Family-friendly holiday rentals in Benton Harbor

Four wooden chairs are positioned on a deck overlooking Lake Michigan. The sun is rising in the sky, creating a shimmering reflection on the water's surface. Trees frame the scene, adding a touch of greenery to the picturesque view.

4.98 out of 5 average rating, 200 reviews

Lake Michigan Views | Mins. to St. Joe | Hot tub

🌊 Spectacular Lake Michigan views 🌅 Deck overlooking Lake Michigan 🔥 Year-round, private hot tub 🌞 Beach necessitates included 📍 Minutes to downtown St. Joe & Silver Beach 🏖️ 5 Lake Michigan beaches within 5 miles 🌳 Private, quiet setting with outdoor seating ✨ Magical fire pit space ⛳️ Near Harbor Shores Golf Course 🛏️ King bed ♾️ Infinity gaming table ⭐️ Top rated home in St. Joe ☕️ Complimentary coffee & tea- Keurig duo 🧑‍🍳 Fully stocked kitchen ⚡️ High speed internet 🧺 Washer

4.99 out of 5 average rating, 524 reviews

A charming, rustic cabin is nestled among vibrant autumn foliage, showcasing a wooden exterior and a sloped metal roof. The cabin is partially obscured by trees, with golden leaves creating a warm frame around the structure, signaling a serene woodland retreat.

Farm stay in La Porte

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Guest house in Benton Harbor

A charming green cottage is nestled among trees, surrounded by well-kept landscaping and flower pots. A red umbrella shades a picnic table nearby, creating a welcoming outdoor space. The gravel path leads to the cottage entrance, framed by large windows for natural light.

4.94 out of 5 average rating, 195 reviews

Cozy Green Cottage with Private Beach

Cozy cottage hidden away in a quiet neighborhood 1.5 blocks from Lake Michigan, featuring a screened back porch perfect for morning coffee. Near the Benton Harbor Arts District, downtown St Joe, this cottage is surrounded by local restaurants, breweries, wineries, golf courses and shops. The beach is a year round destination, each season has its own wonders. Note: no TV, and WiFi can be spotty due to hills. Expect 90+ tiered steps to the sandy beach below. AC upstairs, original claw footed tub.

4.97 out of 5 average rating, 139 reviews

A light-filled living area features a black leather sofa with decorative pillows and a wooden coffee table. Natural light enters through large sliding glass doors that open to a balcony, offering views of the outdoors. A circular woven pouf adds textural contrast to the floor.

Flat in Saint Joseph

Luxury Waterfront Condo

A gorgeous top-floor 1200 sq ft condo is located in downtown Saint Joseph with a view of the Saint Joseph River. The condo is beautifully decorated and furnished with comfortable beds and spa-quality linens and toiletries. Both bedrooms have black-out curtains and flat-screen smart TVs loaded with Netflix. The open concept kitchen is supplied with everything you need to prepare a meal. The building has an elevator and dedicated underground parking. The roof has Instaworthy views. Free WIFI.

4.9 out of 5 average rating, 238 reviews

A well-maintained single-story home is seen alongside a spacious driveway leading to a two-car garage. The home features a charming front porch and neatly landscaped yard, with green grass surrounding the property and trees lining the background.

Cottage in Benton Harbor

Cottage near Hagar Beach Pet friendly with Hot tub

•Brand New Nordic Hot Tub• •September 2023 • Gather with family or meet with friends, there's plenty of room to stay the weekend. The inside of the home has refinished hardwood flooring throughout from the 1930's. The entire home is newly renovated giving it a classic Lake Michigan vibe. Only a few hundred feet from Lake Michigan's shoreline and one mile to pet friendly Hagar Park, there's a playground for the kids and plenty of beach to lay around on and enjoy with family and pet's.

4.95 out of 5 average rating, 108 reviews

The A-frame cottage is nestled among tall trees, featuring a blend of stone and wood in its design. Large glass windows create a connection with nature, inviting natural light into the living spaces. A pathway leads toward the entrance, surrounded by lush greenery.

