Family-friendly holiday rentals in Paw Paw Lake

5.0 out of 5 average rating, 17 reviews

Home in Watervliet

Stunning Home-Direct Waterfront access Prvt Dock!

This Beechwood Cove Cottage with a private dock is along Big Paw Paw Lake in spectacular Southwest Michigan! Enjoy your private lake access in a cove ideal for swimming, boating, or just soaking in the serene views. You are welcome to bring your own boat or rent one and dock it at the property's pier! *Amenities- Lily Pad raft, 3 Kayaks , 2 paddle boards, bags and more! *Enjoy Sunrise Coffee & Sunset Cocktails on the dock *Serene walks on Beechwood point Walk to Gazebo bar for Paw Paw Punch!

Indoor spacesKitchenLaundry

A charming cottage is surrounded by a lush green lawn, featuring white Adirondack chairs positioned around a fire pit. The cottage, with its blue exterior, has multiple windows that invite natural light. Trees dot the landscape, creating a serene, secluded environment.

4.95 out of 5 average rating, 101 reviews

Dog-Friendly Lake-View Cottage Near Wineries

Less than 2 hrs from Chicago & a short walk to Little Paw Paw Lake, enjoy the charming vibes of our quaint and completely private cottage. With a stunning view of the lake, indoor/outdoor fire areas, and a serene yard, our home is perfect for a weekend away, a Michigan staycation, or even as an overflow home when visiting family. Our cottage exudes old charm with its rustic hardwood floors and cabin-like porch, yet it has the right amount of modernity with high-speed WiFi and newer appliances.

KitchenFamilyWalkability

5.0 out of 5 average rating, 113 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 St. Joseph

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.

KitchenIndoor spacesParking

4.98 out of 5 average rating, 122 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.

FamilyIndoor spacesHospitality

A large, newly renovated home is set against a well-manicured lawn. The exterior features a combination of grey siding and a dark deck. A spacious balcony with white railing overlooks the yard, while large windows offer a glimpse of the interior. Trees provide additional greenery.

4.83 out of 5 average rating, 52 reviews

Paradise on Paw Paw Lake (add boathouse to fit 16)

Newly renovated home, directly on Paw Paw Lake! The first floor features 1 TV, 2 large bedrooms, a full bathroom, laundry room & fully equipped kitchen. Upstairs - 2 large bedrooms & another full bath and second living area with a trundle that sleeps 2. Enjoy the deck off that over looks Paw Paw Lake and large back yard with a firepit & grill! The home does come with a boat slip as well! (Please let us know prior to the stay if you'd like to use this) Pictures of Boathouse labeled as Sunroom

KitchenFamilyBackyard

4.99 out of 5 average rating, 191 reviews

A charming lake cottage is showcased, featuring a light-colored exterior and large windows that invite natural light. A welcoming front deck is visible, with steps leading down to a landscaped yard and the surrounding greenery, enhancing the serene outdoor environment.

Home in Benton Harbor

Panoramic Views/Beach/Hot Tub/Sauna/Cold Plunge

Welcome The Windover! • Private Beach • Panoramic Lake Michigan Views • Hot Tub, Sauna, Cold Plunge, Outdoor Shower •Expansive Yard /Outside Activities • 4 minutes to downtown St. Joseph, The Benton Harbor Arts District, and Harbor Shores • Centrally located Close to 6 Local Beaches Fine and Casual Dining World Class Golfing Wineries Breweries Nature Parks Mountain Bike Trail Park 1/4 from Property Curious Kids Museum Compass Fountain Silver Beach Carousel St. Joseph Lighthouse

Indoor spacesFamilyAccess

4.9 out of 5 average rating, 255 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.

FamilyKitchenBarbecue

4.97 out of 5 average rating, 145 reviews

A Home with a Forest Scent and the Sound of Waves

Escape to Pure Michigan! This charming home is a short walk to Hagar Beach and just a quick 10-minute drive to Silver Beach. Love golf? Tee off at Harbor Shores, Lake Michigan Hills, or Paw Paw Lake Golf Club. Sip and savor at Contessa Wine Cellars and Filkins Vineyards, or pick fresh fruit at Jollay Orchards and Fruit Acres Farm—all just a short 15-minute drive or less! After a day of adventure, relax by the cozy outdoor fireplace—the patio glows beautifully at night with string lights.

Indoor spacesKitchenWalkability

The exterior of a two-story home is depicted, featuring a paved driveway that leads to a welcoming front door. Lush green landscaping surrounds the house, with neatly arranged flower beds and trees enhancing the natural setting.

4.95 out of 5 average rating, 150 reviews

Great Paw Paw Lake Getaway - Close to Beaches!

Beautiful updated home is perfect for families with upstairs and downstairs sleeping space. Upstairs has a spacious master bedroom with 1 king bed and sofa bed and a master bath. Bedroom 2 boasts 2 twin size beds as well as bedroom 3 (2 twin beds). Downstairs has a spacious kitchen & living area with 2 futon beds. Outside a spacious patio with fire pit close by. Home is close to Jollay Orchards & Contessa Wine Cellars. Beautiful St. Joseph and Silver Beach are 20 minutes away.

KitchenFamilyDecor

Holiday home in Watervliet

A modern kitchen features white cabinetry and stainless steel appliances, including a large refrigerator and oven. An island with a dark countertop offers additional prep space and seating for two. Warm pendant lighting hangs above the island, while wood flooring adds a natural touch.

