Family-friendly holiday rentals in South Haven

A spacious hot tub is illuminated by soft blue lights, inviting relaxation. String lights hang above, casting a warm glow over the surrounding backyard area, which is highlighted by a fire pit and black outdoor chairs. A hammock can be seen in the background, adding to the outdoor charm.

4.98 out of 5 average rating, 157 reviews

Private Hot tub | Mins. Lake Michigan & downtown

🔥 Year-round hot tub ⛸️ Close to outdoor ice skating rink 🌟 Dreamy backyard space 🛍 1/2 mile to downtown South Haven ☕️ Keurig Duo w/ complimentary coffee pods 😍 Picturesque front porch ✨ Clean & cozy home 🏖️1 mile to Lake MI beaches 🍷 Near The Lakeshore Wine Trail 🍺 Several breweries nearby 🌞 Beach necessitates included 🚲 Several bikes included 🤩 Top rated home in South Haven 🧑‍🍳 Fully stocked kitchen ⚡️ High speed internet 📺 2 smart TV’s 🧺 Washer & dryer 👶 Portable crib & high

A spacious outdoor deck features a screened sunroom with a wooden rail. Several chairs and a table are arranged for dining. Green grass surrounds the deck, while trees provide natural shade. The structure is attached to a two-story home, creating an inviting outdoor space.

4.91 out of 5 average rating, 137 reviews

Charming, spacious sunroom, a/c, close to beach/dt

Barefoot Cottage is a beautiful, sparkling clean home with central a/c. We are walking distance to downtown South Haven. Pack up the beach wagon and toys for a short 1.7 mile drive to South Haven’s beautiful north and south beaches. This beautiful home sleeps up to 8 guests, features a fully equipped kitchen, and spacious fenced in backyard. Enjoy the large outdoor deck with a spacious sunroom that provides a relaxing place to grill, play games, read or just enjoy time with family and friends.

4.8 out of 5 average rating, 274 reviews

A cozy space features a daybed with plush pillows and warm throws. Soft lighting is provided by pendant and string lights, while earthy wallpaper enhances the room's charm. A comfortable chair and a textured rug add to the welcoming ambiance.

Tiny home in Coloma

-Shingle Diggins Cottage-

Enjoy whimsical luxury in quaint cottage. Steeped in the History of charming Coloma once called Shingle Diggins in the early 1800's for the wooden shingles manufactured in the area. Cozy comfort with everything you need. Nestled in the heart of the stunning Great Lakes Region, Southwest Michigan Wine Trail, and the Fruit Belt. Full kitchen, 100% linen sheets, fully enclosed private backyard for fur babies, easy access to lakes, beaches, dining, wineries, breweries, outdoor adventures, and more.

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 out of 5 average rating, 231 reviews

Driftwood Shores-Enjoy a Winter Getaway!

Spring is coming! We are an excellent base for the Holland Tulip Festival and are open from May 1 - 8. Enjoy a trip to beautiful South Haven along the shores of Lake Michigan. Driftwood Shores is a charming 1,680 sq. ft. home in the Harbor Club Resort. It has everything you need to enjoy a peaceful family vacation, friends getaway, or girls weekend out. The Resorts Indoor/Outdoor Pool with retractable roof and outdoor hot tub is open year around from 7 AM to 10 PM. It is included with your stay.

4.99 out of 5 average rating, 100 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.

4.94 out of 5 average rating, 159 reviews

An inviting outdoor space features a large deck with colorful chairs, a picnic table, and a grill. Surrounding greenery adds a natural touch, while a curved walkway leads to a bicycle rack. The area is designed for relaxation and enjoying time outdoors.

Cottage in South Haven

BLueVieWToo/STePS to The BeaCH/LaKE VieWS/Downtown

TOES IN THE SAND/STEPS TO THE BEACH/WATER VIEWS FROM THE DECK! Attractive 2 bedroom cottage (500 Sq. Ft.) located adjacent to Packard Park with it's sandy beach. Bring your flipflops and head to the water! Living space, 2 beds/1 full bath/a beautiful kitchen w/ Washer/Dryer. Large deck to sit and relax and watch the sunset. Wifi, TV, Beach chairs, umbrellas, toys, towels, BIKES included Come be at home with us! Not just a rental, this is a home! **ADJACENT 4 BED HOUSE ALSO AVAILABLE**

An enclosed indoor pool area features a large, clear swimming pool surrounded by spacious tile flooring. Illuminated by natural light from the ceiling, several lounge chairs are positioned at the poolside, providing a relaxing atmosphere for guests.

4.97 out of 5 average rating, 106 reviews

The Northern Anchor: Your Perfect Getaway!

The new enclosed subdivision pool & hot tub are now open! Enjoy our beautiful vacation house. Fully furnished with loads of thoughtful details. Perfect for families with kids or for groups/individuals looking for a relaxing get away. Close to everything: beaches, downtown shopping, wonderful restaurants, award winning golf courses, pick your own orchards, beautiful wineries and much more. Visit us year round - from snowy woods to sandy beaches - the Northern Anchor has something for everyone.

