Family-friendly holiday rentals in Superior

The exterior of the historic Tudor cottage features a landscaped yard with a variety of lush green plants and trees. The charming entryway is adorned with an arched doorway and decorative brick accents, complemented by a gentle slope leading to the front steps.

4.93 out of 5 average rating, 143 reviews

The Tudor Cottage - Historic 3 Bedroom Home

Step back in time and experience the unique charm of this historic 1929 Tudor Cottage. Lovingly maintained, this home blends century-old character with modern comforts for a memorable stay. Our home is centrally located, making it the perfect home base for exploring the area. You are just a short drive away from UWS, UMD, and the vibrant shops and restaurants of Canal Park. The location also provides easy access to the scenic North and South Shores of Lake Superior for unforgettable day trips.

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A two-story home is set on a well-manicured lawn, surrounded by trees. The exterior features a combination of wood and stone materials, with large windows offering views of the yard. A driveway leads to the attached garage, and a patio area is visible at the front.

4.91 out of 5 average rating, 169 reviews

Entire Family-Friendly Billings Park Home!

This spacious home is just minutes from everything the Duluth/Superior Twin Ports area has to offer! Features 3 bedrooms, large living spaces, play area for younger children with books, games, and puzzles. Full-sized kitchen and dining area with sliding door to deck. Plenty of off street parking in driveway. Quiet neighborhood, 5 min walk to beautiful Billings Park and St. Louis River. 10-15 min drive to Park Point Beach, Canal Park, Spirit Mountain and 100+ miles of biking/hiking trails & more!

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4.91 out of 5 average rating, 193 reviews

A small, rustic bunk house is showcased, featuring a bright yellow door that stands out against the multicolored metal siding. The structure sits on a wooden deck, with additional features visible in the background, including a greenhouse.

Farm stay in Wrenshall

AirB-n-BAWK! The NEST @ Locally Laid Egg Company

Bunk with the Birds -kinda. Sleep in sight of the chickens in this tiny, rustic bunk house. 1/3 of the structure is for the chickens, the other 2/3 is for you - separated by glass. It's a chicken aquarium / PEEP SHOW! The Coop has 3 twins and a full-sized mattress. It is BYO Bedding so come with sheets and/or sleeping bag and pillows. There is a solar charger to charge small devices and run the lamp and fan. The structure is seasonally heated with a Porta Potty near-by, bring a flashlight!

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4.93 out of 5 average rating, 441 reviews

A spacious living room features a large sectional sofa arranged around a low coffee table, offering a comfortable seating area. Natural light filters through the dark blinds on the windows. The rich wood floors enhance the warm ambiance, leading towards a hallway.

Apartment in Superior

Historic + Modern lll across bridge from Duluth

This beautifully restored historic building features a bright, open 3-bedroom apartment with 11-foot ceilings, a spacious living room, and a modern kitchen with generous white quartz countertops. Enjoy newly finished wood floors, cooling gel memory foam beds, in-unit laundry, high-speed WiFi, a 4K Smart TV with cable, a wine cooler, elevator access, and free off-street parking. A perfect blend of charm and modern comfort that can comfortably house 6 guests. License #TBES-BEJSS8

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4.98 out of 5 average rating, 164 reviews

The tiny house sits elevated among evergreen trees, featuring a wooden deck that extends outward. Large windows allow natural light to flood the interior, while a red front door adds a vibrant focal point to the contemporary exterior.

Farm stay in Wrenshall

AirB-n-BAWK! The PERCH @ Locally Laid Egg Company

A stay for the Farm Curious! Enjoy a contemporary /rustic tiny house for a glampin’ experience with acres of berries and 100s of chickens Space includes: - Kitchenette with microwave, frig and coffee maker. - Full-sized bed & futon (sleep 4) - Overflow bunkhouse for additional fee (sleeps 3) - Deck, outdoor seating, fire ring / BBQ - Private outhouse, fire ring and hammock - Access to outdoor rinsing station (think shower), Earn field cred by joining in for chores

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Superhost

An outdoor patio is highlighted, featuring a fire pit surrounded by four white Adirondack chairs. Lush green grass extends around the patio, while two houses are visible in the background, framed by trees. A cozy atmosphere is created for relaxation and gatherings.

