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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

A quaint gray house features a dark front door framed by two windows with flower boxes. A stone path leads to the entrance, surrounded by lush green grass and shrubs. The home's simple design is complemented by a picturesque backdrop of leafy trees.

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 sunroom features large windows draped with sheer curtains, allowing natural light to fill the space. A hanging swing chair invites relaxation, while a plush sofa is accompanied by decorative cushions. A vibrant area rug anchors the seating area, enhancing the serene atmosphere.

Bungalow in Baraboo

4.91 out of 5 average rating, 174 reviews

Close to Wisconsin Dells freshly renovated home!

Beautiful bungalow located 15 minutes away from Lake Delton and all Wisconsin Dells attractions. And 4 minutes from gorgeous Devils Lake park. 15 minutes from all 3 different winter activities. Place has a beautiful sunroom, where you can enjoy a quiet neighborhood and read a book on the swing chair. House comes with a full kitchen, air fryer, coffee maker etc. Wi-Fi and electric fireplace. Fire pit with comfy chairs. We have variety of board games. House could accommodate up to 9 people.

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 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.

A charming cabin structure is illuminated at night, showcasing its mid-century architectural style. The building features large, glowing windows that highlight the warmth inside, surrounded by lush greenery and gently lit pathways leading to a peaceful outdoor setting.

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

A cozy nook features a large window adorned with a stained glass design, allowing natural light to fill the space. A plush armchair sits beside a simple blue table, while a window seat is decorated with soft cushions, inviting relaxation in a wooden interior.

Cabin in Baraboo

4.98 out of 5 average rating, 353 reviews

Private Baraboo Bluffs Cabin with Peacocks!

This is a beautiful getaway surrounded by nature. It’s on 180 acres with walking trails. The vibe is unbeatable. You will find your peace. Hike! Relax in nature! Way up in the Baraboo bluffs and right by some of Wisconsin's favorite attractions. Minutes away from Devil’s Lake, ski hills and great hiking. Relax by the fire surrounded by nature. Nature therapy! Forest, wildflowers, and peacocks right out your window. Dogs allowed with prior approval but no other pets

Top guest favorite

A scenic view showcases the modern home nestled among vibrant trees on a Christmas tree farm. Rolling hills are seen in the background, adorned with foliage in shades of red, orange, and green. Neatly arranged rows of Christmas trees line the foreground.

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.

Top guest favorite

A dining area features a light wood table surrounded by six chairs, positioned beneath a modern light fixture. Green walls offer a warm contrast to white accents. A decorative centerpiece holds plants, while large windows allow natural light to illuminate the space.

Home in Baraboo

4.9 out of 5 average rating, 122 reviews

Green Door Getaway

Take a moment. Make yourself a cup of coffee in the bright kitchen. Find a cozy corner to read a good book. Grab the yoga mat and get your workout in while you stay. Spread out at the desk and finish your project. Connect with family and friends in the spacious living and dining areas. Enjoy a hike at a nearby State Park. Take in the thrills in the Dells. Ski down Christmas Mountain, Devil's Head or Cascade. Maggie's Green Door Getaway is ready for you to enjoy!

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.

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

A sandy beach area stretches along the tranquil shore of Lake Delton. White lounge chairs are arranged in neat rows, facing the calm water. Gentle waves lap at the edge of the shore, bordered by lush greenery and a stone embankment.

Condo in Wisconsin Dells

4.89 out of 5 average rating, 108 reviews

Lakefront Condo - Private Beach | Boat Slip| Pool

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.

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

An outdoor seating area is presented with comfortable chairs placed around a fire pit, set on a circular gravel pad. The log cabin is seen in the background, flanked by trees and lush grass, under a colorful sunset sky.

Cabin in Baraboo

4.82 out of 5 average rating, 11 reviews

Secluded Cabin! Fire Pit! Game Room! HotTub! Dells

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, 81 reviews

Perfect Location, Downtown Baraboo w/ Hot Tub

Family- and pet-friendly home rentals

A hot tub is shown in the foreground, its water illuminated in soft light. Behind, a cottage is visible with large windows revealing a warm, inviting glow. The exterior is adorned with twinkling lights that enhance the cozy atmosphere of the setting.

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

4.84 out of 5 average rating, 25 reviews

Cottage next to Ski/Golf/Hike

A modern cabin is set amidst tall trees, with a gravel driveway leading to the entrance. The cabin features a red-trimmed roof and is surrounded by lush greenery, providing a peaceful and natural atmosphere.

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, 124 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

A spacious living area features wooden paneling and a ceiling fan. A large flat-screen television is positioned on a media console, while a decorative plant adds a touch of greenery. Large windows provide ample natural light and views of the outdoor space.

4.98 out of 5 average rating, 42 reviews

Oasis on 188 - Brand new remodel! Lake Life!

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

A warm and inviting living area features wood paneling and exposed beams. A spacious sofa, adorned with patterned throws, faces a large flat-screen TV. Natural light filters through sliding glass doors that lead to an outdoor space. A rustic stone fireplace adds a cozy touch.

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.

A sculptural water feature cascades gently over natural stones, leading to an inviting infinity pool. The resort's exterior is highlighted by stone architecture, with large windows allowing glimpses of the indoor amenities. Soft lighting enhances the tranquil ambiance of the evening setting.

Apartment in Wisconsin Dells

Sundara Cottages-WI Dells-2Bd Suite

The spacious living area combines a fully equipped kitchen with a dining space and comfortable seating. A stone fireplace adds warmth, while large windows allow natural light to fill the room. Pendant lights hang above the bar-height countertop, enhancing the modern design.

Condo in Sauk County

5 out of 5 average rating, 8 reviews

Wyn Glacier Canyon, 2 BR, 8 FREE WaterPark Passes!

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