4.97 out of 5 average rating, 158 reviews

A charming ice cream shop features a bright blue exterior with scalloped details, inviting customers with an open sign. A menu board stands at the entrance, showcasing an array of ice cream options. The door, framed in white, adds to the welcoming atmosphere of the storefront.

Flat in South Haven

Captain's Loft in the heart of South Haven

Located in the heart of downtown South Haven! We are steps from Lake Michigan, South Beach, the Black River, Restaurants & Shopping. Recently updated with new sofa, queen bed & fresh beach vibe! An upstairs unit, its 25 steps to a perfect getaway that is close to everything that downtown South Haven has to offer! Private access to a rooftop deck with showstopper views of the river & marina. 1-bedroom with a private entrance from the sidewalk, a small kitchen, bathroom, and living room.

A dining area features a wooden table set with delicate dishware. Soft, muted colors dominate the space, with a decorative shelf and hanging mugs adding charm. A small clock and various decorative elements complement the warm atmosphere, while natural light filters through a nearby window.

4.83 out of 5 average rating, 185 reviews

Rustic Glamhouse

Explore the beach, farmers market and wine tastings! Enjoy this charming upstairs apartment that encompasses a mix of chic rustic, modern decor and the atmosphere of home. You’ll have the entire place all to yourself. 1.1 miles from the heart of South Haven and South Beach on Lake Michigan, this is a perfect place if you are looking for beach time and a place to relax. This apartment is a 2 bedroom, 1 bath and can sleep up to 6 people. There is 1 king, 1 full, 1 twin, a daybed and a couch.

The spacious living area features modern lighting fixtures hanging above a dining table. Soft seating includes a couch adorned with decorative pillows. Windows allow natural light to illuminate the room, while artwork is displayed on the walls, contributing to a cozy and functional atmosphere.

4.96 out of 5 average rating, 269 reviews

Six On The Beach

Brilliantly decorated, very clean accommodations and centrally located in the heart of South Haven's sugar sand beaches, dining, and shopping. This exceptional condo features a fully stocked kitchen with stemware, plates and cooking utensils. Washer and dryer included. This location has it all, within a matter of steps, there are unique boutiques along the shopping district, numerous Restaurants and South Beach, everything this lakeside community has to offer is right there.

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.

4.98 out of 5 average rating, 248 reviews

Family Friendly Private Beach Home with Hot Tub

5 min walk to Private Beach 10 min drive to Downtown South Haven 18 min drive to Downtown Saugatuck Escape to our 3BR South Haven home in an exclusive community, just a 5-min walk to a private Lake Michigan beach. Comfortably sleeps 8. Features a private hot tub, chef's kitchen, and cozy fireplace. Perfect for families, you're just a short drive from downtown South Haven & Saugatuck. Your luxurious lakeside retreat awaits! Experience South Haven With Us & Learn More Below!

A comfortable living area features a beige sectional sofa with plush cushions, paired with a round wooden table. A large shelving unit displays various toys and books, while natural light enters through three windows framed by light curtains.

4.98 out of 5 average rating, 100 reviews

SunKissed Sanctuary + Pool + Hot Tub +CentralLofts

A stylish, historic lower-level loft featuring exposed brick and ductwork paired with true floor-to-ceiling walls for much-needed privacy. Designed by a family for families, this South Haven retreat blends charm, comfort, and convenience in a walkable location close to South Haven's countless activities. Amenities at Central Lofts include year-round access to a pool and hot tub, a fitness room, and seasonal access to a spacious shared patio with three grills.

Popular amenities for South Haven family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.81 out of 5 average rating, 119 reviews

A spacious living room is filled with natural light from a large window. A comfortable gray sofa, red armchair, and black accent chair are arranged around a glass coffee table. A fireplace is set against an attractive wall, and a television is mounted above it.

Flat in Bridgman

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

4.85 out of 5 average rating, 473 reviews

A charming red cottage is nestled among vibrant autumn foliage. A screened-in porch with blooming flowers adds character, while a set of steps leads to a welcoming hot tub area. The exterior is complemented by neatly landscaped greenery and a gravel path.

Cottage in Saugatuck

The Oriole

A charming two-story house features a covered front porch with white rocking chairs. Neatly trimmed shrubs and freshly mulched flower beds enhance the welcoming exterior. An American flag is displayed, and a well-maintained lawn adds to the overall appeal of the property.

4.93 out of 5 average rating, 118 reviews

Family Vacation Home two Blocks from Lake Michigan

Tiny home in Michigan City

The exterior of a red tiny house is framed by greenery, showcasing a wooden deck with railing. A hot tub is positioned on the deck, while a door and windows illuminate the structure, providing a welcoming atmosphere in a private yard.

