Family-friendly vacation rentals in Grand Marais

4.9 out of 5 average rating, 410 reviews

A dining area features a rustic wooden table surrounded by two dark wooden chairs. A small potted plant is centered on the table. Natural light enters through a window dressed with white curtains, while a light fixture hangs above. A patterned rug covers the floor.

Home in Grand Marais

"Loftville": Sweet Lake Sup Loft near Grand Marais

Wonderful location for enjoying all that Grand Marais has to offer, while being slightly removed to enjoy the tranquil shoreline. Relax and listen to the waves crash from this newly buillt, charming, clean, and comfortable loft. Perched along the scenic lakeside, Croftville Road, you can enjoy the quiet Lake Superior life while being a short bike ride (use our bikes) to "the coolest small town in America", Grand Marais. Beautiful winter scenery at greatly discounted rates: check our calendar!

4.9 out of 5 average rating, 198 reviews

The setting sun reflects off the water, creating a shimmering pathway of light. Clouds are gently illuminated in soft shades of orange and pink, while the horizon showcases distant land outlines. The foreground includes tall grass lining the edge of the water.

Home in Port Wing

Kinney Valley Farm

This rustic, but modernized farmhouse is on 110 acres of woods and apple orchards. Snow is great now! Cross country ski trails are " skier-groomed" on our property. Multiple areas for groomed skiing are within 30-45 minute drives. Located just 3 miles from the south shore of Lake Superior, and 30 minutes from the Apostle Island Sea Caves, spectacular now with winter ice sculptures, Kinney Valley Farm is a cozy place to stay, while exploring the pastoral winter beauty of Northern Wisconsin.

4.75 out of 5 average rating, 184 reviews

A wooden deck features a round table with an umbrella and four metal chairs. Nearby, a bright yellow chair and a bench in a muted color add a pop of color. The exterior of the home is composed of white siding, with a door leading inside.

Home in Ely

Adorable, tiny 2 bdrm cottage in downtown Ely

Experience the best Ely has to offer while staying in your own single family home. This 750 sq ft ‘smart’ home is located one block from downtown Ely's shopping and dining establishments, within walking distance of walking trails & swimming beaches, close to the new (still in progress) paved bike trail between Ely and Tower, and just a few miles from the nearest BWCAW entry point. The home is furnished with fine hotel-quality linens, many amenities including central air and ‘smart’ technology.

4.97 out of 5 average rating, 337 reviews

The cabin is nestled on a wooded point, surrounded by lush greenery and rocky shoreline. The clear waters of Lake Superior gently lap against the bedrock, creating a serene and tranquil setting. Outdoor seating areas and a picnic table are visible on the grassy area.

Home in Two Harbors

Classic Vintage Log Cabin on Lake Superior

Classic, Vintage Log Cabin on 2.5 acres right on Lake Superior - a cozy step back in time! 250 ft. of private bedrock shoreline. 3 Bedrooms: 2 Queen, 1 Dbl. Large updated 3/4 bath, kitchen, and indoor wood burning fireplace. Outdoor firepit, firewood and picnic table. WiFi, TV, and DVD. Close to everything Two Harbors and the North Shore provide! A Pack and Play, booster chair & high chair are available. The Nightly fee is for 2 adults. There's a $25 fee/night/each additional guest.

4.91 out of 5 average rating, 744 reviews

A bright children's playroom features a soft rug at the center, surrounded by colorful toys and playful decor. Shelves stocked with interactive games and a rocking horse provide an inviting space for activities. Two small chairs are positioned nearby for seating.

Chalet in Two Harbors

Lakeview chalet by Gooseberry Falls with sauna

Spacious and family friendly chalet with sauna, game room, theater, kids room and more! Wake up to gorgeous views of Superior from your master bedroom, make breakfast in your fully equipped kitchen or drive two minutes to the Rustic Inn cafe, home to the best pie we've ever had (the North Shore mixed berry). After a busy day of exploring sites, from Gooseberry State Park to Split Rock Lighthouse, all within 10-15 minutes of your home base, you can unwind with beers at Castle Danger Brewery.