4.88 out of 5 average rating, 388 reviews

*EV Friendly*Pets Welcome * Canal Park 5 mins

Road construction won’t be an issue when you book this listing-adjacent to the Bong Bridge. Cleanliness and accommodation is priority. Fire pit with patio and a variety of seating arrangements. Off street parking. Conveniently located next to Duluth, Municipal Forest, Dog Park and Millennium Trail Head. And just minutes from the parks, trails and beaches, Canal Park, Bayfront Park, Park Point Beach, WI Point Beach, Hawks Ridge, Munger Trail, Ely's Peak.

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4.82 out of 5 average rating, 217 reviews

A spacious living room is showcased with comfortable seating arrangements, including a dark sofa, a mustard-yellow chair, and a large ottoman. Natural light enters through multiple windows, while a flat-screen TV is positioned on a low table, accompanied by minimalistic artwork on the walls.

Apartment in Superior

Barker's Urban Oasis

Welcome to our charming 2-bedroom apartment nestled in the historic East End neighborhood of Superior, Wisconsin. With its prime location, this cozy retreat offers a perfect balance of comfort, convenience, and local charm for an unforgettable stay. Barker's Urban Oasis is the upstairs unit in a duplex. This house was built in the early 20th century, during the Industrial Revolution, which contributed to Superior's early growth and prosperity.

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An open living space features light-colored walls, a comfortable seating area with two armchairs, and a dark couch. A wooden coffee table sits on a patterned area rug. The dining area includes a round table with grey chairs, while a kitchen space is visible in the background.

4.87 out of 5 average rating, 133 reviews

The Itty-Bitty Inn

Discover The Itty-Bitty Inn, a stylish 1BR/1BA family friendly retreat in South Superior. Embrace cozy comfort and modern charm in our perfect little hideaway. Great for a relaxing getaway or exploring the beauty of the area. Duluth/Canal Park --- 18 minute drive Spirit Mountain ... 20 minute drive Nemadji Golf Course ... 2 minute drive Children's Park ... 1 minute walk Barkers Marina ... 12 minute drive

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An open living area features wooden flooring and natural light flowing in through large sliding doors. The kitchen is equipped with modern appliances and a central island, while a dining table with four chairs offers a cozy space for meals. A comfortable seating area is arranged for relaxation.

4.96 out of 5 average rating, 124 reviews

Beauty at Short-4 Bed 3 Bath Near Lake Superior

Spacious 4 Bedroom, 3 Bath Home, with Custom Bar, dart board, and oh so comfortable! Come Stay and relax in our Centrally located Superior WI, minutes to Lake Superior and Duluth, MN, beautiful home! Off Street Parking and Outside Deck, Grill, and Firepit. Totally remodeled Superior WI Home. Former Home of baseball Hall of Famer, Dave Bancroft. Lic # CHWR-CMZNJK

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A modern kitchen presents light green cabinetry paired with a large island featuring bar stools. Pendant lights hang above, and stainless steel appliances are visible. The open layout invites natural light, with a cozy seating area and a welcoming entrance to the left.

4.95 out of 5 average rating, 259 reviews

The Treasure House- Near Duluth & Pet Friendly!

Come enjoy a stay at a newly renovated home. A perfect fit for both couples & families! 5 minutes from Barkers Island & less than 15 minutes from Duluth & Canal Park. You will find this a welcoming, cozy & relaxing home. The home is Pet Friendly. BE SURE to include your pet(s) in your reservation since there is a $75 nonrefundable pet fee.

KitchenIndoor spacesHospitality

4.86 out of 5 average rating, 379 reviews

Apartment in Superior

Terry Flats #7

This unit is located on the 3rd floor of this 3-story building and is accessible only by stairs and there is no elevator. It has a spacious layout with a living room, bedroom, office, bath, and a kitchen that is open to the living room. Large windows throughout the unit, extra closet space, pantry, and a breakfast bar.

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