Family-friendly vacation rentals in Three Oaks

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Three Oaks

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

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Top guest favorite

A screened three-season porch features a comfortable hammock and two chairs with cushions. A small table sits between the chairs, and natural light filters through the surrounding windows, allowing views of the greenery outside.

Place to stay in Michigan City

4.98 out of 5 average rating, 116 reviews

Tryon Farm "Bees Place" 100 acres of nature/trails

Charming 2 bed 2 bath, unique modern barn house. Relaxing screened three-season porch. In warm weather hammock is up and ready for you! Private courtyard with Gas Grill/Swing. Chilly weather come warm up next to the wood stove. Large overhead windows offer natural light & night sky views. Great views throughout. Leashed pet welcome. Tryon Farm community offers over 100 acres of wooded walking trails, a fishing pond & tree swing. One mile to Shady Creek Winery, close to beaches, and brewery’s.

Guest favorite

A dramatic scene is captured featuring a lighthouse on a pier, surrounded by dark storm clouds. Lightning strikes illuminate the sky, reflecting over the water's surface. The structure stands prominently, with its red top contrasting against the ominous backdrop.

Home in Michigan City

4.9 out of 5 average rating, 371 reviews

Best Deal In Michigan City 1.3 miles to Beach

Quiet for a well deserved nights rest. Plenty of space for 4-8 guests indoors and out. Short drive to the Washington Park beach & zoo Walking distance to south shore train for a quick ride into the heart of Chicago. Less than a mile from uptown arts center and district Short drive to The National Lakeshore, that has great beaches, hiking, and biking trails! Have a day in the sun, and come back to relax, in a quiet backyard patio area equipped with grill & night lighting... Must be 24 to book

Top guest favorite

A light-filled living area showcases a soft, neutral sofa adorned with decorative pillows. A glass coffee table sits in front, complemented by a patterned accent chair. Two lamps provide subtle illumination, while framed artwork decorates the walls.

Cottage in New Buffalo

4.96 out of 5 average rating, 183 reviews

Voted #1 Family Getaway In SW MI for 2019-2024

Welcome to our home away from home. Spacious, comfortable interior and large wooded lot. 8 blocks to the beach - 4 blocks to downtown shopping, restaurants, bars etc. We have thought of everything to make your stay enjoyable and carefree. Sleeps 10 -12 comfortably. Our large decks, brick patio and backyard, make our home a great place to come back to after spending the day at the beach, touring wineries & craft breweries, or taking in the beauty & fun activities southwest Michigan has to offer

Guest favorite

A spacious living area is visible, featuring a modern sofa facing a wall-mounted television. High ceilings with wooden beams enhance the airy feel. Light from large windows creates a bright atmosphere, while a wooden dining table with black chairs is seen in the foreground.

Cottage in Sawyer

4.9 out of 5 average rating, 239 reviews

Cozy, Private & Inviting Tulip Tree Beach Cottage

Beautiful renovated beach cottage on a quiet tree-lined street. Private comfortable home perfect for a winter weekend away! Enjoy the best of Pure Michigan, 2 mi from Sawyer & 0.5 mi to Warren Dunes State Park. Plenty of outdoor space to play, skylights to soak up the natural light and central to wineries, restaurants and the Dunes. Grab local farm fresh produce, s’mores for the firepit and a local natural wine to sip as you watch the sun set from the huge back deck and large backyard.

Top guest favorite

A cozy loft space features a blue sofa with decorative pillows, positioned near a window dressed with bamboo shades. A small basket is placed nearby, and a shelf holds an assortment of books and games, providing a welcoming area for relaxation.

Cottage in Union Pier

4.96 out of 5 average rating, 200 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, pool, hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today and create lasting memories!

Guest favorite

A spacious living area features a comfortable sofa adorned with yellow and gray pillows. A coffee table sits centrally, complemented by an area rug. Large windows with bamboo shades allow natural light, while hardwood floors contribute to the overall ambiance. A decorative black cabinet is visible in the corner.

Apartment in Michigan City

4.94 out of 5 average rating, 136 reviews

Charming apartment in Arts District

Walk to outlet mall, art galleries, parks, restaurants, and Lake Michigan beach. Walk or drive to casino. This is a 2nd-story apartment in Michigan City's historic homes. A full 1,400 sq ft of space! Fully appointed, clean and beautifully decorated. Newly renovated kitchen and bath. WIFI. Access to beautiful back yard patio and deck. Great proximity to attractions. Great for couples, solo adventurers, and families with children.