Cabin in Stevensville

Idyllic A-frame in Michigan’s Harbor Wine Country

Follow a wooded path to a secluded mid-century modern cottage constructed of stone and wood reclaimed wood from a historic St Joe's rollercoaster. Retro pink ceramic tiles line an open-plan main floor surrounded by sliding doors. You will be surrounded by the great outdoors while sitting cozy inside by our electric fireplace. Located about 10 minutes south of downtown St. Joe, our Idyllic A-frame is a perfect location for the escape to SW Michigan that you've been dreaming about.

4.91 out of 5 average rating, 138 reviews

The exterior of a modern tiny house is seen surrounded by trees. Soft lighting strings hang above a fire pit with four Adirondack chairs arranged around it. Smoke rises from a fire, creating a cozy outdoor space.

Tiny home in Sawyer

Modern Minimalist Tiny House | Firepit | Nature

Welcome to our modern minimalist tiny house located a half mile from Warren Dunes State Park beach and 1.5 miles from all that Sawyer Michigan area has to offer. Tiny is the second dwelling on this property and is technically a mobile tiny house. While we do have electricity and water, much like an RV the drains run to holding tanks. This means VERY LIMITED WATER USE for showers and toilet flushing. It features a fully stocked kitchen, bathroom, and a queen bed in the small loft.

4.94 out of 5 average rating, 124 reviews

Flat in Benton Harbor

Cozy apartment minutes from lake

Enjoy your stay in a cozy, yet spacious apartment. Full bath tub for warm baths during the chilly season and shower to wash sand off your feet from trips to the beach only 9 minutes away. You can relax on the couch & watch Netflix, enjoy a warm beverage with your guests around the table or lounge in your own Queen-sized bed. There are many options for casual & fine dining, shopping, walking trails, enjoying stunning sunsets at Lake Michigan & wine tours just minutes away.

Superhost

An open living area features hardwood floors and a spiral staircase leading to an upper loft. Comfortable seating is arranged around a coffee table, with a gray sofa and a chair visible. Large windows invite natural light, creating a bright and inviting space.

4.81 out of 5 average rating, 118 reviews

Harbor House near Lake Michigan

Welcome to Harbor House- Your ideal beach adventure awaits! 3 bedroom home close to many exquisite beaches, wine country, dune hikes, and Harbor Shores Pro PGA golf course. Just a few miles from downtown St. Joseph, MI! We have a large backyard and huge deck for outdoor entertaining. Can sleep 6 adults comfortably, and 1-2 kids on a futon. Please note there is only one bathroom currently. 2 paddleboards for rent- beach is 2 miles away. Small dogs by approval only, with fee.

A ranch-style house is presented, featuring a welcoming front porch with two chairs. Colorful flowerpots and vibrant blooms adorn the entrance, complemented by a neat lawn. The exterior showcases a blend of subtle hues, highlighting the inviting atmosphere of the home.

4.87 out of 5 average rating, 129 reviews

2 mins from beach/monthly stays available

1200 sq ft ranch style house w 2 bedrooms, 1 bath. Main bedroom has 1 queen size bed, 2nd bedroom has twin size bunk beds w twin size rollaway bed which enables a total of 5 guests. Appliances available for use are stackable washer/dryer, fridge, stove, over the range microwave, and dishwasher. Newer propane grill is available for use. *bunk bed will be difficult for older individuals due to lower bunk being low. Bunkbeds are really designed for smaller children.

4.93 out of 5 average rating, 115 reviews

A serene sunset is captured over a calm lake, with hues of orange and pink blending in the sky. Silhouetted trees frame the view, while a hanging chair is visible in the foreground, offering a cozy perspective of the tranquil scene.

