
Family-friendly holiday rentals in Wisconsin
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Top-rated family-friendly rentals in Wisconsin
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Tiny on the River
According to Forbes, Escape makes "the most beautiful tiny houses in the world". Ours is perched near our home above the Black River. It's a quiet neighborhood just minutes from the interstate, parks, trails, and our vibrant downtown with cafés, shops, and great restaurants. Enjoy privacy and breathtaking views from the enormous windows or the cozy daybed on the porch! Deer, beaver, eagles, and more make frequent cameos as the seasons paint shifting riverscapes and astonishing sunsets. *No Pets

Nature’s Nest
Unwind and immerse yourself in nature at this cozy cabin overlooking Timber Coulee Creek. Large living room windows and a spacious deck provide you with a bird’s eye view of the rippling river and many types of wild life. Deer amble through the property; eagles soar and keep an eagle eye on everything. Turkeys, squirrels, coons, and myriad of birds go about their business in this serene environment. Trout fishing is an excellent pastime for those who care to cast a line. Rest, at Nature’s Nest.

Lakeside Loft, Roof Deck + Sauna
Wanderloft, designed by architect David Salmela, combines modern Scandinavian design with the natural beauty of Wisconsin's Northwoods. Located on one of Vilas County's highest points, this cabin provides stunning 360-degree views from various levels overlooking Manuel Lake and 9.4 acres of land. Beyond its striking design, Wanderloft is defined by its profound sense of peace and quiet - where natural beauty and thoughtful architecture create space for rest, creativity, inspiration, and renewal.

Cozy Log Cabin in the Woods
Adams County TRH License #7333 Welcome to the Lucky Dog Cabin! Nestled in the trees, our charming log cabin is located 25 minutes North of the Wisconsin Dells and less than 10 minutes from Castle Rock Lake, Wisconsin River, and Quincy Bluff State Park. Come relax, unplug, and get away from it all. Enjoy the fresh air, starry nights, and peaceful nature sounds. Our 9 acre property offers a beautiful trail that leads to gorgeous sunset views, through the forest. A true nature-lover's paradise!

Seeley Oaks A-Frame | Couples Winter Getaway
This is a cabin-in-the-woods experience! The Seeley Oaks A-Frame is our slice of the peaceful Northwoods experience. It's on 40 private, tranquil acres (no neighbors!) with great access to all the Hayward-Cable area has to offer. It's small - intended for two adults, with the option of 2 addtl kids. It's a total of 700 sq ft, with a queen bed in the loft, in-floor heat, full kitchen, and washer and dryer. Less than 2 mi from Highway 63, 8 mi from Cable, and 10 mi from Hayward. IG: @Seeleyoaks

Cool quiet country cabin on boulders and 120 acres
Funky, tidy 23 year old country cabin on 120 acres of farmland & woods in a private, quiet rural setting. It's cozy, 950 sq ft, built with stone and wood. Open concept with a two story fireplace, porch fireplace, firepit, and open loft for sleeping (1 bed), with spiral stairs, lots of windows, walnut floors and trim, oak beams and pine kitchen tops. Shower is big and open, with doors opening to a back deck for outdoor showering. Beautiful covered porch overlooking rolling meadows and woods.

Quiet Seclusion at Trade River Retreat Cabin
Remote, tranquil, quiet and exceedingly private getaway right on the banks of a protected river, only 1.5 hours from the Twin Cities! Even the beautiful drive there is relaxing. Enter a world of peace and calm deep in the woods. Make delicious meals in a well-stocked modern high-end kitchen, play in the river, relax in the sauna or enjoy a bonfire. This is not your typical cabin but a spiritual eco-oasis with a unique eclectic blend of modern, rustic, Native American and Japanese aesthetic.

