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Family-friendly vacation rentals in Columbia County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Columbia County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A cottage is nestled within a wooded area, featuring light-colored siding and a green roof. A wooden deck leads to the entrance, surrounded by autumn leaves and natural landscaping. Windows allow natural light to illuminate the interior, creating a warm and welcoming exterior.

Cottage in Poynette

4.96 out of 5 average rating, 238 reviews

Lake Wiscosnin Cozy Cottage

Relax and unwind at this cozy cottage on the Wisconsin River with fantastic views. Enjoy the park right across the street with fishing, a picnic pavilion, beach and playground for your kids. Public boat launch is only a block away. Full laundry and eat in kitchen features quartz counter tops and makes you feel like you're home away from home. Many local restaurants and bars within driving distance, as well as wine tasting and 2 ski resorts. Keurig and a propane grill provided. CableTV and Wifi

Top guest favorite

Home in Baraboo

4.96 out of 5 average rating, 129 reviews

Cottage Near Devil's Lake

Perfect Location! Under ten minutes to almost everything. Our cozy and romantic getaway is nestled in the scenic Baraboo Bluffs, just minutes to Devil's Lake, Devil's Head Resort, Historic Downtown Baraboo, wineries, distilleries & more. Take the picnic set to Devil's Lake or Parfrey's Glen, then relax on the patio for smores and yard games around the fire pit. Finish the evening snuggled up with wine & vinyl on the player. We have ample parking so bring the boat, we'd love to help you getaway.

A spacious dining area features a wooden table set for six, adorned with lace placemats and a floral centerpiece. The open layout leads to a cozy living room, highlighted by comfortable seating and large windows allowing natural light to brighten the space.

Home in Portage

4.95 out of 5 average rating, 113 reviews

Grandma's House: Coming Soon-Fall Colors!

Welcome to Grandma's House, a single level home nestled in the beautiful hills of Caledonia, between Portage and Baraboo. Three bedrooms, sleeps 8, full kitchen, dining room, living room and an attached 2-car garage. Just 4 miles from I90/94, Grandma's House enjoys easy access to Portage, Baraboo and Wisconsin Dells. 2023 renovations include, new vanity mirror in bathroom, new queen hide-a-bed with memory foam mattress (no bar at the back), and new queen bed with pillow- top mattress.

A welcoming living area features a large flat-screen TV mounted on the wall, adjacent to a modern electric fireplace. Dark leather seating is complemented by square ottomans. Natural light enters through the sliding glass door, leading out to a private patio.

Condo in Wisconsin Dells

4.84 out of 5 average rating, 296 reviews

Williamson Family Condo at Lighthouse Cove

NO SMOKING Upgrade to our Noah's Ark package after booking! This ground floor unit at Lighthouse Cove on Lake Delton is located in the heart of the Dells. Enjoy access to our private beach, in & outdoor (seasonally) pools w/ hot tubs, and convenient parking. With just a 5-10 minute walk to Noah's Ark, the older kids can wander to and from while you take a much-deserved time out. The sidewalk in front of the condo goes nearly around the entire lake for you morning exercise types.

A serene lakeside view is captured, featuring calm waters reflecting the sky and surrounding greenery. A sandy beach is visible in the foreground, complemented by a large tree providing shade. Soft clouds drift across the blue sky, enhancing the tranquil atmosphere.

Guesthouse in Poynette

4.9 out of 5 average rating, 255 reviews

Simple Cabin*Lake View rustic cabin in rural WI

The Simple Cabin on Lake Wisconsin is a simple and clean space. It would be ideal for an individual or couple who are enjoying the beautiful outdoors by day, and would like a bed by night. It is 350 sq ft for the entire cabin consisting of bedroom, small full bathroom, and living area. You will enjoy 180 degrees of across-the-water views. It's a great hub for hiking with the following all within 15 - 35 minutes: Devil's Lake, Parfrey's Glen, Gibralter Rock (ice age tr) & Mirror Lake.

