Family-friendly vacation rentals in Oconomowoc

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Top-rated family-friendly rentals in Oconomowoc

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

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Top guest favorite

Guesthouse in Richfield

4.94 out of 5 average rating, 254 reviews

Peaceful weekend or extended stay, full amenities

The Country Retreat at the historic Schmitz Family Farm is close to many attractions, ideal for couples, families, girls' weekends, extended stays, business travel, and is dog friendly. Enjoy a sunrise or sunset, get cozy at the fireplace, or indulge in the many activities our area has to offer. We feature two beautiful bedrooms, living room with two sleeper sofas (can also be used as a third bedroom, as door closes for privacy), laundry room, full kitchen, coffee nook, quiet deck and backyard.

Top guest favorite

Apartment in Kenosha

4.93 out of 5 average rating, 243 reviews

Cheerful Apartment in Downtown Arts District

Cheerful apartment in newly renovated building above Professional Acting Studio at edge of Kenosha's Downtown Arts District. Near Harbor, beach, 4 museums, art galleries, live entertainment, eclectic restaurants, diners, coffee shops, Trolly, bike paths, parks, lakeshore, antique stores and specialty shops, Prime Outlets, Bristol Renaissance Faire, Great America. Metra Line to Chicago, close to Milwaukee. My place is good for couples, solo adventurers, business travelers, friends and families.

Superhost

Apartment in Lower East Side

4.83 out of 5 average rating, 272 reviews

Best location in Milwaukee! Lower Duplex Unit

LONG TERM STAYS WELCOME. Unit is right off Brady Street, One of the best streets in Milwaukee. Over 70 places to eat or drink within walking distance, including bars with free shuttles to brewers games and Summerfest. There are many shops and grocery stores in the neighborhood and everything you could possibly want is a short Uber ride away. Best enjoyed by up to six people whether they be couples, friends, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Guest favorite

Home in Edgerton

4.92 out of 5 average rating, 119 reviews

Fun Lake Kosh Private Pier, Decks, Fire Pit, Grill

Gather at the White House: a stylish lake house with private pier, 4Br/2.5bath/beds for 15 people, fire pit, gas grill, huge yard, 2 wooded acres. Lake Koshkonong is one of WI’s largest, famous for its boat-up restaurants/bars, fishing, and water sports all accessible from our private pier. Located along 39/90hwy - 90 mins to Chicago/30 min to Madison. Perfect for entertaining: fully stocked, professionally cleaned, open floorplan, 3-story outdoor living, dining & patio, playroom & much more!

Guest favorite

Guesthouse in Elkhorn

4.98 out of 5 average rating, 166 reviews

Camp Wandawega: Lakeside 3 Bedroom Cabin

Overlooking the lake nestled right behind the main lodge, this cabin has 3 bedrooms, a half bathroom, a seating a room, a basic kitchenette & access to camp showers downstairs. One large bedroom has a queen bed, one room with bunkbeds, & one with a full bed to accommodate a max of 6 guests. (But the bunkbeds are best for kid-sized humans). Like all of Wandawega, it’s a back-to-basics, no-frills, primitive experience. Simple rooms, vintage furnishings. There is heat & a couple AC window units.

Superhost

Home in Kenosha

4.92 out of 5 average rating, 271 reviews

Where Family & Friends Gather to Create & Remember

Come gather, relax & celebrate at our 1 acre estate near beaches, dining & Carthage College! The designer interior features 5 BR/4 Bath, chef's kitchen with Viking & Subzero, Coffee/Espresso Bar, dining area for 12, 2 spacious family rooms with piano, fireplace and TVs. Enjoy dining, lounging & fun in the great outdoors w/hot tub, fire pit, basketball, pickleball, ping pong & lawn games! Beaches are walkable under a mile & near lively downtown w/ harbor, restaurants, shopping & museums.

Top guest favorite

Yurt in Cambridge

4.97 out of 5 average rating, 592 reviews

YurtCation

YurtCation is a relaxing getaway with lake frontage and nature trails. There is another yurt about 300ft up the same driveway. There are a total of two yurts and two homes that have access to the same 17 acre lake. Each yurt is off the grid and has their own queen-sized comfy bed, wood stove, Weber grill w/charcoal, fire pit, firewood, fresh water, canoe, and clean Porto Potty. Pet Policy: Max two - Must be in your sight and supervised at all times or $500 fine and check out immediately.

Top guest favorite

Home in Oostburg

4.96 out of 5 average rating, 187 reviews

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights, magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

Guest favorite

Cabin in Fort Atkinson

4.91 out of 5 average rating, 421 reviews

Cozy Lakeside Cabin on Lake Koshkonong

Cozy Lakeside cabin on Lake Koshkonong. Outdoor space for cookouts & lawn games, wrap around deck to enjoy lake views, dock access for swimming, walking distance to the lake's most popular restaurants and bar & grill. Close to Madison (45 min), Milwaukee(75 min) & Chicago(120 min), 1 bath/2 bedrooms featuring 1 Queen Bedroom , Full over Full Bunk with trundle & optional air mattress/sofa bed to accommodate guests.

Guest favorite

Home in Racine

4.94 out of 5 average rating, 156 reviews

Root River Home - Waterfront property - Sleeps 8+

Beautiful waterfront escape awaits you. Located along the Root River, Village of Caledonia, WI (Racine County) 10 Minutes / 3 Miles from North Beach (Lake Michigan) and only 5 minutes from Quarry Lake Park (Swimming and Recreation Area). Includes Kayaks, Canoes, Row Boat, Paddle boat, Firewood, Gas Grills, Netflix, WIFI, TV, and Wi and Playstation for the Kids, Ping Pong Table, outdoor firepits and much much more.

Guest favorite

Apartment in Fort Atkinson

4.95 out of 5 average rating, 249 reviews

‘The Part Time Local’ - A boho small town retreat.

A cozy, comfortable 1 bedroom apartment with eat in kitchen and separate living room. Newly remodeled bathroom with tiled shower. Mahogany floors and all the charm you'd expect in a 1907 Arts & Crafts. Stylish, boho décor to make anyone feel right at home. Private balcony with Rock River views. Laundry available. Downtown Fort Atkinson, walking distance to everything!

Superhost

Chalet in Williams Bay

4.88 out of 5 average rating, 249 reviews

The Bay Chalet

Featured in "At The Lake" Magazine in 2022! Enjoy the Northwoods of Lake Geneva! Just a 2-minute drive to Pier 290, Williams Bay public beach on Geneva Lake, lakefront park, boat launch and restaurants. 10 minutes to downtown Lake Geneva. 20 minutes to Alpine Valley. Enjoy Lake Geneva life while being tucked in the woods with a roaring fire in your cozy log cabin.