Located on Lake Vermillion in Cook, MN, this 30-acre, two-cabin estate on the 120-acre Taylor’s Island boasts expansive lakeside decks where you and your pooch can relax together. Fido is invited to dive off the dock, chill out in rec room, and warm up by the fireplace in the gazebo gathering area when the sun starts to set. You and your pup can also go for a ride on the hydro bikes or golf cart, relax on the sandy beach, and explore the rest of the lakefront acreage on winding trails while meeting permanent residents like deer and chipmunks. Private Island Estate on Lake Vermilion sleeps 14 and welcomes dogs for free.

Despite the name, Dogatraz Island isn’t a high-security jail for naughty canines. It’s a delightful getaway just a 10-minute canoe paddle from the mainland in Hinesburg, VT. Your host will take you to the island to drop you off and pick you up when it’s time to go home. When Fido sees the picture of Lily diving into the water on the living room wall and all the other dog-centric decor, he’ll know he’s come to the right place. After exploring the island and going for a splash, use the outdoor shower to clean off muddy paws and hang your wet leash on the hooks. Dogatraz Island sleeps four people and welcomes pups for free.

One of our favorite beachfront properties, East Sister Rock Island is the most luxurious escape on our list. Located off the coast of Marathon in the Florida Keys, this tropical haven is accessible by a complimentary Carolina Skiff. Get out on the water with your hound during the day, then hang out on the veranda and listen to the waves lapping against the manmade moat when the sun sets. East Sister Rock Island sleeps eight guests and has no pet fee.

Check three items off Fido’s bucket list on one trip at this Emerald Isle tiny house, where you can experience tiny living, a glamping adventure, and a private island on the same vacation. Guests at this pack-in/pack-out location in Swansboro, NC, are invited to switch off from modern life and get back to nature. The private island comes equipped with a 40-foot dock, a rustic tiny home and a safari tent for glamping fun. Hop in one of the four complimentary kayaks provided to explore the waterway surrounding the island and visit the nearby, pet-friendly Emerald Isle Beach. In addition to free kayak rentals, the host’s licensed captain can drop you off and pick you up when it’s time to check out. The Emerald Isle tiny house sleeps six and welcomes dogs for free.

Rustic Private Island Cabin on North Twin Lake offers a unique stay for guests who own a boat to get to and from the private island. Paddle together in the waters of the lake, use the grill to prepare Fido’s fresh catch from the day, and roast s’mores by the fire pit before retiring to the rustic cabin for the night. The rental is totally off the grid, but has excellent cell phone and wireless connectivity. In addition to bringing your own boat, you’ll need to bring your own linens (towels, sleeping bags, bed linens) and drinking water. Located in Indian Township, ME, Rustic Private Island Cabin on North Twin Lake sleeps six and allows dogs.

Sharp’s Island is the only legal camping destination in the city of Richmond. Bring your tent and camp on the beach or among the trees of the forested interior of the island. This one-of-a-kind spot in Virginia’s capital offers unrivaled angling opportunities on the James River. Guests must paddle by kayak to get there, but if you don’t have your own, you can rent one from RVA Paddlesports. Sharp’s Island sleeps 12 people and has no pet fee.

Surrounded by a side channel of the Snake River, Juniper Island in Rigby, ID, offers 10 acres of land and a log cabin for a private island paradise. Hang out on the three decks and enjoy views of the surrounding cottonwood forest, where the only sound is gushing water and abundant wildlife, including bald eagles, moose and deer. Shoot hoops on the custom-designed basketball court, play ping pong or air hockey in the game room, grill out supper on the Traeger grill, and enjoy a soak in the hot tub while stargazing. Dogs who like islands but hate water will be ecstatic to learn that the retreat can be accessed by a bridge. The best time to visit is during the fall, when the island’s trees turn a stunning array of colors. Juniper Island sleeps 12 and welcomes dogs.

The worst part about a lake trip is having to go home at the end of the day. Why not stay on the lake instead? Located in the heart of Lake Winnipesaukee in Alton, NH, Island Camp offers groups the choice of three cabins. Once you settle in, head out to explore the natural surroundings on the two-mile walking path, cast off into the lake from the dock, and doggy paddle in the picturesque swim area near the shore. You’ll need your own boat to get here. Island Camp sleeps eight and welcomes dogs for free.

If you love nothing more than putting with your pooch, set sail for Round Island Retreat. This private island can be found at the center of Sylvan Lake in Rome City, IN, and is home to its very own putting green for you to practice your swing. After one too many misses, don’t just admire the 360-degree views of the lake; get out on the water. The retreat offers access to the lake from two dock locations and includes exclusive access to a pontoon boat. Round Island Getaway sleeps 14 and welcomes pets for no additional fee.

Home to one of the oldest cottages in the 1,000 Islands, Whiskey Island welcomes you and your pooch to experience a piece of history. First built in 1875, this island lodge in Clayton, NY, has been the backdrop for vibrant sunsets and vast stargazing sessions on the St. Lawrence River for generations. Explore just over three acres of land with your pooch, swim, or fish in the river together, and feel the rejuvenating properties of the isolated home. In addition to the grand lodge with a library and five porches, other buildings include a guesthouse, boathouse and skiff house. You’ll need your own boat or can take a water taxi to get here. Whiskey Island sleeps 15 and allows two small dogs.