The cabin's exterior features a sloped roof and a wrap-around deck, surrounded by lush greenery and colorful flowers. Large windows offer glimpses of the interior, while tall trees provide a natural backdrop, emphasizing the cabin's mid-century architectural style.

Cabin in Merrimac

4.91 out of 5 average rating, 205 reviews

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!

Top guest favorite

Home in Merrimac

4.98 out of 5 average rating, 110 reviews

Real Christmas Tree Farm! Devil's Lake nearby

Get lost in nature and stay where the magic grows on a real Christmas tree farm! Situated on rolling hills below the Baraboo bluffs, this 125 acre farm and nature preserve has several miles of hike/bike/ski trails, a private lake and two creeks. Modern home in a quiet rural neighborhood. Easy drive on beautiful country roads to the many attractions in the area--less than 10 minutes to Devil's Lake State Park, Lake Wisconsin as well as Devil's Head & Cascade ski areas.

The image captures a serene view of a resort building reflected in a calm pond, surrounded by lush greenery. Tall grasses and reeds frame the foreground, while soft pastel hues of sunset illuminate the sky, adding a tranquil ambiance to the scene.

Guest suite in Wisconsin Dells

4.85 out of 5 average rating, 549 reviews

Spacious 2 Bedroom - 8 Complimentary Park Passes!

Welcome to Wisconsin Dells and the city of Baraboo, a popular vacation playground best known for its beautiful river scenery, endless entertainment options and larger-than-life water parks. Inside the Wilderness Territory a theme park where family fun reign supreme is a top ranked indoor and outdoor water park. You can also find some excellent shopping, visit wineries for tastings, practice your swing on local golf courses, and win big at Ho-Chunk Casino.

A cabin is situated on a grassy area by Park Lake, with tall trees providing shade. A small dock extends into the water, and a modest boat is visible nearby. Nearby, a picnic table and fire pit are set up, creating a leisure-friendly atmosphere.

Guesthouse in Pardeeville

4.85 out of 5 average rating, 118 reviews

Park Lake Cottages in Pardeeville Wi

A little slice of heaven right on Park Lake in Pardeeville, WI. Located just one mile from downtown Pardeeville, thirty miles north of Madison and roughly thirty miles east of Wisconsin Dells. This is a 3 bedroom cabin where you can enjoy campfires, fishing, swimming, and boating from the piers. Also, the sunsets do not disappoint! Local attractions include; dining at The Caddy Shack or The Upper Crust and be sure to visit Carol's Cones for desert!

Top guest favorite

An outdoor patio area features a black fire pit positioned on a concrete surface. Surrounding the fire pit are various seating options, including metal chairs and tables. The backdrop consists of a two-story building with balconies and greenery, complementing a bright, blue sky.

Apartment in Merrimac

4.94 out of 5 average rating, 130 reviews

Perfect for all Seasons, Top Amenities close by!

Parfreys Glen, Devil's Lake, Devil Heads Resort....We are right next to all of these very popular destinations! A few are even within walking distance! Located on just under 3 acres we have a beautiful home here in the country that we call the Chateau. Below us we have added a brand new, 2 level, spacious apartment. The apartment features a full bathroom on each level as well, a full kitchen and a deck with a spectacular view to relax and unwind.

Apartment in Baraboo

4.87 out of 5 average rating, 282 reviews

Orchard Prairie B&B

Welcome to my home - Orchard Prairie Air B&B! This unique space was built by an amateur pilot, "MacGyver-Type," Renaissance Man roughly 30 years ago. It is set on 38 acres of pristine Wisconsin Land and is perfect for nature lovers and "Glampers" looking for the great outdoors with the comforts of home. It is a "rustic-industrial" oasis in the heart of South Central Wisconsin, steps from Devils Lake and miles from Baraboo and the Wisconsin Dells.