Cottage in Benton Harbor

Lake Bluff cottage, Unforgettable view and sunsets

We have recently renovated and brought this charming cottage, located less than 10 mins to the heart of St. Joes, back to life! It is perched atop a beautiful bluff, high above the Lake Michigan shores- highlighting expansive views and stunning sunsets. Come stargaze with us (starting this spring) at our wonderful Lake Michigan Cottage. Bring your fur baby to enjoy the getaway! ($150 pet fee) 5 night minimum for Holiday weeks (Thanksgiving, Christmas, 4th of July)

A single-story house is presented with a gray exterior and white trim. A welcoming front porch features seating and flower arrangements. The surrounding property is characterized by a large grassy area and trees, creating a peaceful setting.

4.92 out of 5 average rating, 234 reviews

The QT

Cozy country retreat. Whether you are visiting to explore Lake Michigan beaches (15 minutes away), the Lake Michigan Shore Wine Trail, the Makers Trail, or if you are invited to a wedding at the Blue Dress Barn (5 minute walk) or Sundance Studios (1 mile) this is the place for you! Fall asleep under the stars (skylight) in our brand new king size bed and wake up to a cup of coffee in a cheerful kitchen.

Popular amenities for Benton Harbor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 152 reviews

A cabin exterior is presented, featuring a screened-in porch that offers comfortable seating. The structure, painted in a muted green tone, is surrounded by trees and foliage. A set of steps leads to the porch, creating easy access to the welcoming retreat.

Cabin in Union Pier

Walk 2 Lake/Shops | Hot Tub | King Bed | Fireplace

4.98 out of 5 average rating, 107 reviews

A charming wooden cabin is surrounded by lush greenery, featuring a sloped roof and multiple gables. A spacious front porch is visible, framed by neatly trimmed shrubs. Tall trees provide a natural backdrop, enhancing the peaceful and serene environment.

Cabin in South Haven

Modern Log Cabin With Hot Tub Near Lake Michigan

5 out of 5 average rating, 278 reviews

The exterior of a circular, dark-hued building is illuminated by warm string lights during twilight. A private hot tub and a fire pit with chairs are visible, while the surrounding natural landscape emphasizes the peaceful setting.

Farm stay in Vandalia

Lux, Couples Hideout, Creek, Private Hot Tub,

4.98 out of 5 average rating, 148 reviews

The exterior of a farmhouse is displayed, featuring a two-story structure with a red roof and white siding. A spacious deck with seating overlooks the manicured lawn, which is surrounded by trees. Bright red chairs are arranged on the ground, inviting relaxation.

Farm stay in Galien

FARM 10 acres, pond, Hot tub, king bed 30 min ND

5 out of 5 average rating, 159 reviews

A welcoming entrance features a bright yellow door against a mint green facade. Brick steps lead to a patio area, adorned with potted plants and a vintage cooler. The sun casts a warm glow over the peaceful lakeside view.

Home in La Porte

UncleLarrysLakePlace HotTubKayaksPingPong

4.97 out of 5 average rating, 131 reviews

An aerial view showcases the spacious outdoor area, featuring a blue tennis court adjacent to a rectangular pool surrounded by lounge chairs. Lush greenery and trees frame the property, while a well-maintained lawn offers additional recreational space.

Villa in Niles

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

4.98 out of 5 average rating, 104 reviews

An outdoor area features a hot tub with illuminated turquoise water, surrounded by a patio adorned with string lights. The modern house showcases large windows, providing ample natural light, and a dining area with a table and chairs set under a nearby umbrella.

Home in Stevensville

Family Fun House: Hot Tub*Ping Pong*Nintendo*Fire

4.98 out of 5 average rating, 103 reviews

Home in Sawyer

Hot Tub | Fire Pit | Foosball | Playground

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 235 reviews

The cabin's exterior is framed by colorful autumn foliage, with vibrant red leaves and dappled sunlight filtering through the surrounding trees. Stone steps lead to the entrance, enhancing the rustic charm of the well-maintained landscape.

Cabin in Michiana

Luxury Cabin Getaway •2 min to Beach• 1hr Chicago

Guest house in Stevensville

The exterior of the converted barn is shown, featuring a rustic red facade with multiple windows on the upper level. Lush green grass and large decorative plants frame the building, while a charcoal grill is positioned on a patio area, providing space for outdoor gatherings.

