Family-friendly holiday rentals in South Haven

4.95 out of 5 average rating, 100 reviews

Fire Pit | Walk to Beach, Kids Park & Downtown

Welcome to Seasons of South Haven Rentals, a collection of family owned, operated and custom designed vacation homes where creating memorable experiences and spoiling our guests is what we love most! Escape to cozy Ashwood Cottage centrally located in beautiful South Haven within walking distance to stunning beachfront views of Lake Michigan (2 blocks), kids plash pad (5 blocks), Kids Corner playground (1 block) and downtown (6 blocks). This fully renovated home is perfect for a family vacatio

KitchenIndoor spacesHiking

An outdoor space features a hot tub illuminated with soft purple lights, surrounded by a wooden deck. Cozy green chairs encircle a fire pit, with string lights adding a warm ambiance. A wooden sauna is visible, enhancing the retreat-like atmosphere of the backyard.

4.96 out of 5 average rating, 102 reviews

Fun Haven: Hot tub, Sauna, Fire Pit, Game Room

Escape to your private oasis nestled in the City of South Haven. This spacious 2-unit, 1 home set up offers the perfect retreat for big families/groups, with 2 separate living areas & kitchens across 2 floors, providing ample space & privacy for all. Amenities: - 7 person Hot tub - 6 person Barrel Sauna - Fire Pit w/ endless wood - Game room w/ Pool Table, Foosball, Arcade, Nintendo Switch, 75'' TV - Indoor & Outdoor Games - Balcony & Sunroom - Washer/Dryer - Cent. Air - Pack n Play & Highchair

Indoor spacesFamilyValue

A bedroom features a spacious bed adorned with white linens and a navy throw blanket. Exposed brick walls add character, complemented by framed ocean-themed art. A mirrored dresser and a closet with hanging space provide ample storage. Natural light filters through a nearby window.

4.97 out of 5 average rating, 113 reviews

Walk everywhere: Bikes: Pool & hot tub: Beach gear

✨Upscale historic loft building 🚶WALK EVERYWHERE 🕑 2:00 PM CHECK-IN ⭐️Central Loft amenities⭐️ ♨️ Hot tub 🏊‍♂️ Indoor heated pool 🎬 2 movie theaters 💪 Workout room 🏖️ Beach necessities included 🌊 1/2 mile to Lake Michigan 🚲 4 beach cruiser bikes included 🛍️ A block from downtown SoHa 🍷 Near The Lakeshore Wine Trail 🍺 Close to several breweries 🧺 Washer & dryer in condo ☕️ Keurig & standard brewing coffee pot 🧑‍🍳 Fully stocked kitchen ⚡️ High speed inte

Indoor spacesFamilyValue

An inviting outdoor area is featured, showcasing a heated pool beside a vibrant garden filled with blooming flowers. Stylish lounge chairs are positioned near the pool, while a shaded bar area is adorned with ferns and colorful blossoms, creating a relaxing retreat.

4.93 out of 5 average rating, 130 reviews

The Oasis Retreat

The Oasis Retreat is a newly remodeled home with a private heated pool & hot tub, just 4 blocks from downtown South Haven & close to Lake Michigan beaches, marina, trails, restaurants, bars & shops. Perfect for families & groups, the private backyard has an outdoor bar, fire pit, gas grill, pizza oven, ping pong, outdoor shower & detached guest unit w/ seasonal bath/shower. Inside: kitchen, laundry, fast WiFi, Roku TVs, heat/AC, sleeper sofa & upstairs loft. Pool: May-Oct Hot tub: Year-round

FamilyIndoor spacesBiking

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.

4.98 out of 5 average rating, 184 reviews

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.

FamilyIndoor spacesQuiet

4.98 out of 5 average rating, 123 reviews

Beach-Themed Game Room & Pool Near Lake Michigan

The Northern Anchor: Year round community pool & hot tub! The ultimate family getaway! 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.