Top guest favorite

A spacious outdoor porch is equipped with comfortable seating arranged around a central coffee table. A gas grill is positioned nearby, and decorative cafe lights add a cozy ambiance. Lush greenery surrounds the area, enhancing the inviting outdoor space.

Apartment in Wisconsin Dells

5 out of 5 average rating, 104 reviews

Downtown! Updated cozy unit. Firepit*Porch*Patio!

Welcome to DELL-ightfully Downtown Dells! This 1 bedroom downstairs unit, being designed with your utmost comfort in mind, also boasts 2 separate outdoor spaces, so you may never want to leave! All of this PERFECTLY located just one block off of the Downtown Strip. And because we want you to focus on enjoying yourself, we provide our guests with everything we can think of and more, and not just for your first night, but for your ENTIRE stay!

Vacation rentals for every style

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Popular amenities for Columbia County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An inviting outdoor space is illuminated with string lights at night, featuring a hot tub and several chairs for relaxation. The home's large windows reveal warm indoor lighting, while the surrounding trees contribute to the serene atmosphere.

Home in Poynette

5 out of 5 average rating, 4 reviews

Secluded Luxury Escape: 50 Acres | Hot Tub | Sauna

Top guest favorite

A spacious kitchen area features a stone fireplace and modern appliances, complemented by wooden beams overhead. Four bar stools line a granite island, with a cozy armchair nearby. Natural light streams through large windows, illuminating the warm wood and stone details throughout the space.

Chalet in Baraboo

4.92 out of 5 average rating, 38 reviews

The Baraboo Chalet tucked in a canopy of trees.

Top guest favorite

A spacious log home is showcased, featuring large floor-to-ceiling windows that illuminate the interior. The fenced-in pool area is surrounded by landscaped gardens, with lounge chairs positioned near the water. Lush greenery and trees create a serene backdrop for the property.

4.98 out of 5 average rating, 52 reviews

Modern cabin with pool and Hot Tub!

A spacious family room features a cozy seating area with a gray sofa and patterned armchair. A wooden dining table with four chairs is positioned nearby. The room is brightened by large windows and includes an electric fireplace beneath a mounted television.

Condo in Wisconsin Dells

4.89 out of 5 average rating, 44 reviews

Dells Lake Lookout - Lake Access with Boat Slip

A modern multi-level home is shown from the exterior, with a large deck extending from the second floor. A swimming pool is visible in the foreground, surrounded by a grassy area. The backdrop features a wooded landscape under a clear blue sky.

Home in Portage

5 out of 5 average rating, 11 reviews

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

Top guest favorite

A well-lit living area features a combination of comfortable seating, including a brown leather couch and a cozy armchair. A round wooden coffee table sits centrally, surrounded by an area rug, while decorative wall art and a clock enhance the space.

Home in Baraboo

5 out of 5 average rating, 84 reviews

Perfect Location, Downtown Baraboo w/ Hot Tub

Aerial view of a house nestled among dense green trees, showcasing a red roof that contrasts with the surrounding foliage. The property is partially visible, with a patio area indicated by an outdoor table and chairs situated near the home.

Home in Portage

4.98 out of 5 average rating, 56 reviews

*NEW OWNR SPECL Private Getaway w/ Sauna + Hot Tub

Home in Baraboo

5 out of 5 average rating, 31 reviews

Secluded Cabin! Game & Escape Room! Baraboo/Dells

Family- and pet-friendly home rentals

A charming cottage is set on a grassy lawn, bordered by trees. A spacious deck extends from the house, furnished with tables and chairs, while steps lead down to the yard. A bird feeder hangs nearby, inviting local wildlife.

Home in Poynette

4.91 out of 5 average rating, 198 reviews

Island View Hideaway-Peaceful, On Water, Sandbars!

A single-story house is set on a well-maintained lawn, featuring a wooden exterior with a front porch and red railing. A paved driveway leads up to the house, while trees and open space are visible in the background under a clear blue sky.

