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Vacation rentals with a pool in Berrien County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Berrien County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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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

4.83 out of 5 average rating, 95 reviews

Cabin with POOL & sandy BEACH in family resort!

Relax and leave your worries behind! Enjoy the splendor of a fantastic Michigan camping experience without having to pack the kitchen sink! The cabin is located in a safe, gated community on 67 acres of wooded ravines, hiking trail, grassy areas and a small lake. Two heated pools available Memorial Day through Labor Day. Complimentary kayaks & standup paddle boards. Catch & release fishing. Pickleball, shuffleboard, sand volleyball and basketball. Enjoy crackling firepits and starry skies!

Top guest favorite

Home in New Buffalo

4.99 out of 5 average rating, 195 reviews

Designer Cottage - walking distance to downtown

Dream cottage getaway just over an hour from downtown Chicago. Walking distance from the beach, restaurants and all of downtown New Buffalo. Close to the casino, wineries and breweries. Whether driving in or taking the train, The Bradford is a relaxing yet sophisticated getaway. Eat, drink, and enjoy the beach, the pool, the shops and incredible summer sunsets, all within walking distance! Please note pool/bathhouse open late May - September and is shared with our association.Permit C22-0051

The living space features wooden walls and a pitched ceiling, allowing for natural light from tall windows. A navy blue sofa is positioned against the wall, with a coffee table in front. A dining area for four and a full kitchen are visible in the background.

Cabin in Three Oaks

5 out of 5 average rating, 42 reviews

Knotty but Nice-sleeps 6-one minute to lake

Cabin B-14 at Lakeside Cabins resorts gives you all the amenities of a 5 star resort for a 3 star price! Vacation in beautiful SW Michigan, close to Lake Michigan beach, man-made beach at Lakeside Cabins resorts, beachside towns, and wineries. Two pools, fishing, kayaks/paddleboards, shuffleboard, pickleball, volleyball and basketball too! Enjoy the peaceful setting of your cabin surrounded by trees in a park like setting of this centrally located retreat. Build memories for a lifetime!

A stone pathway leads through lush greenery and colorful flowerbeds toward a light-filled, glass-fronted structure. Towering trees create a natural canopy, enhancing the serene atmosphere of the garden setting.

Home in Three Oaks

4.88 out of 5 average rating, 122 reviews

Harbor Country Charm w Heated Pool & Hot Tub

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closes October 10, 2024 through Memorial Day 2025 After a day of exploring the waters of Lake Michigan, Warren Dunes, or nearby wineries, find your sanctuary at Mae's Place. Recharge by soaking in the inviting hot tub, sizzle up a delicious meal on the grill or in the kitchen and end the evening roasting marshmallows around the fire pit or watching an outdoor movie on the pool deck.

A spacious outdoor area is highlighted by a heated swimming pool, surrounded by lounge chairs. The two-story home features large windows and a charming façade, blending with the natural surroundings of trees. The pool depth is marked at 4 feet with a 'No Diving' sign.

Home in Union Pier

4.75 out of 5 average rating, 51 reviews

Private Hot Tub and Association Pool!

This beautiful home is impeccably furnished and the perfect getaway for your next vacation. Walking distance to several restaurants and downtown Union Pier as well as Townline beach. Your group will love the heated association pool and clubhouse just a short walk from house. A private hot tub (open year-round) in your backyard. Have your morning coffee in your screened-in porch (seating for nine) or cozy up to the wood-burning fireplace. Backyard also equipped with a firepit.

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.

4.96 out of 5 average rating, 113 reviews

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.

A charming home is set amidst lush greenery, featuring a spacious front yard and a gravel driveway. A screened-in porch invites relaxation, while the gabled roof and inviting entrance add character to the exterior. Tall trees provide shade around the property.

Cottage in Union Pier

4.94 out of 5 average rating, 50 reviews

Cozy getaway with heated pool in Union Pier

Four bedroom and two and a half bathroom, very bright and recently redone home. Large yard surrounded with old trees. We added an above ground pool in 2023. We have a pool and a hot tub. It’s perfect for two or three couples or a couple with children. Things to do: beach, biking, kayaking, antique/boutique shopping, apple/pumpkin/blueberry picking, wine tasting, brewery and whiskey distillery touring, movies, restaurants, etc. I am happy to provide more information.