4.98 out of 5 average rating, 330 reviews

Red Barn Lodge

4.88 out of 5 average rating, 209 reviews

The exterior of the barn showcases a vibrant red facade adorned with greenery. Large overhanging vines and trees frame the entrance, creating a welcoming atmosphere. A paved area leads to the barn, with side windows visible on the left. This setting hints at a rustic charm.

Cottage in Sawyer

Northwind Llama retreat 'Loft Cottage'

4.81 out of 5 average rating, 205 reviews

An open kitchen and dining area is visible, featuring a dark wooden table with three matching stools. The kitchen is equipped with white appliances and blue cabinetry, illuminated by natural light from a nearby window. The flooring is a mix of dark wood and light tiles.

Cottage in Benton Harbor

Beach Bliss | Pet Friendly W/Hot Tub Near Lake MI

4.97 out of 5 average rating, 255 reviews

Home in Three Oaks

Casa Gitana - Boutique Style Stay in Three Oaks

4.87 out of 5 average rating, 193 reviews

The cottage features a welcoming facade with blue shutters and a vibrant red front door. A decorative flag is displayed on the porch railing, surrounded by neatly manicured greenery and blooming flowers, contributing to the inviting outdoor space.

Home in Stevensville

Cheerful 3BR 2BA Country Cottage Near Attractions

4.85 out of 5 average rating, 124 reviews

A welcoming porch is featured, showcasing a comfortable seating area with a navy blue cushion sofa and two matching chairs. Lush greenery surrounds the entrance, and natural light illuminates the space through large windows.

Home in Saint Joseph

Silver Beach 2bd -1 block to downtown State Street

Guest house in New Buffalo

A cozy living area features a mix of modern and rustic decor, highlighted by large glass doors that open to scenic views. Warm wooden paneling surrounds comfortable leather seating and a coffee table, while large windows invite natural light into the space.

4.99 out of 5 average rating, 412 reviews

Rainbows End 🌈 Bourgeois

Family-friendly home rentals with a pool

4.85 out of 5 average rating, 109 reviews

A large screened front porch is furnished with several wooden rocking chairs and a wicker seating area. Natural light filters through the screens, showcasing the surrounding greenery. A small table sits centrally, creating an inviting space for relaxation and conversation.

Cabin in Three Oaks

Cabin with POOL in family resort!

Superhost

A secluded in-ground pool is surrounded by lush greenery and landscaped gardens. Several lounge chairs are arranged near the pool, which reflects the sky above. Flowering plants and shrubs frame the scene, creating a peaceful outdoor retreat.

Home in South Haven

4.83 out of 5 average rating, 185 reviews

Experience Nature-Charming Cottage

4.98 out of 5 average rating, 114 reviews

The heated in-ground pool features a diving board and a slide, surrounded by a spacious deck with lounge chairs and a shaded patio area. The inviting turquoise water reflects the clear sky, creating a relaxing outdoor space for leisure and enjoyment.

Home in Milford

Summer of fun Pool, Hot Tub, Huge Game Room CLEAN

Guest house in Cassopolis

4.97 out of 5 average rating, 189 reviews

Cottage for two with pool & hot tub!

4.97 out of 5 average rating, 234 reviews

A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.

Cottage in Union Pier

Designer Cottage Relax Pool Beach & Spa—Windjammer

4.98 out of 5 average rating, 150 reviews

A private in-ground swimming pool is surrounded by lush green grass and tall trees, offering a serene outdoor setting. Sun loungers are positioned nearby, with an umbrella providing shade. A colorful inflatable unicorn floats on the water, inviting relaxation in the sunny atmosphere.

Home in Douglas

Rustic Mid Century Pool Oasis. Steps from town!

4.98 out of 5 average rating, 105 reviews

Apartment in South Haven

SunKissed Sanctuary + Pool + Hot Tub +CentralLofts