4.99 out of 5 average rating, 223 reviews

The Studio at the Dunes

4.86 out of 5 average rating, 198 reviews

An outdoor area is shown featuring a hot tub positioned on a wooden deck. The red exterior of the cottage contrasts with the surrounding green grass and wooden fencing. A glass door leads into the main structure, enhancing the inviting rural charm.

Cottage in Benton Harbor

Hot tub! Red Tin Cottage of Harbor Country!

Guest suite in Saint Joseph

A well-appointed kitchen and dining area are presented, featuring white cabinetry and essential appliances. A wooden dining table with six chairs invites gatherings, while ample natural light brightens the space through a nearby window. The warm-toned flooring complements the overall inviting ambiance.

4.86 out of 5 average rating, 242 reviews

Charming 2BR St Joseph Retreat Peaceful Setting

4.96 out of 5 average rating, 138 reviews

Black Bear Lodge-Hot Tub and Game Room

A spacious living and dining area features large windows that overlook Lake Michigan, allowing natural light to fill the room. A comfortable sectional couch and a wooden dining table with chairs provide ample seating. Unique light fixtures enhance the modern design.

4.91 out of 5 average rating, 221 reviews

Endless Lake Michigan. Cozy & Spacious w/hot tub!

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 264 reviews

A welcoming porch is shown, featuring a comfortable seating area under a wooden canopy. Lush greenery surrounds the entrance, with a fenced yard visible in the background. The home's exterior is accented with pale siding and a front door marked with the house number.

Home in Saugatuck

Fenced inyard! Walk downtown. Hot Tub! Winter deal

Guest house 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, 650 reviews

Rainbows End 🌈 Plensa

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, 185 reviews

Experience Nature-Charming Cottage

4.97 out of 5 average rating, 206 reviews

The exterior of a cozy tiny home is showcased, featuring a light-colored facade with blue accents. A small front porch includes a welcoming door and seating areas. A lush green lawn surrounds the home, with trees providing shade in the background.

Home in Holland

🌷The Tiny Tulip🌷 Family & Pet Friendly

4.84 out of 5 average rating, 164 reviews

A modern kitchen is presented, featuring dark green cabinetry and a chic hexagonal backsplash. Stainless steel appliances include a microwave and an oven. A light fixture hangs above, illuminating the space, which also includes a wooden countertop and a small dining area with a table.

Flat in Saugatuck

Walk downtown! Winter & spring deals. Cute& bright

4.89 out of 5 average rating, 350 reviews

A charming red cottage is surrounded by lush greenery, with a welcoming front porch and light-colored door. Bright windows frame either side of the entrance, allowing natural light to illuminate the interior. A neatly maintained path leads through the garden to the cottage entrance.

Home in Saugatuck

Maple Ridge Cottage

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.

4.8 out of 5 average rating, 305 reviews

Farm Cottage

A charming vintage house is framed by two pink flowering trees. The house features a symmetrical façade with multiple windows and dark blue shutters. A small set of steps leads to the front door, enhancing the inviting appearance of the property.

4.68 out of 5 average rating, 156 reviews

SoHa House: 5 min to beach, shopping, restaurants!

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 146 reviews

A private pool area is framed by a white fence, featuring a clear blue pool surrounded by lounge chairs. Lush greenery and a large tree provide shade, while the serene view of Lake Chapin and distant trees is visible in the background.

Home in Berrien Springs

Lake House Retreat on the water

An indoor swimming pool is framed by large windows allowing natural light to fill the space. Comfortable chairs are positioned around the pool area. A shallow section with stairs is visible, alongside a section designated for lounging. The ambiance is relaxed and welcoming.

4.95 out of 5 average rating, 22 reviews

Lake Effect Loft +Beach+Downtown+Pool+Hot tub

4.95 out of 5 average rating, 287 reviews

The exterior of a blue and white two-story guest house is featured, showcasing large windows and a covered outdoor bar area. A paved patio area can be seen in the foreground, bordered by landscaping with rocks and plants, with a black fence enclosing the outdoor space.

Guest house in Zeeland

Honey Bee Ridge Guest House

4.96 out of 5 average rating, 73 reviews

Flat in South Haven

Downtown Loft: Indoor Pool, Hot Tub, Gym, Theater

Guest house in Cassopolis

4.97 out of 5 average rating, 179 reviews

Cozy cottage for two with hot tub!

4.97 out of 5 average rating, 238 reviews

A spacious living area features a brown leather sofa adorned with colorful pillows. A wooden coffee table is placed in front. A mounted television is positioned above a cozy gas fireplace, complemented by blue walls and natural light filtering through white shutters. A small dining area is visible in the background.

Apartment in Douglas

Cozy condo with fireplace perfect for fall fun.

An indoor heated pool is surrounded by sleek tile flooring and ceiling-mounted ventilation. A colorful mural depicting a sunset over water enhances the space. Pink inflatable flamingos float on the water, alongside blue inner tubes. Comfortable lounge chairs with striped cushions are arranged nearby.

4.98 out of 5 average rating, 59 reviews

Nautical Retreat – Indoor Pool, Sauna, HotTub MORE