Family-friendly holiday rentals in St. Joseph

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.

4.85 out of 5 average rating, 128 reviews

Silver Beach 2bd -1 block to downtown State Street

The historic McNeil House is located on State Street just one block from Downtown restaurants, shops, and the Bluff. You won't find a better or more convenient location when visiting this beautiful city! We're offering smaller groups an opportunity to stay in our historic home by renting the main floor that sleeps up to five guests. The upstairs will not be rented during your stay, so you'll have the house to yourself but won't have access to the upstairs. Only available during the off season.

FamilyIndoor spacesBeach

4.93 out of 5 average rating, 230 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.

KitchenFamilyWalkability

Guesthouse 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, 207 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.

Indoor spacesFamilyOutdoor spaces

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.

5.0 out of 5 average rating, 107 reviews

4 Bedroom home w/pool in St. Joseph

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

FamilyIndoor spacesTV

4.98 out of 5 average rating, 118 reviews

Cabin in Coloma

Cozy Cabin in the Woods

Just under two hours from Chicago and only 1/2 mile from Hagar Beach, this beautifully updated 100-year-old cabin offers a peaceful retreat in the woods. Surrounded by tranquil landscapes and towering trees, you’ll enjoy the perfect blend of rustic charm and modern comfort. Tucked along a quiet dirt road, the cabin is ideally located 15 minutes from South Haven and 10 minutes from St. Joseph making it close enough for dining, shopping, and activities, yet far enough to unwind in nature’s calm.

Indoor spacesFamilyQuiet

4.92 out of 5 average rating, 117 reviews

Cabin in Stevensville

Randi's Blue Cabin in Grand Mere

Take it easy at this unique and tranquil getaway. This 500 square foot cabin is conveniently located off 1-94 Exit 22, it seems like a world away from the hustle and bustle, yet close to everything. Built in the 1930's or 1940's I have kept the wonderful original woodwork, but updated the cottage with a new bathroom and a complete kitchen. Steps away from the Michigan State Park of Grande Mere known for its miles of trails through the woods, dunes, inland lakes, and access to Lake Michigan.

KitchenFamilyCheck-in

Superhost

Cottage in Stevensville

4.89 out of 5 average rating, 160 reviews

Escape to The Sunshine Cottage of Harbor Country!

Cozy up at The Sunshine Cottage of Harbor Country. Surrounded by award-winning beaches, state parks, wineries, and breweries this location boasts endless activities within a short walk, bike, and drive. With a large backyard and extended porch deck, the cottage offers outdoor fun and entertaining all summer long, or retreat for a cozy winter getaway. The cottage is in close proximity to Lake Michigan and Grand Mere State park - sand dunes, hiking trails, and nature adventures all seasons.

KitchenFamilyView

4.92 out of 5 average rating, 150 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.

KitchenFamilyView

4.96 out of 5 average rating, 115 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.

FamilyKitchenComfort

5.0 out of 5 average rating, 210 reviews

Barn in Stevensville

The Blue Barn - A cozy country getaway!

Welcome to “Blue Barn” vacation home, a country retreat located between beautiful St. Joseph beaches and several Baroda wineries. A welcoming, open floor plan makes it easy for your group to spend time together. Enjoy the crisp white bedding, fully stocked coffee and wine bar, and private fire pit to unwind with friends and family. Grand Mere State Park, Weko Beach, and several local breweries are all just a short drive from this ideally located property.

Indoor spacesFamilyValue

4.92 out of 5 average rating, 242 reviews

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.

Condo in St. Joseph

*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!

FamilyKitchenQuiet

Guesthouse in Stevensville

An inviting kitchen features wooden cabinetry and granite countertops. A black 'welcome' sign is placed on the countertop next to a vase of fresh flowers. Kitchen appliances, including a coffee maker, are neatly arranged, creating a functional and welcoming space.

4.99 out of 5 average rating, 266 reviews

The Shire

Nestled on five secluded, tree-lined acres, with a pond, waterfall, fire pit, tree swing, basketball court and walking trails, The Shire feels a million miles away from it all - but isn't! We are only minutes away from wineries, breweries, amazing beaches, restaurants and shopping. (Notre Dame is an easy 30 minute drive). Southwest Michigan is a beautiful place to live! We'd LOVE to share it with you.

FamilyIndoor spacesBathroom

Popular amenities for St. Joseph family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 219 reviews

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.

