Family-friendly vacation rentals in Madeline Island

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Top-rated family-friendly rentals in Madeline Island

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

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Guest favorite

A rustic A-frame cabin is set amidst tall trees, featuring a stone pathway leading to a fire pit with stacked logs. Outdoor seating is visible, and a patio umbrella provides shade, enhancing the inviting outdoor space.

Cabin in Herbster

South Shore A-Frame | Steps from Lake Superior

A peaceful, feel good place. Renovated rustic modern A-frame on Lake Superior's scenic south shore. Surrounded by evergreen and birch trees in an idyllic woodland setting. Enjoy walks to the beach (1/4th mile down road), breathtaking sunsets and beach bonfires, kayaking the famous seacaves, biking, hiking to waterfalls, shopping for vintage treasures or just relaxing/stargazing in the beautiful private backyard. A perfect home base for exploring the Apostle islands, Bayfield and Madeline Island.

KitchenFamilyView

4.93 out of 5 average rating, 263 reviews

Top guest favorite

The cabin's striking exterior features large cedar beams and expansive windows, blending seamlessly into the natural surroundings. A screened-in patio offers a view of the woods and lake, while a gas grill is positioned nearby for outdoor dining.

Cabin in Herbster

Cedar Ridge | Hand-Crafted Cabin with Lake Views

This newly built cabin will take your breath away. You’ll find the perfect blend of Northwoods rustic charm and creature comforts in this 3 bdrm cabin nestled in the woods overlooking Lake Superior’s Bark Bay. You’ll fall in love with all the care & attention its owners have put into every detail. From the stunning cedar beams that provide the backdrop to the incredible lake views to the hand-crafted interior woodwork and the beautiful kitchen, you will see how unique and special this cabin is.

KitchenIndoor spacesBackyard

4.97 out of 5 average rating, 180 reviews

Guest favorite

A round table with a glass top is surrounded by four beige, woven chairs beneath a large umbrella. In the background, a vibrant garden features tall purple flowers and a green lawn, while a BBQ grill and fire pit are partially visible.

Camper/RV in La Pointe

Camp on Main Street

2017 28ft Jayco Camper. Located downtown La Pointe; walking distance to shops, cafes, restaurants, bars, ferry boat, museum, golf course, marina, boat rentals, swimming pool, playgrounds. 2 min walk to Joni's beach. Tucked in our beautiful back yard (private to renter, not used by owner) behind the house we live. So close to everything but yet in the quietest part of Main Street. Ideal for families or couples. Max occupancy 4-6. Every person above 4 (approved only by host) is $30.00 a night.

KitchenFamilyLong stay

4.85 out of 5 average rating, 232 reviews

Top guest favorite

The exterior of an artisan-crafted lake home is shown at twilight, featuring large windows that reflect the soft evening light. Surrounded by greenery and wildflowers, a stone pathway leads to the entrance, enhancing the natural setting.

Home in Herbster

Stunning Bark Point Home on Superior's South Shore

One of a kind, open/loft-concept (see pics: it really is open) artisan-crafted lake home on Superior's south shore: paddle in summer/ice hike in winter. Breathtaking sunsets. 300+ feet of private shoreline or short walk to public beach. Great kitchen. Up to 8 people and most dogs welcome - PET FEE: pets are an extra $25 (there is a place to leave this next to the house manual on the kitchen counter) Scenic huge patio with built-in fire pit (BYO firewood) We hope you love it as much as we do!

FamilyIndoor spacesParking

4.97 out of 5 average rating, 433 reviews

Top guest favorite

A spacious outdoor deck with a cozy lounge area featuring a modern propane fireplace surrounded by plush seating. The deck is lined with trees, providing a serene, private setting. String lights are seen above, adding ambiance to the inviting space for relaxation.

Cottage in Bayfield

Bayfield Fruit Loop Retreat - Main Cottage

Welcome to the Bayfield Fruitloop Retreat, featuring a beautiful "Main Cottage" nestled in 7 acres of woods in Bayfield, Wisconsin. The property allows you to savor a peaceful & quiet northwoods experience but still minutes from several attractions & historic downtown Bayfield. The property is conveniently located just 5 minutes' drive or 2.5 miles from the center of downtown Bayfield. Located right on country Hwy J, a starting point for a self-guided tour around the city of Bayfield where a

Indoor spacesKitchenHospitality

4.98 out of 5 average rating, 124 reviews

Top guest favorite

The cabin exterior features logs and a screened porch, offering shaded seating. A wooden deck wraps around, and steps lead up to the entrance. A propane grill is visible, and greenery surrounds the space, providing a secluded atmosphere.

Cabin in Bayfield

The Copper Squirrel of Little Sand Bay DogsWelcome

A mature forest and a beautiful pond are what you'll see when you arrive at this cozy, secluded, full log cabin. The cabin was recently completely renovated (Mar/April 2025)from log to log and is stocked with everything you'll need for your stay. It has all new appliances, furniture, fixtures, bathroom, cabinetry. 💚 It is the perfect homebase to relax after a long day of hiking Frog Bay, Houghton Falls, Lost Creek Falls, Meyers Beach, or shopping in nearby Bayfield, Washburn, or Cornucopia.