KitchenIndoor spacesBackyard

A newly constructed home is set in a serene wooded area, featuring a blue exterior with stone accents. The welcoming front porch is adorned with decorative bunting, and a spacious yard is surrounded by lush green grass and tall grasses, providing a peaceful outdoor setting.

4.95 out of 5 average rating, 164 reviews

Happy Z's Retreat~ Walk to the Beach

Beautiful newer construction home in a serene wooded area with a huge yard and firepit and cozy front porch to enjoy in all seasons! *NEARBY ACTIVITIES * -Bike the Kal-Haven Trail -Walk to 1st Street Beach - Walk the lakefront and river paths -Enjoy our quaint downtown to check out restaurants and tasting rooms -Rent a boat or go on one of many boat tours offered in town. -Wineries -Golf -Shopping! -Close to the highway for day trips to the nearby Saugatuck/Douglas/Holland area.

Indoor spacesKitchenNearby

4.98 out of 5 average rating, 139 reviews

Home in Benton Harbor

LakeMichigan•Beach•Hot Tub•Sauna•Amazing Views

Welcome to Spyglass! If you are looking for a perfect place for that a visit to Lake Michigan any time of year, then The Spyglass has you coved. Whether you’re there for couple's retreat, family vacation or girlfriend’s weekend this gorgeous Lake front property with private beach has it all. Being located not too far off the beaten path, only 5 minuets to downtown St. Joseph the Spyglass is a perfect landing zone for all the nearby activities Southwest Michigan has to offer.

FamilyIndoor spacesSkiing

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, 289 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!

KitchenIndoor spacesTV

5 out of 5 average rating, 145 reviews

Benchbike,hottub,playground,3blks to beach,firepit

3 bedroom, 2.5 bath home, 3 blocks from Lake Michigan, 2 blocks to Kids Corner playground, 10 min walk downtown. 6 person hot tub! Super fun bench bike! Outdoor firepit All deluxe memory foam mattresses. 2 kings, 2 fulls, 2 twins. Sleeps 8 adults comfortably, 10 sharing full beds. Enjoy bikes (including bike for 2, bench bikes), 2 kayaks, picnic supplies, books, toys, and games. Foosball Giant Kerplunkit game Board games Kid and pet friendly. Sledding, iceskating nearby

FamilyKitchenAccuracy

A rustic log home is framed by vibrant autumn trees, creating a warm and inviting exterior. A spacious deck surrounds the front, complemented by natural landscaping. The stone chimney rises prominently against the blue sky, adding to the home's charming character.

4.96 out of 5 average rating, 158 reviews

Black Bear Lodge-Hot Tub and Game Room

Welcome to this beautiful log home on four quiet, park-like acres. Spend your days exploring the charming town of South Haven, soaking up the sun at one of the many local beaches, visiting Lake Arvesta Farms and Sports Comlex or wine tast at the many wineries in the area. 👙Hot Tub 🛏 King Master Suite 🎲 Game room 🔥 Outdoor fire pit (fire wood provided) 🍽 Fully stocked kitchen ♨️ Indoor fireplace (available Nov 1-March 31) 🏖 15 minutes from Lake Michigan

Indoor spacesKitchenBathroom

4.98 out of 5 average rating, 123 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

Welcome to our serene South Haven cabin. An elevated retreat where modern design meets a calm, grounding sense of escape. Thoughtfully styled to help you unwind and recharge, the space offers a quiet, effortless luxury you’ll feel the moment you arrive. Secluded yet convenient, you’re just 5 minutes from downtown South Haven and 4 minutes from North Beach. Perfect for days of lakeshore adventure and evenings of relaxed indulgence.

KitchenIndoor spacesSleep quality

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

Superhost

A spacious living area is furnished with a green sofa and a warm orange armchair. Natural light fills the room through large windows, complemented by decorative plants and a textured rug. A flat-screen TV and a wood-burning stove create a cozy ambiance.

4.89 out of 5 average rating, 74 reviews

HGTV Featured Mid-Century Beach Retreat

Indoor spacesFamilyAccuracy

5 out of 5 average rating, 24 reviews

Downtown Loft: Firepit, Pool/Hot Tub, Theater, Gym

Indoor spacesFamilySleep quality

4.96 out of 5 average rating, 441 reviews

Home in Fennville

Relax & Unwind in a Nature Lover's Retreat!