Home in Benton Harbor

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

FamilyKitchenHiking

4.94 out of 5 average rating, 108 reviews

Home in Stevensville

A-frame • Hot Tub • Fire Pit • Wineries • Beach

KitchenIndoor spacesNearby

4.9 out of 5 average rating, 252 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

FamilyKitchenLayout

4.99 out of 5 average rating, 175 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

KitchenFamilyLocation

Apartment in Stevensville

A garden pathway leads from the house to the beach, surrounded by lush trees and colorful blooms. A charcoal grill is visible on the patio, and gray steps ascend towards the entrance. The tranquil Lake Michigan is seen in the background through the foliage.

4.92 out of 5 average rating, 886 reviews

Quiet Grand Mere Coach House on Lake Michigan

KitchenIndoor spacesQuiet

4.96 out of 5 average rating, 100 reviews

Home in Sawyer

Atomic Acres-POOL, Summer 2026 Awaits!

FamilyKitchenView

An inviting hot tub is positioned outdoors, surrounded by lush greenery. A wooden privacy screen adds to the tranquility, while an outdoor shower with modern fixtures is nearby. The patio area is designed for relaxation, creating a soothing space for unwinding.

4.97 out of 5 average rating, 288 reviews

Family Friendly Private Beach Home with Hot Tub

Indoor spacesFamilyAmenities

4.97 out of 5 average rating, 245 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

Indoor spacesFamilyHiking

Family- and pet-friendly home rentals

Superhost

A sleek entertainment area is presented with a mounted flat-screen TV against a marbled feature wall. A wooden media console below holds decorative items and media storage. Greenery from a potted plant complements the modern aesthetic, contributing to a harmonious living space.

4.88 out of 5 average rating, 346 reviews

Cozy & Clean Entire Home in Saint Joseph

KitchenIndoor spacesAmenities

5.0 out of 5 average rating, 149 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

Indoor spacesKitchenHospitality

4.95 out of 5 average rating, 131 reviews

Home in Buchanan

-The District 5 Schoolhouse-

KitchenFamilyGetting around

4.87 out of 5 average rating, 134 reviews

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.

Home in Benton Harbor

2 mins from beach/monthly stays available

Indoor spacesFamilyWi-Fi

4.88 out of 5 average rating, 218 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'

KitchenFamilyGetting around

Guesthouse 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, 337 reviews

Red Barn Lodge

KitchenFamilyHiking

Guesthouse in New Buffalo

A cozy bedroom features a spacious bed adorned with layered textiles and decorative pillows. Large windows provide views of the outdoors, while natural light is enhanced by wooden ceiling beams. A small dining area with chairs and a table is positioned nearby.

4.96 out of 5 average rating, 696 reviews

Rainbows End 🌈 Plensa

Indoor spacesKitchenDecor

4.92 out of 5 average rating, 399 reviews

Cabin in Watervliet

Riverview Cabin

Indoor spacesFamilyHospitality

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 121 reviews

Beach-Themed Game Room & Pool Near Lake Michigan

Indoor spacesFamilyView

The exterior of a two-story gray and green house is showcased, featuring a stone-accented garage and white-trimmed windows. Lush shrubs line the entrance, and a gravel driveway leads to the garage, set against a backdrop of greenery and a clear blue sky.

5.0 out of 5 average rating, 249 reviews

Driftwood Shores-SH is a great fall getaway!

KitchenFamilyWalkability

A private, heated pool is surrounded by a spacious patio, furnished with multiple lounge chairs. The two-story home features a balcony overlooking the pool area, with lush greenery framing the serene outdoor setting.

4.97 out of 5 average rating, 155 reviews

Private Pool 5 Minutes From Lake Michigan

FamilyKitchenPool

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.

4.83 out of 5 average rating, 197 reviews

Experience Nature-Charming Cottage

KitchenFamilyLaundry

4.91 out of 5 average rating, 131 reviews

A blue cottage is surrounded by tall trees, featuring large windows that provide ample natural light. A spacious deck extends around the front, with steps leading to the entrance. A chimney is visible on the side, adding to the cottage's charm.

Cottage in Sawyer

The Cranny at Michaels Nook

FamilyKitchenCheckout

4.87 out of 5 average rating, 119 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!

Indoor spacesKitchenAir conditioning

4.97 out of 5 average rating, 134 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

Indoor spacesKitchenAmenities

A three-story cottage with a white exterior and large front porch, situated at the corner of Cavelier Avenue and River Run. The building features bold windows and a classic roofline, surrounded by manicured grass lawns and a well-kept sidewalk.