4.99 out of 5 average rating, 226 reviews

A spacious interior is highlighted by natural wood paneling and abundant natural light. A staircase with carpeted steps leads to the upper level, while large windows offer views of the surrounding greenery. A cozy seating area is visible, enhancing the open layout.

Chalet in Lutsen

Honeymoon House on Superior Pebble Beach

Nestled in the woods on the shore of Lake Superior, this home provides everything the North Shore has to offer. The house features sweeping lake views from all three bedrooms, a creek and bridge, two private pebble beeches, kayaks, and beautiful trees. Located in Lutsen, Minnesota only 15 minutes from Grand Marais. The house has heated floors, North woods art from local artists, comfortable beds, and unique architectural features. Perfect escape for weekend away or special occasion.

4.81 out of 5 average rating, 277 reviews

A living area features a navy blue sofa paired with a rustic wooden coffee table. A television is mounted on the wall, and light streams in through a sliding glass door leading to a balcony. A dining area with a small table is also visible.

Condo in Bayfield

One Minute Walk to Lake Superior. Brookside #3

Amazing location! No cleaning fee! This Condo sleeps 4, King bed & Queen sofa sleeper. Full kitchen, balcony, AC, CableTV, WiFi, BBQ and fire pit wood povided. Restaurant, bar and pool in July-Sept.Bayfield is a 2.3 mile hike or bike on the Brownstone Trail. Brookside is 5 minutes from Mt Ashwabay, Big Top, Bayview beach and multiple hiking trails. Ride a ferry ride to Madeline or cruise the Apostles. Sail, fish, kayak, golf, ski. $40 pet fee per stay. 🙂 No smoking allowed.

4.9 out of 5 average rating, 107 reviews

A charming wooden cabin is nestled among lush trees, with a visible balcony facing the water. A small beach area extends beside the cabin, featuring a few chairs arranged near the shoreline. Rocky formations lead into the calm water, reflecting the surrounding greenery.

Home in Beaver Bay

Northwoods Luxury on Private Black Sand Beach

Beautiful waterfront all-season home with 260ft private lake shore! One of a kind sandy beach on Lake Superior, 3 bedrooms with dramatic lake views and everything you need to make your trip memorable. If you've experienced Minnesota's North Shore, you know the secret beauty that awaits. From hiking, skiing and the famous Gitchi-Gami Bike Trail, the only challenge is deciding what do first...that is, if you can peel yourself away from the private beach and your cup of coffee.

4.93 out of 5 average rating, 133 reviews

The private cabin features a rustic wooden exterior, surrounded by lush greenery. A welcoming porch with steps provides access, while large windows allow natural light to fill the interior. The building is raised above ground on sturdy supports.

Cabin in Ely

Lakeside, Family Friendly Cabin

Welcome to Ely, Minnesota and the Boundary Waters! Private cabin contains unlimited access to B.W.C.A.W. wilderness and sits less than 100 feet from beautiful Farm Lake on the White Iron chain of lakes. Perfect place for couples, families (with kids), and furry friends (pets). Rates include all applicable state and local taxes, lodging fees, etc. Rates do NOT include rentals, pet fees, docking fees, or other ancillary charges.

4.86 out of 5 average rating, 232 reviews

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

NEED ISLAND SERENITY? Instant Book 7 Pines La Pointe on Madeline Island today! Come see how this 2 bedroom/2 bath cabin 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, allow guests the feeling of going back in time.

4.98 out of 5 average rating, 113 reviews

The exterior of a spacious cabin is depicted under a twilight sky, showcasing warm lighting emanating from multiple windows. The structure features multiple balconies and a covered entrance, surrounded by trees and natural landscaping.

Cabin in Lutsen

Lutsen Northwoods Retreat

NEAR SKI, GOLF, WINERY, BIKING, HIKING, SNOWMOBILE TRAILS!!! Located in the heart of Lutsen Mountains and the North Shore, the Northwoods Retreat boasts all of the amenities you would expect from a luxury hotel. This is the perfect place to relax…and when you’re ready to venture out, our recently built Lutsen Northwoods Retreat is conveniently located near most anything you choose to do while visiting.