FamilyIndoor spacesValue

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.

4.92 out of 5 average rating, 131 reviews

Family Vacation Home two Blocks from Lake Michigan

KitchenFamilyBackyard

4.99 out of 5 average rating, 112 reviews

Home in Fennville

Hot tub, dog friendly, firepit, grill, wineries!

Indoor spacesKitchenLaundry

4.99 out of 5 average rating, 176 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

4.98 out of 5 average rating, 159 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!

FamilyIndoor spacesCondition

4.97 out of 5 average rating, 145 reviews

A modern living area is featured, showcasing a comfortable sectional sofa with accent pillows and a low wooden coffee table. Natural light floods in through large sliding glass doors, revealing a view of the serene outdoor space. A fan is positioned above, enhancing airflow.

Home in Fennville

Modern Secluded Cabin, Private Hot Tub, Fire Pit

Indoor spacesKitchenDecor

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 106 reviews

Glennhouse Getaway

FamilyIndoor spacesBackyard

4.96 out of 5 average rating, 246 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

Indoor spacesKitchenParks

4.97 out of 5 average rating, 189 reviews

A bright and airy kitchen area features white cabinetry and ample counter space. Blue stools are positioned at the peninsula. Light wood ceiling adds warmth, while modern light fixtures illuminate the open space that leads to the living area with a couch and decorative rugs.

Cottage in Fennville

Freshly Renovated 1940s "Sunshine Park Cottage"

Indoor spacesKitchenHiking

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, 199 reviews

Experience Nature-Charming Cottage

FamilyKitchenOutdoor spaces

Farm stay in Benton Harbor

4.98 out of 5 average rating, 120 reviews

Barn Loft at Flying Diamond Ranch - Near Beaches!

KitchenFamilyWalkability

4.99 out of 5 average rating, 114 reviews

Home in Douglas

Douglas Hideaway | Modern home w/ Hot Tub & Patio

Indoor spacesKitchenHiking

4.91 out of 5 average rating, 180 reviews

A wooden pathway leads to a cozy cottage nestled among vibrant autumn foliage. The cottage features a welcoming front door and decorative elements, creating an inviting transition from nature to the home.

Cottage in Holland

Cottage 5 min. To Saugatuck W/ Sauna + wood stove

KitchenFamilyParks

Superhost

Cabin in Watervliet

4.92 out of 5 average rating, 403 reviews

Riverview Cabin

FamilyKitchenLaundry

Family-friendly home rentals with a pool

Steps lead down through lush greenery to a sandy beach beside Lake Michigan. The calm blue water stretches into the horizon, while the clear sky creates a bright and open atmosphere. The wooden steps provide easy access to the beach area.

4.95 out of 5 average rating, 37 reviews

North Shore Hideaway

KitchenFamilyDecor

5 out of 5 average rating, 25 reviews

The Back Perch -3 bedroom-3.5 bath-Indoor pool

FamilyIndoor spacesAmenities

4.96 out of 5 average rating, 100 reviews

Home in Sawyer

Atomic Acres-POOL, Summer 2026 Awaits!

KitchenIndoor spacesCheckout

5 out of 5 average rating, 26 reviews

A studio condo features a queen-size Murphy bed with a light-patterned blanket and a cozy futon nearby. A small dining area with a table is positioned adjacent to the fully equipped kitchenette. Soft blue walls and natural light create a relaxed ambiance.

Condo in South Haven

Private Beach/Pool on Lake MI Condo

KitchenFamilyCheckout

4.97 out of 5 average rating, 246 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

KitchenIndoor spacesAmenities

5 out of 5 average rating, 110 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

Indoor spacesKitchenPool

5 out of 5 average rating, 16 reviews

Home in Saugatuck

Christine's Cottage | Special Summer Weekday Price

KitchenIndoor spacesOutdoor spaces

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.