Holiday rentals with a pool in Stevensville

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!

Nestled within a gated 67-acre resort and just minutes from the shores of Lake Michigan, this charming cabin offers a peaceful retreat ideal for couples, families, or solo travelers, blending rustic décor with modern comforts. Guests can spend their days exploring nearby nature trails, lounging by the pool, paddling across the lake, or unwinding on the porch. The perfect vacation for exploring nearby orchards and countryside, catching live music or theater, or just slowing down and recharging!

5 out of 5 average rating, 26 reviews

An aerial view captures the chalet community set along a serene shoreline, featuring a series of triangular-roofed buildings arranged nearby a clear blue waterway. Lush greenery surrounds the area, contributing to a tranquil lakeside atmosphere.

Cabin in Stevensville

101 is all the fun! Arcade + Pool + Beach

If this is your first time to the Chalet at the Lakes, it won’t be your last. This unique beach front gated community has it all! Chalet 101 - 2 bdrms and is located across from the pond. Not beachfront. The community includes heated pool, tennis courts, pickleball courts, private beach, 3 playgrounds, shuffleboard, basketball courts, sand volleyball, 2 community fire pits, and direct access to Lincoln Park Beach. And for adult vacays, you are just minutes from breweries and wineries galore!

4.97 out of 5 average rating, 105 reviews

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.

Apartment in South Haven

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

5 out of 5 average rating, 93 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

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.

4.99 out of 5 average rating, 219 reviews

Home in Vandalia

Quiet Couples' Retreat, Stock Tank Pool, Nature

Escape to you own private sanctuary in the heart of Michigan's beautiful countryside--surrounded by trees, birds, and wildlife. Leave the noise behind and reconnect in this romantic setting. Imagine sunning in our little stock tank pool, reading a book, or enjoying a cool drink. It is the perfect place for some serious soul care. Or visit the 45 minutes away touristy locations.....Amish Country Shipshewana, Lake Michigan, or Wine Country. Then, come back and enjoy the peace and quiet.

4.98 out of 5 average rating, 45 reviews

Home in Stevensville

Modern Lake House w/ Private Pool near New Buffalo

A quick 90-min drive from Chicago - This modern, minimalist, airy, newly constructed home nestled in private sand dunes steps away from Lake Michigan beaches, Grand Mere State Park, and all that SW Michigan has to offer! Relax in the hot tub after a day of hiking, touring wineries/breweries, fine dining, or enjoying the beach. Complete with its own private pool, fire pit & hot tub, ‘The Wedge' offers you a unique escape to connect with nature - a perfect getaway with friends & family!

4.96 out of 5 average rating, 194 reviews

The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.

Home in Michigan City

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Beautiful home in the heart of Beachwalk, across the street from Lake Kai, pools, basketball & tennis courts and 2 blocks to Lake Michigan. This home is bursting with charm. Front porch runs the width of the house. Dining area opens up to family room with a lovely fireplace. Stunning master bedroom w/walk-in closet and beautiful new bathroom with all the finishes. 3 more bedrooms upstairs, one with full bathroom attached and the other 2 sharing bathroom. 5th bedroom on the lower level.

4.92 out of 5 average rating, 26 reviews

An aerial view captures a cluster of chalets arranged around a spacious parking lot near the water's edge. The surrounding landscape features lush greenery and tranquil blue waters, with various outdoor amenities visible, including pools and recreational areas.

Home in Stevensville

Lake Michigan Beach Cottage + Pool + Games

Escape to our newly remodeled chalet that is steps away from Lake Michigan. With 6 beds, it's the perfect getaway for couples, families, or small groups. Enjoy access to a private and public beach, pools, sports courts, fishing ponds, and playgrounds. Located next to Lincoln Township Park and near Grand Mere State Park plus nearby breweries, wineries, and distilleries. Relax, explore, and create unforgettable memories at this cozy lakeside retreat. Your perfect vacations awaits!

4.92 out of 5 average rating, 26 reviews

A large outdoor pool is framed by lounge chairs and umbrellas, inviting relaxation under the sun. Adjacent, a bright living area features a blue couch, accent chairs, and a coffee table, with natural light streaming through multiple windows.