Scenic, Serene Lakefront Cabin — Wood Stove
Nestled on the tranquil Grass Lake, your cozy cabin retreat awaits! Whether enjoying yard games, the crackling bonfire, or the snug embrace of the wood stove, this space is thoughtfully crafted for your next family getaway or peaceful solo escape. Bask in the breathtaking lakefront views from the dock, deck, or four-seasons room. Immerse yourself in a space designed to foster connections and spark creativity. We welcome you to join us and create your own beautiful memories at the cabin.

Secluded Cabin with Sauna
Place yourself in nature. Put down your phone and pick up a book. Clear your mind, focus on your breath, connect with your inner self. Sleep like you’ve never slept before accompanied only by the sound of owls and wind in the pines. The Belden Farm offers land that is a true retreat. Enjoy the privacy and quiet of our cabin in the woods. Extensive, well-maintained trails for hiking, skiing or Fattire biking lead you through towering hardwoods, cathedral white pines, and golden meadows.

Snowshoe Creek & Little Wood Lake Tiny House
New 520 sf 'not too tiny' house on 20 wilderness acres. Year 'round fun. Dog friendly. RV & EV plug. Firepit. Your Snowshoe Creek and Little Wood Lake trails. Free canoe, kayak, paddleboat. $40/day mini-pontoon boat. Fishing. Internet. WiFi. AC. Gas Fireplace. Sleep by Number. Lovely bathroom. New gas stove. Ice maker. 2 TVs. 3 towns + Burnett Dairy/Bistro, 4 golf courses, DQ to fine dining, mini-golf, antiquing, multi-theater, Siren beach & 'Music in Park'. Wildlife! You'll return.

hot tub and sauna on 5 private acres
Looking for a cozy winter retreat? Experience the Bird House, a tranquil Scandinavian-inspired private woodland paradise. Melt away stress in the hot tub and infrared sauna as you take in peaceful views of the meadow. Explore snowshoe and cross-country ski trails nearby in the scenic Kettle Moraine. Stream your favorite movie on the projector near the fireplace or unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee.

The Raven
Nestled in a quiet, wooded neighborhood, The Raven boasts all the comforts and conveniences of home while offering the peace that only comes when you get away from it all. We're just ten minutes from charming restaurants, local shops, the chain of lakes, and only five minutes from Hartman Creek State Park and the Ice Age National Scenic Trail. Whether to relax, to recharge, or to explore, welcome to your modern escape to the woods. Welcome to The Raven.
Popular amenities for Wisconsin family-friendly rentals
Family-friendly home rentals with a hot tub

SevenTwenty: Staying In Never Felt So Good

~Driftwood Haven Cottage ~

New Hot Tub Nov 2025, Firepit, Eco-Friendly

Sunset Sanctuary- with outdoor hot tub

The Loch at WhiskyWood, secluded cabin + hot-tub

Big R's Retreat Secluded and located in Nature

The Cottage at Streamwalk

Nordic Lake Cabin : Sauna/Hot Tub/Pontoon Rental
Family- and pet-friendly home rentals

Star-gazing, quiet privacy in the forest

Driftless Trout Cabin - Hillsboro, Wisconsin

Romantic Forest Cabin, Sauna, Trail to Beach

Sasquatch Shores: Cozy Lakeside Cabin on Star Lake

Sölveig Stay: Shipping Container with Nordic SAUNA

The Acorn of Little Sand Bay Dog Friendly

Pet Friendly Antique Schoolhouse with Fenced Yard

Cool, Roomy, Scenic Country Art Studio
Family-friendly home rentals with a pool

Lake Arrowhead Brown Bear Lodge Sand Valley GOLF

River Run Ridge - HOT TUB- river view - sleeps 14

COZY, Pickleball, Fireplace, Devils Lake

The Landis, elegant condo w/ king bed & fireplace!

LG Quaint Condo on Lakeshore Dr.

Relaxing Villa with Amazing Amenities!

The Wanderlust at the Sunset Cove

Luxurious Chula Vista Retreat
Destinations to explore
- Rentals with a home theatre Wisconsin
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- Rentals with a fireplace Wisconsin
- Rentals with a hot tub Wisconsin
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- Family-friendly rentals United States




