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, 202 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

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, 197 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.

4.94 out of 5 average rating, 217 reviews

A cozy living room is featured with a soft beige sofa and an armchair in navy blue. A light rug with earthy tones is placed under a white coffee table, which holds magazines. A fireplace is surrounded by decorative mirrors, enhancing the welcoming environment.

Cottage in Stevensville

Cheerful Stevensville cottage, GREAT LOCATION!

Right in the prettiest area of Stevensville, Glenlord Cottage is an ideal location for your Southwest Michigan stay. Down the road you will find Glenlord Beach Park, a beautiful Lake Michigan overlook. Around the corner, an award-winning bakery. In Stevensville with its variety of restaurants, beaches, and shops, Glenlord Cottage is also within easy reach of many SW Michigan attractions and is well placed for visits to wineries, golf courses, and downtown St. Joseph with its shops and festivals.

Superhost

A cozy living area features exposed brick walls and large windows allowing natural light to fill the room. A dark sectional sofa contrasts with a patterned armchair, while a coffee table displays a decorative flower and various items. Warm hardwood floors enhance the inviting atmosphere.

Loft in Benton Harbor

4.92 out of 5 average rating, 212 reviews

Romantic Gastro Loft Retreat for Two

Located above the area’s hottest new restaurant, this newly renovated 1BR/1BA urban loft features classic finishes - exposed brick, high ceilings, maple floors, and quartz countertops. Cozy, comfortable quarters directly above the Houndstooth restaurant provide a fantastic opportunity to get a “taste” of the Benton Harbor Arts District. Muffled sounds of music and activity from the restaurant below are often present in the loft during evening hours. Some guests may find this objectionable.

4.97 out of 5 average rating, 142 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.

4.92 out of 5 average rating, 368 reviews

An open living area features exposed brick walls, large windows allowing natural light, and a cozy gray sofa facing a low wooden coffee table. A decorative globe and a tall plant add character, while shiny hardwood floors enhance the space.

Loft in Benton Harbor

The Candy Loft in Arts District - 1BR/1.5BA Luxury

Welcome to The Candy Loft in Benton Harbor's Arts District! This 1BR/1.5BA condo boasts exposed brick, a king bed, and an oversized river rock shower in a spa-like bathroom illuminated by a skylight. The chef’s kitchen features a luxe Kitchenaid gas range, and an air mattress adds extra sleeping space. Housed in a historic candy factory, with an office in a former elevator shaft, it’s walking distance to restaurants, a brewery, and a coffee shop. Note: on the 2nd floor, stairs required.

4.97 out of 5 average rating, 179 reviews

A spacious screened-in porch is adorned with comfortable seating and decorative pillows. Large windows allow natural light to fill the area, while a decorative table at the center holds a selection of refreshments. The serene view of the surrounding landscape enhances the inviting ambiance.

Cottage in Harbert

Hot tub open year round in modern/rustic cottage!

Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

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.

4.82 out of 5 average rating, 119 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.

4.87 out of 5 average rating, 210 reviews

Cottage in Benton Harbor

Hot tub! Red Tin Cottage of Harbor Country!

Welcome to The Red Tin Cottage of Harbor Country! Nestled in a quiet, rural setting Red Tin is a character-filled, country-chic escape in beautiful Southwest Michigan. Within minutes of award winning beaches, golf courses, wineries, breweries, and restaurants you can be close to it all and retreat back to peace. Take a dip in the hot tub on a starry night, relax in the claw foot tub after a day of play, or enjoy stories around the firepit with family and friends. Come gather!

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.

Apartment in Saint Joseph

A spacious living area is featured, showcasing a modern dark sectional sofa and a unique round chair. A glass coffee table sits at the center, complemented by decorative wall art and mirrors. Natural light fills the room through large windows with blinds.

4.91 out of 5 average rating, 220 reviews

*Luxury condo on water in St Joseph, 2 queen beds*

Modern and beautiful condo on the river going into the mouth of Lake Michigan near Silver Beach. Immediately next door to Clementine’s restaurant and within walking distance to many shops, bars, downtown, and the beach. Right next to Pier 33 Marina and docks and water rentals. You can eat, drink, fish, shop, and enjoy the beautiful scenery all at one spot. Silver beach/the pier is literally a short walk away!

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, 236 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

4.97 out of 5 average rating, 121 reviews

Home in Three Oaks

Great Yard, HOT TUB, Steps from Downtown

4.99 out of 5 average rating, 153 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

5 out of 5 average rating, 281 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

Best Couples Vacation, Private, Hot Tub, Creek,

4.82 out of 5 average rating, 206 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

5 out of 5 average rating, 162 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

4.92 out of 5 average rating, 173 reviews

A spacious living area is highlighted by large windows framing views of surrounding greenery. A cozy seating arrangement features a light-colored sectional sofa, paired with unique accent chairs. A modern coffee table made of wood and glass sits atop a patterned rug, with a sleek television positioned nearby.

Home in Union Pier

cozy new buffalo cabin, hot tub, 14m walk to beach

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 141 reviews

An outdoor relaxation area features a hot tub and a smokeless firepit, surrounded by comfortable seating. String lights hang above, illuminating the space. A small set of steps leads into the hot tub, with a towel draped casually over the railing. The grassy area provides a serene backdrop.

Home in Three Oaks

Pet friendly stylish retreat with sauna, hot tub

4.99 out of 5 average rating, 194 reviews

Barn in Stevensville

The Blue Barn - A cozy country getaway!

4.95 out of 5 average rating, 237 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, 332 reviews

Red Barn Lodge

4.88 out of 5 average rating, 210 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'

4.87 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

Guest house in Sodus Township

A spacious outdoor view is presented from a deck, overlooking expansive green fields and wooden fencing. In the distance, a large barn is visible, along with a few horses grazing nearby. A tree branch frames the scene, creating a peaceful country atmosphere.

4.81 out of 5 average rating, 340 reviews

Farm Cottage

5 out of 5 average rating, 146 reviews

A bright living area features a comfortable gray sofa adorned with decorative pillows, paired with a light brown armchair. Large windows provide views of lush greenery, while a striped rug anchors the space. A coffee table with a bowl sits at the center, enhancing the cozy atmosphere.

Home in Sawyer

The treehouse at Warren Dunes

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, 186 reviews

Experience Nature-Charming Cottage

4.98 out of 5 average rating, 115 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

5 out of 5 average rating, 92 reviews

The exterior of a two-story home is visible, featuring a welcoming front entrance. A large tree provides shade, with a swing hanging from one of its sturdy branches. Ferns line the landscape, creating a natural border around the property, complemented by a well-maintained lawn.

Home in Saint Joseph

4 Bedroom home w/pool in St. Joseph

4.97 out of 5 average rating, 235 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

Townhouse in Saint Joseph

A comfortable living area features a light gray sectional sofa adorned with pink and white accent pillows. A round coffee table rests on a patterned blue area rug, while a large television sits on a decorative media console. Windows allow natural light to illuminate the space.

5 out of 5 average rating, 18 reviews

Family Tides at Harbor Shores

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!