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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 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, 204 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 exterior view showcases a modern multi-story building, featuring balconies with railings and stone accents. Lush greenery and decorative rocks landscape the property, creating a welcoming atmosphere. A paved road leads to the entrance, providing access to the well-maintained surroundings.

Guest suite in Wisconsin Dells

4.84 out of 5 average rating, 389 reviews

★GLACIER CANYON RESORT WITH WATER-PARK AMENITIES★

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.

Two light-colored Adirondack chairs are positioned on a grassy area, offering a view of the lush surrounding landscape. Wildflowers and tall grasses are visible in the background, providing a natural setting. A cluster of trees stands nearby under a clear blue sky.

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.

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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

The family room features a cozy seating area with a queen sleeper sofa and a stylish coffee table. A large Smart Roku TV is mounted on the wall, and an electric fireplace adds a touch of comfort. Natural light enters through nearby windows.

Condo in Wisconsin Dells

4.78 out of 5 average rating, 54 reviews

Dells Suite Dreams - Lake Access with Boat Slip

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!

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

Top guest favorite

A serene night view of the Wisconsin River is captured from a patio. The calm water reflects lights from nearby buildings and trees along the shore. A boat is moored nearby, enhancing the tranquil riverside ambiance.

Condo in Wisconsin Dells

4.94 out of 5 average rating, 54 reviews

Upper Dells River Walk [1BR]

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

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

Family- and pet-friendly home rentals

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

The hot tub is positioned on a deck with two glasses of red wine placed on its edge. A sunset casts warm hues over the water, while the silhouette of trees frames the scene. The distant hills create a serene backdrop.

Home in Poynette

4.85 out of 5 average rating, 272 reviews

Quietwater-Peaceful, On Water, Nature, Sandbars!

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

A serene view of the resort is captured alongside a calm body of water, reflecting the building's smooth façade and surrounding trees. The clear blue sky adds to the tranquil setting, creating a peaceful ambiance for guests.

Apartment in Baraboo

Two Bedroom, Glacier Canyon, (Z548)

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

Top guest favorite

A serene waterfront scene captures a marina lined with boats, reflecting vibrant orange and pink hues from the sunset. Lush green trees surround the area, while soft lighting illuminates the water. Well-maintained shrubbery frames the foreground, enhancing the tranquil atmosphere.

Condo in Wisconsin Dells

5 out of 5 average rating, 6 reviews

NEW! Canoe Bay Riverwalk Retreat- Waterfront/Pool

Destinations to explore