau De Mesuline as one reservation, allowing guests to live out their renaissance dreams in Idaho.
Welcome to pure coastal luxury in the keys.
This Gulf-front Florida escape combines luxury and seclusion, featuring a private beach and heated saltwater pool perfect for group getaways. Beyond the pristine shoreline, guests can explore nearby wildlife refuges or venture to Key West's attractions just 18 miles away. With provided paddleboards, kayaks, and beach gear, plus space for everyone to unwind, it's an ideal base for both adventure-seekers and relaxation-lovers.
Tucked away in the Smoky Mountains, this cabin is more than just a getaway—it’s an experience. Whether you're craving relaxation or non-stop entertainment, you’ll find it here. Wake up to stunning mountain views, spend your days playing putt-putt on your private mini golf course, or challenge your group to a game of foosball, bowling, or arcade classics.
If you've ever dreamed of having your own private bowling alley on vacation, this Timbertown Lodge spares no details and abides by your every need. Including the fully functioning four lanes, your reservation pins down space for up to 40 guests, endless entertainment like access to pickleball courts and a pool table, and an additional cottage for more space. What's more, it's also a rolling distance from the East and West Twin Lakes.