Home in Saint Joseph

New St Joseph Resort House with POOL

Come enjoy all that Southwest Michigan has to offer in our stylish house in the Harbor Village Resort development, within walking distance to St Joseph with boutique shops, kids museum/carousel/splash pad, and beaches! Relax in the stylish decor in this new 3 br house. Soak up the sun in the large pool right across the street! The Inn at Harbor Shores Resort is also at your doorstep with -Golf - Spa - Plank's restaurant/bar, - Conference center, c - Coffee shop - Marina

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

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today! Create lasting memories!

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

Waterfront property with a private hot tub, pool, and tennis court, making it an ideal destination for those seeking both relaxation and recreation. Visit beautiful Southwest Michigan and stay at the St. Joe Overlook. Take a swim in the pool, unwind in the hot tub, take the kayaks out for a river cruise, or sit by the fire. Enjoy this stunning location and top-notch amenities. A trip to the St Joe Overlook is the perfect place to gather & reconnect. Maximum Guest Count 16.

4.85 out of 5 average rating, 75 reviews

A clear view of the pool area is presented, showcasing a refreshing blue pool surrounded by a concrete patio. Lounge chairs and a dining set with an umbrella are positioned nearby, while a trampoline is visible in the background. The house features a deck with steps leading down to the pool.

Home in Saint Joseph

Updated 3 bdrm house w/ pool near beach & country

Your family will be close to everything when you stay at this centrally-located place. 10 minutes to wineries 10 minutes to Silver Beach 10 minutes to downtown St Joseph 5 minutes to Grand Mere State Park 45 minutes to Notre Dame 90 minutes to Chicago Our house is extremely comfortable for singles, couples, and families. Come relax and enjoy. We have everything you need for a perfect stay.

Popular amenities for Stevensville rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 3 reviews

Home in South Haven

Evergreen Acres • Woodland Preserve • Private Pool

4.93 out of 5 average rating, 114 reviews

The exterior of a multi-level house is depicted, featuring a combination of siding and stone accents. Large windows are present, along with balconies on the upper levels. A paved driveway leads to a garage, surrounded by greenery and a clear blue sky.

Home in Michigan City

Beautiful home in Beachwalk/Notre Dame weekends

4.83 out of 5 average rating, 186 reviews

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

Experience Nature-Charming Cottage

4.92 out of 5 average rating, 121 reviews

A modern dining area features a wooden table surrounded by sleek black chairs. Behind it, a vibrant mural of South Bend adds color to the space. A cozy living area with a large sectional sofa and ample natural light can be seen through the open layout.

Home in South Bend

Large, Cozy, Theatre, Pool, Walk to ND Restaurants

4.88 out of 5 average rating, 25 reviews

The exterior of a classic farmhouse is showcased, featuring a heated in-ground pool with clear blue water. A spacious deck is furnished with seating and an umbrella. The house has a two-story structure with multiple windows, allowing for natural light to brighten the surroundings.

Home in Sodus Township

Modern Farmhouse w/ Pool Near St Joe

4.67 out of 5 average rating, 3 reviews

A spacious brick home is set against a backdrop of manicured land, characterized by a large front lawn with neatly maintained grass. Vibrant trees, including a blossoming pink one, add a touch of color to the exterior. A clear blue sky completes the serene scene.

Home in Baroda

Holden Retreat

4.94 out of 5 average rating, 177 reviews

A private hot tub is set in a wooden enclosure, surrounded by a serene natural landscape. Steps lead up to the hot tub, offering easy access. Two white Adirondack chairs are positioned nearby, inviting relaxation in the peaceful outdoor setting.

Home in Union Pier

New Hot tub Heated Pool Union Pier

5 out of 5 average rating, 24 reviews

Home in Coloma

Luxury Estate with Heated Pool and Hot Tub

Condo rentals with a pool

Beach Vibes on Lake Michigan

5 out of 5 average rating, 27 reviews

South Haven North Shore condo

5 out of 5 average rating, 5 reviews

An outdoor pool is surrounded by lounge chairs, providing a relaxing area for guests. The three-story building features balconies on the upper floors. Clear blue skies add to the inviting atmosphere, enhancing the setting for relaxation and leisure.