Home in Union Pier

4.84 out of 5 average rating, 182 reviews

New Buffalo / Union Pier Pool Hot tub 6 Bedroom

Relax with the whole family at this peaceful home with Classic European style meets Lake Michigan! This astonishing turnkey home is the perfect escape from life in the busy city. The home is ideal for entertaining Famliy . 5 bed , 4 bath , hot tub and gas grille and( pool opens June 6) close to union pier beaches and wine country . Property is nestled in a quaint country road location 1/2 mile off re arrow highway. Room for 10 cars,blue stone patios,ping pong table .

A modern kitchen features white cabinetry and a large island with four metal stools. A stainless steel stove and refrigerator are positioned alongside open shelving displaying simple decor. Natural light enters through a window, highlighting the white tile backsplash and the artwork of a cow on the wall.

Cottage in New Buffalo

4.94 out of 5 average rating, 168 reviews

Perfect Get Away - Private Hot Tub - Lots of Room

Gorgeous, New Buffalo cottage in the heart of New Buffalo. Perfect for families and friends ~ many areas for gathering within the home. Private hot tub off the back screened in porch and only ten steps away from large community pool. Walk to everything in NB - Whittaker is only 2 blocks away. Enjoy close proximity: beach, amazing restaurants in town (Stray Dog, Redamak's, etc.). The private hot tub makes this perfect place for social distancing with Family!

An inviting outdoor pool area is surrounded by lounge chairs arranged along the deck. Trees provide natural shade nearby, and a cozy pool house is visible in the background. The crystal-clear water of the pool invites relaxation and enjoyment.

Cottage in Union Pier

4.96 out of 5 average rating, 208 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, pool, 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 and create lasting memories!

A serene association pool is surrounded by lush greenery, providing a tranquil setting for relaxation. The pool features a shallow end with a depth of 3 feet and includes stainless steel handrails for easy access. Sunlight reflects off the water, enhancing the natural surroundings.

Cottage in New Buffalo

4.96 out of 5 average rating, 105 reviews

Casa Playa New House in Union Pier w/ Private Spa

This 4 bedroom getaway is located in the heart of Harbor Country and is just a 10 minute walk or 3 minute drive to the best beach in Union Pier! Casa Playa has EVERYTHING a vacation house can offer: an association POOL, a private HOT TUB, high speed internet that accommodates many people working from home, a cozy indoor fireplace, an outdoor fire pit, an outdoor deck & grill, 2 smart Tvs, ALL brand new appliances, and games for the whole family!

A spacious backyard features a private pool surrounded by a wooden deck. Bright yellow pool floats rest on the water, while comfortable lounge chairs are positioned nearby. A charming house is visible in the background under a clear blue sky, showcasing a warm and inviting atmosphere.

4.89 out of 5 average rating, 27 reviews

The Grapes are Calling - heart of SW MI

Heart of Southwest Michigan Wine Trail! Sip and swim at this beautifully designed house off the main cobblestone street of Baroda, Michigan! Enjoy your time at the house, on the Main Street strip, weko beach, at the local wineries with live music, and so much more to do in the surrounding area! See all of our favorite things featured in the photos! Pool open Memorial through Labor Day. Winter igloo mid Nov through April!

Vacation rentals for every style

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Kick off your hiking boots at these rustic lodgings

Popular amenities for Berrien County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A community swimming pool is surrounded by a spacious concrete deck, featuring numerous lounge chairs. Lush greenery surrounds the area, providing a serene environment. The pool itself is clear and inviting, with a gradual incline for easy access.

Home in Union Pier

4.83 out of 5 average rating, 12 reviews

Modern Home, Close To The Beach,Pool,Private Spa!

A screened-in porch features a wooden hot tub, surrounded by sunlight filtering through the trees. A round glass table with two chairs is positioned nearby, providing a space for relaxation. Lush greenery and a barn are visible in the background.