The Play Pen @ Paw Paw Lake

Welcome to The Play Pen @ Paw Paw Lake - your perfect Southwest Michigan getaway! This 4-bedroom retreat is conveniently located just a block from Paw Paw Lake public beach and ideal for families, friends, couples, golf trips, and wine weekends. Spend your days boating, swimming, and enjoying Paw Paw Lake, then come home to relax and unwind together. The Play Pen @ Paw Paw Lake is the perfect home base for making memories in Southwest Michigan.

KitchenFamilyWi-Fi

4.97 out of 5 average rating, 36 reviews

4.91 out of 5 average rating, 407 reviews

Cabin in Watervliet

Riverview Cabin

Riverview Cabin is a bright riverfront studio retreat on 150 shared acres, perfect for couples or small families. Sleeps up to 4 with a king bed, futon, full kitchen, Smart TV, Wi-Fi, and a jacuzzi tub with scenic views. Relax on the private deck, gather around the fire pit, or explore 2.3 miles of riverfrontage, wooded trails, fishing ponds, and wildlife. Dog-friendly and just minutes from Lake Michigan beaches, wineries, and local attractions.

Indoor spacesKitchenAccuracy

5.0 out of 5 average rating, 41 reviews

A view from the deck captures the expansive lake with a wooden dock extending into the water. Multiple boats are visible, anchored in the calm lake. The sky is partly cloudy, allowing natural light to illuminate the scene, while green grass borders the deck area.

Cottage in Watervliet

Modern Lakehouse | Dock | Firepit | Kayaks | BBQ

Newly renovated 3BR lakefront getaway on Paw Paw Lake! Includes a private dock, 2 kayaks, 2 paddle boards, floating water mat, smokeless fire pit, family games, and a deck with water views. Swim, paddle, sightsee or relax. Minutes to Lake Michigan beaches, shopping, wineries, golf courses, and local breweries. A perfect spot for summer escapes, fall weddings, or full family vacations - life’s better on the lake.

KitchenIndoor spacesCleanliness

Popular amenities for Paw Paw Lake family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5.0 out of 5 average rating, 146 reviews

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

FamilyKitchenBiking

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, 133 reviews

The Oasis Retreat

FamilyKitchenOutdoor spaces

4.98 out of 5 average rating, 107 reviews

The exterior of the lake house features a multi-level design with a spacious patio area, highlighted by a fire pit surrounded by stone borders. A hot tub sits nearby, and comfortable seating is arranged under a covered balcony. Lush greenery provides a serene backdrop.

Cottage in Benton Harbor

Cheerful Sister Lakes 4 BDR Lake Hse w/ Hot tub.

KitchenIndoor spacesView

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, 160 reviews

Black Bear Lodge-Hot Tub and Game Room

FamilyKitchenCheckout

4.88 out of 5 average rating, 224 reviews

Cottage in Benton Harbor

Hot tub! Red Tin Cottage of Harbor Country!

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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, 252 reviews

Driftwood Shores-SH is a great fall getaway!

FamilyKitchenNearby

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, 291 reviews

Family Friendly Private Beach Home with Hot Tub

KitchenFamilyLayout

4.98 out of 5 average rating, 126 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

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Family- and pet-friendly home rentals

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.

4.84 out of 5 average rating, 202 reviews

Experience Nature-Charming Cottage

FamilyKitchenWalkability

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

Indoor spacesFamilyCondition

5.0 out of 5 average rating, 216 reviews

Barn in Stevensville

The Blue Barn - A cozy country getaway!

Indoor spacesKitchenSleep quality

Guesthouse 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.

Farm Cottage

FamilyKitchenCondition

4.83 out of 5 average rating, 376 reviews

4.85 out of 5 average rating, 129 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 St. Joseph

Silver Beach 2bd -1 block to downtown State Street

FamilyKitchenCheck-in

4.86 out of 5 average rating, 108 reviews

Glennhouse Getaway

Indoor spacesKitchenBackyard

4.94 out of 5 average rating, 142 reviews

Home in New Buffalo

New buffalo Farmstead main home pool hot tub

KitchenIndoor spacesBarbecue

4.98 out of 5 average rating, 175 reviews

Home in Sawyer

Luxe Cabin Minutes to Lake Michigan

KitchenFamilyQuiet

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 123 reviews

Beach-Themed Game Room & Pool Near Lake Michigan

KitchenFamilyView

4.96 out of 5 average rating, 102 reviews

Home in Sawyer

Atomic Acres-POOL, Summer 2026 Awaits!

Indoor spacesFamilyParking

4.98 out of 5 average rating, 160 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!

FamilyKitchenGetting around

4.97 out of 5 average rating, 247 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

KitchenFamilyHospitality

4.98 out of 5 average rating, 121 reviews

Condo in South Haven

SunKissed Sanctuary + Pool + Hot Tub +CentralLofts

KitchenIndoor spacesAccuracy

An outdoor gathering area features a fire pit surrounded by seating, inviting conviviality. Nearby, a bubbling hot tub is framed by trees, providing a secluded retreat. Dining tables with chairs offer ample space for outdoor meals, and a foosball table awaits action in the game room.

4.86 out of 5 average rating, 79 reviews

Private Modern Oasis: Fire pit, Hot tub, Sleeps 12

Indoor spacesKitchenCheck-in

5.0 out of 5 average rating, 36 reviews

Private 24-Acres| Heated Pool | Hot Tub & Pond

KitchenIndoor spacesHiking