Top guest favorite

A cozy corner features a leather armchair beside a wooden table draped with a patterned cloth. A vibrant yellow dresser with multiple drawers stands against the wall, complemented by a framed painting above it. Natural light enters through a large window adorned with white curtains.

Cabin in Benton Harbor

4.99 out of 5 average rating, 267 reviews

Charming Cabin-Private Beach & Golf

Why the rave reviews? This cabin is a unique and charming 2 bedroom retreat that sits atop a hill and is surrounded by elegantly sculpted terrain of Harbor Shores golf course and walking trails. The private beach on Lake Michigan is steps away. It is located in a quiet neighborhood and is close to family fun activities in St. Joe/Benton Harbor, fantastic restaurants, wine tasting, art galleries and quaint shops.

Guest favorite

An open living area is viewed, featuring a blue couch and wooden beams along the ceiling. A doorway leads to a bathroom area with floral curtains, while a glimpse of the kitchen's green cabinets is visible in the background.

Tiny home in New Buffalo

4.96 out of 5 average rating, 560 reviews

SoulShine Inn • Pets Welcome•Fully fenced backyard

Near Warren Dunes, the Galien River, breweries, and wineries. Relax here with a fully fenced yard, fire pit and patio for grilling and privacy. Darling, pet and child friendly Tiny House . Two bedrooms on one level with a queen bed in each. An extra loft for an additional sleeping space for two. The ladder to the loft is steep(pictured)This tiny house sleeps 6. Nema 14-50 outlet for EV. Bring your cord/plug

Superhost

Home in Michigan City

4.92 out of 5 average rating, 106 reviews

Beautiful home with Beach views in Beachwalk

Enjoy the open concept family room/dining area, flat screen TV, fireplace, and a farmhouse table that seats 12. You can also enjoy the sunset from the top floor "birds nest" with views of the Chicago skyline. The lower level is perfect for kids to watch TV and play games and is equipped with bunks that sleep up to 7 people. A Staircase leads to a private walkway for access to Lake Michigan.

Guest favorite

The exterior of a private cottage is displayed, featuring a large wooden deck with seating. A screened-in porch is visible, offering protected outdoor space. Surrounding greenery and trees enhance the natural setting, while the roofline slopes gently towards the back.

Cottage in Three Oaks

4.91 out of 5 average rating, 112 reviews

Private, Sun-filled Union Pier Cottage

Sunny, private cottage set on a half-acre facing woodlands. Quick drive to everything - beaches, hiking, restaurants, wineries, breweries, etc. High-speed internet available and desk with two monitors. Please be advised: reservation requests from first-time AIRBNB renters will be declined. You must have rented through AIRBNB in the past and received a high rating.

Superhost

An open floor plan is displayed, featuring a dining area with a large table and chairs. A comfortable living space with a sectional sofa is illuminated by natural light from multiple windows. A ceiling fan is centered over the room, enhancing the airy ambiance.

Home in New Buffalo

4.86 out of 5 average rating, 170 reviews

The Bright Yellow Retreat

The Bright Yellow Retreat is a pleasant, short walk to Lake Michigan beach. Our sunny, vibrant home sleeps up to six guests. Our open floor plan with plenty of windows offer bright and airy surroundings. Relax in our sunroom. The large back yard is well equipped with grill, lawn furniture and picnic furniture. And, pets are welcome.

Guest favorite

An inviting entryway features a bright blue door and a bench with blue and white striped cushions. A small shelf holds items above the bench, while a rug enhances the warmth of the wood flooring. Sunlight filters through a window, illuminating the space.

Home in Michigan City

4.9 out of 5 average rating, 135 reviews

Airy and bright, Cottage Blue Welcomes You!

Nestled in the walkable Sheridan Beach area of Northern Indiana’s gorgeous and expansive lakeshore along Lake Michigan. Comfortably sleeps 12 - 14 with the perfect amount of space to get together and getaway to your own private spaces. Please note that parties are not allowed and you must be 25 years or older to rent our home.