Home in Baraboo

4.89 out of 5 average rating, 112 reviews

Wild Rose Ranch Guest house

Top guest favorite

A cozy seating area is highlighted by a green chair beside a small table. A white brick feature wall, designed for a wood burner, stands prominently, while large windows invite natural light and offer views of the lush outdoors.

Home in Portage

4.97 out of 5 average rating, 31 reviews

Chic Country Home w/ Sprawling Acreage

A charming cottage is nestled among tall trees, illuminated by soft outdoor lighting. The house features a welcoming front window, and a pathway leads to a fenced area. The night sky provides a serene backdrop to this inviting setting.

Cottage in Merrimac

4.81 out of 5 average rating, 26 reviews

Cottage next to Ski/Golf/Hike

Cabin in Wisconsin Dells

4.85 out of 5 average rating, 128 reviews

Wisconsin Dells Cabin in the Woods

A spacious outdoor dining area is set up on the wooden rooftop deck, featuring a rectangular table surrounded by woven chairs. Each place is elegantly arranged with red mugs and coordinating plates, while warm sunlight casts elongated shadows across the deck.

Condo in Wisconsin Dells

4.9 out of 5 average rating, 125 reviews

Downtown Dells Bachelorette/Bachelor Headquarters

Top guest favorite

A deck area is furnished with four Adirondack chairs, positioned around a fire pit. The backdrop features vibrant autumn foliage and a view of Lake Wisconsin. The space offers a peaceful outdoor retreat, inviting relaxation and enjoyment of nature.

Cottage in Poynette

4.92 out of 5 average rating, 60 reviews

North Cliff Cabin on Lake Wisconsin

Top guest favorite

The exterior of a spacious, multi-story house is displayed, featuring a wrap-around porch and large windows that allow natural light to enter. The side of the house is framed by greenery, and trees provide shade, enhancing the inviting setting.

Home in Wisconsin Dells

4.96 out of 5 average rating, 134 reviews

LeGros Chateau Guest Favorite!Downtown Dells

Family-friendly home rentals with a pool

The outdoor water park features multiple waterslides and a spacious pool area. Sun loungers and umbrellas are arranged around the pool, alongside playful water attractions. The lodge-style buildings are visible in the background, enhancing the resort atmosphere under a blue sky with scattered clouds.

Condo in Baraboo

4.91 out of 5 average rating, 11 reviews

Wyndham Glacier Canyon |1BR/1BA King Suite w/ Balc

The exterior of the resort is showcased, featuring a blend of rustic and modern architecture. Lush grass and well-maintained landscaping surround the entrance. A clear blue sky and subtle clouds highlight the inviting atmosphere of the complex.

Condo in Wisconsin Dells

5 out of 5 average rating, 17 reviews

3 bedroom deluxe Wyndham Glacier Canyon WI Dells

A cozy living room features two sofas, a lounge chair, and a stone-surrounded gas fireplace. Natural light filters in through a nearby window, creating a warm ambiance. Open shelving displays decorative items, and the kitchen area is visible in the background with modern appliances.

Villa in Wisconsin Dells

4.83 out of 5 average rating, 35 reviews

Ground level Poolside Villa on Lake Delton

Condo in Wisconsin Dells

4.83 out of 5 average rating, 247 reviews

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown

Home in Wisconsin Dells

4.89 out of 5 average rating, 224 reviews

Spacious Pine Cabin at Island Pointe

Condo in Wisconsin Dells

4.85 out of 5 average rating, 162 reviews

Mel’s Marina, on the River, walk downtown.

Apartment in Wisconsin Dells

Sundara Cottages-WI Dells-2Bd Suite

A tranquil water body reflects the serene facade of the resort building, framed by lush greenery. The clear blue sky overhead complements the vibrant natural setting, suggesting a peaceful environment for relaxation.

Condo in Baraboo

Three Bedroom Condo, Glacier Canyon, (A698)

Destinations to explore