Home in Buchanan

4.92 out of 5 average rating, 202 reviews

Beautiful RETREAT in the country

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

4.87 out of 5 average rating, 23 reviews

Modern Farmhouse w/ Pool Near St Joe

The inviting inground pool is surrounded by a spacious concrete deck, featuring lounge chairs positioned nearby. A Caldera spa is visible to the left, with lush greenery and trees providing a serene backdrop. The clear blue water of the pool reflects the bright sky.

4.94 out of 5 average rating, 62 reviews

Atomic Acres- POOL! SALE-20% OFF in JUNE

Top guest favorite

A spacious home is featured beside a crystal-clear pool, with a patio area furnished with several lounge chairs. Large windows provide views into the house, which showcases a charming, modern design.

Home in Union Pier

4.95 out of 5 average rating, 155 reviews

New Hot Tub Community pool Union Pier

A private pool area features a large, clear blue pool surrounded by a concrete patio. Four turquoise lounge chairs are positioned along one side, with a shaded umbrella visible in the background. Lush greenery and neighboring homes can be seen beyond the pool.

Home in Buchanan

4.93 out of 5 average rating, 14 reviews

Buchanan Pool House 2 King Beds 25 min to ND

A stylish living room features a modern leather sofa and a square coffee table. A stone fireplace sits beneath a flat-screen TV. A framed wall art displaying greetings in various languages adds an inviting touch, while an acoustic guitar leans against the wall.

Home in New Buffalo

4.92 out of 5 average rating, 12 reviews

James Dēne 11: Sunset Lake Views | Indoor Pool!

A charming exterior of a red-accented house is showcased, featuring a spacious deck with seating areas and a barbecue grill. Lush greenery surrounds the property, enhancing the sense of privacy and tranquility. Tall trees provide shade, while a clear blue sky completes the inviting scene.

Home in Lakeside

5 out of 5 average rating, 10 reviews

Cabin w/heated pool, near beach

Condo rentals with a pool

A screened-in porch features a wooden circular table accompanied by four matching chairs. A cozy seating area with blue cushions and decorative pillows is also present. Natural light filters through the surrounding trees, enhancing the serene atmosphere.

Condo in Union Pier

4.7 out of 5 average rating, 10 reviews

Union Pier Condo with Association Heated Pool.

A screened-in porch is equipped with a large dining table surrounded by six chairs. Two lanterns are positioned on the table, enhancing the space's functionality. The porch features a blend of natural light and green walls, with a comfortable seating area for relaxation.

Condo in Union Pier

4.67 out of 5 average rating, 9 reviews

Union Pier Condo With Heated Pool.

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

5 out of 5 average rating, 4 reviews

Open 7/4-7/11Perfect Location Condo Pools Walk to

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

5 out of 5 average rating, 22 reviews

Amazing Beach Condo with pool and great sunsets!

A vibrant swimming pool is surrounded by a fenced area, featuring colorful lounge chairs in shades of pink and blue. Four guests enjoy the water, with two floating on pool toys and one seated on the edge. Sunlight creates shimmering reflections on the pool surface.

Condo in New Buffalo

4.92 out of 5 average rating, 79 reviews

Nightingale Dunes - Modern beach town retreat

A heated outdoor pool is surrounded by lounge chairs, offering a space for relaxation. The pool area is bordered by a fence, with a small building for pool amenities visible. Nearby, several chalet-style units are nestled among trees under a clear blue sky.

Condo in Stevensville

4.98 out of 5 average rating, 44 reviews

Sunset Pointe Chalet #31: Beach+ Pool + Games

A heated outdoor pool is surrounded by a paved area equipped with lounge chairs. Adjacent structures feature large windows and sloped roofs, complemented by green trees in the background. The water reflects the clear blue sky.

Condo in Stevensville

5 out of 5 average rating, 53 reviews

Sunset Pointe Chalet #32: Beach + Pool+ Sports

Condo in New Buffalo

4.93 out of 5 average rating, 80 reviews

New Buffalo Getaway Condo

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