Condo in New Buffalo

Perfect Location Condo Pools Walk to all Beach 1.5

4.97 out of 5 average rating, 39 reviews

A spacious deck is shown, featuring a wooden table with an umbrella and string lights illuminating the area. The view of the ocean is visible in the background, with a sunset casting soft colors in the sky. The side of the building is also visible, with multiple windows.

Condo in Coloma

Amazing Beach Condo with pool and great sunsets!

An indoor heated pool is enclosed by large glass windows that allow natural light to fill the space. Comfortable lounge chairs are arranged nearby, alongside a pool ladder leading into the clear blue water. The brick walls contribute to a modern and inviting ambiance.

5 out of 5 average rating, 12 reviews

Schoolhouse Suite: Indoor assoc. pool, hot tub!

4.94 out of 5 average rating, 95 reviews

A modern living room features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, while two lamps provide soft lighting. Artwork adorns the wall above, accompanied by a round mirror reflecting the space.

Condo in New Buffalo

Nightingale Dunes - Modern beach town retreat

4.94 out of 5 average rating, 93 reviews

A dining area features a wooden table surrounded by six chairs, creating a space for gathering. A spiral staircase leads to an upper level, while nautical-themed decor adorns the walls. An adjacent open doorway reveals additional kitchen space, enhancing the home's inviting layout.

Condo in New Buffalo

New Buffalo Getaway Condo

A bright living area features a spacious gray sofa and a light-colored coffee table on a patterned rug. Natural light streams through arched windows, illuminating a dining table with white chairs. A textured accent wall adds interest, adorned with decor elements reflecting the beach town setting.

5 out of 5 average rating, 11 reviews

1/2 Mi to Beach & Lake Michigan: Condo w/ Pool!

Other holiday rentals with a pool

4.96 out of 5 average rating, 82 reviews

The exterior of the cottage is presented, showcasing a spacious screened-in porch framed by greenery. The flat roofline and large windows invite natural light, while a neatly landscaped area with a stone border enhances the tranquil setting. Lush grass complements the peaceful environment.

Cottage in Sawyer

Rosie’s Cottage close to Warren Dunes (w pool)

4.9 out of 5 average rating, 70 reviews

A modern living area features a cozy sofa adorned with orange accent pillows. Two abstract paintings are displayed on the wall above, while soft lighting from two lamps creates a warm ambiance. A round table with a small green plant is positioned in front of the seating.

Apartment in Roseland

Heart of Notre Dame|King Bed|WiFi|Gym|Shuttle Bus

5 out of 5 average rating, 6 reviews

Apartment in South Haven

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

4.94 out of 5 average rating, 85 reviews

An open living space features a cozy leather sofa and a rustic wooden coffee table. Large windows allow natural light to fill the room, complemented by a ceiling fan. A pellet stove is located near the seating area, creating a welcoming environment.

Barn in Benton Harbor

Updated Pool House with Private Pickle Ball Court

4.83 out of 5 average rating, 36 reviews

An outdoor space features a sparkling pool surrounded by a concrete deck. A hot tub is positioned nearby, with comfortable lounge chairs and two shaded umbrellas inviting relaxation. The house, with a red roof, offers direct access to the pool area through sliding glass doors.

Farm stay in Baroda

Pool Open| Fire Pit | Hot Tub | Dog Friendly

4.97 out of 5 average rating, 73 reviews

An overhead view of a well-equipped kitchen displays dark cabinetry and stainless-steel appliances. A light-colored marble countertop is accented by three round stools. A cozy seating area features a pair of blue chairs, with large windows allowing natural light to brighten the space.

Tiny home in Sawyer

Sandy Feet Retreat

4.97 out of 5 average rating, 38 reviews

An outdoor lounge area features a sectional sofa surrounding a circular table. A pool is visible in the background, alongside colorful pool floats. Orange umbrellas provide shade over the seating, while green grass and paved pathways enhance the space's appeal.

Home in Buchanan

Buchanan Pool House 2 King Beds 25 min to ND