KitchenFamilyAmenities

4.98 out of 5 average rating, 373 reviews

Top guest favorite

Cottage in Bayfield

Superior Sanctuary: Refined Rustic in the Woods

Escape to the tranquil shores of Lake Superior in our charming retreat! Nestled within the serene Brickyard Creek Community, this modern haven offers a perfect blend of rustic elegance and contemporary comforts. Immerse yourself in nature's beauty, unwind on the spacious screened porch, and cozy up by the fireplace. Your peaceful escape awaits. • Screened Porch with Swing Chairs • Access to Beach and Hiking Trails • Smart TV & Streaming • Modern Kitchen • Boat Slip Rental Available

Indoor spacesFamilyOutdoor spaces

4.87 out of 5 average rating, 199 reviews

Top guest favorite

The open living area features large south-facing windows allowing natural light to fill the space. A comfortable gray sofa and a supportive chair are arranged on a patterned rug. A small table is set up for work or dining, complemented by greenery from nearby plants.

Apartment in Bayfield

Sunny + Spacious Rental in the Heart of Bayfield

1 bedroom + den with additional queen bed in the heart of Bayfield's historic district, just steps to downtown shops, restaurants, and beaches. Located in the lower level walkout of our duplex, this private + newly remodeled apartment boasts bright spaces, big windows, and comfy furniture for lounging. Take in glimpses of Lake Superior from the open concept living room/kitchen/dining area and enjoy your morning coffee from the covered veranda while enjoying the fresh Lake Superior breezes.

FamilyKitchenOutdoor spaces

5.0 out of 5 average rating, 104 reviews

Guest favorite

A rustic red yurt is surrounded by a forest of trees. A large wooden deck offers a welcoming entrance and is equipped with a sturdy railing. Natural ground covers and underbrush can be seen nearby, creating a serene and natural setting.

Yurt in Bayfield

Bayfield Rustic Yurt 2 (Terra Cotta)

Nestled in the middle of the Bayfield County Forest, this rustic, minimally maintained yurt has direct access to miles of non-motorized rec trails (CAMBA single track and Mt Ashwabay nordic ski and hiking trails). Enjoy panoramic views of Lake Superior including; Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton and Michigan) and the Upper Peninsula of Michigan. Come prepared to relax, unwind and explore the wonders of the north woods. Yurt access is 3/4 mile uphill.

Indoor spacesFamilyWifi

4.95 out of 5 average rating, 409 reviews

Superhost

A spacious cabin nestled among trees showcases large peaked windows and a welcoming deck. Sunlight filters through the leaves, illuminating the cabin's wooden exterior and the surrounding forest foliage.

Cabin in La Pointe

7 Pines La Pointe on Madeline Island

Looking for Island serenity? Instant Book 7 Pines La Pointe on Madeline Island today! Come see how this 2 bedroom/2 bath cabin, tucked in the woods close to beaches, town and the golf course, offers tranquility and peace in one of the more far away desired destinations in all of the country. Beautiful high peaked windows and glass doors, with a very large deck located in a forest of trees on the picturesque/historic Madeline Island, which can give guests a feeling of going back in time.

Indoor spacesFamilyDecor

4.84 out of 5 average rating, 271 reviews

Top guest favorite

Cottage in Cornucopia

Borealis Cottage by Siskiwit Bay

Borealis Cottage sits on a 2-acre, private, wooded lot in the sustainably designed Sawgrass Community of Cornucopia. Light-filled cottage with open floor plan includes a sleeping loft, screened porch, gas fireplace, and fully-equipped kitchen. A quick, quiet walk from the cottage takes you to a private wooded path with access to Cornucopia Beach on Siskiwit Bay. Explore the Apostle Islands National Lakeshore--our cottage is located 4 miles from Meyers Beach and 20 miles from Bayfield.

KitchenFamilyTV

4.99 out of 5 average rating, 166 reviews

Guest favorite

A private outdoor patio is presented with a glass dining table surrounded by four chairs. Colorful flower pots with blooming plants add vibrancy to the space, complemented by natural stone and greenery. Steps lead up to the entrance of the home.

Farm stay in La Pointe

Hippophile Farm Get-a-way Garden Apartment

The space is a newly renovated apartment on the lower level of our home which is located at our private horse farm on Madeline Island. It is light, bright, with a modern and clean look. It has all the things you need to relax and rejuvenate after spending a day exploring Madeline Island. Enjoy the beautiful woods surrounding the apartment or take a walk to our beautiful stables on the property. Bring your horses if you wish, or just come to enjoy the scenery.

FamilyIndoor spacesParks

4.91 out of 5 average rating, 176 reviews