Vacation rentals with a pool in Berrien County

4.83 out of 5 average rating, 95 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 & 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

4.89 out of 5 average rating, 18 reviews

5K SqFt: Pool,Gym, Sauna, HotTub, 2 GameRms, Pets

This 5K sq ft estate, once a 1929 schoolhouse, has been transformed into our family's dream vacation home & now welcoming guests! Enjoy 7 bedrooms, a resort-style pool, hot tub, sunroom, fitness room w/ sauna, playroom, firepit, office, game & billiards rooms, a living room with an 85" TV, chef’s kitchen, dining for 20, & more. 5min to the beach & town of New Buffalo. Questions? Message me! Pool open May 30th-mid September! Pool heater down (estimated mid July). solar cover keeps pool warm!

5 out of 5 average rating, 42 reviews

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

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!

4.88 out of 5 average rating, 122 reviews

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

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.

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.

4.96 out of 5 average rating, 113 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.

4.94 out of 5 average rating, 50 reviews

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

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.

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 .

4.96 out of 5 average rating, 207 reviews

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

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!

4.96 out of 5 average rating, 105 reviews

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

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!

4.89 out of 5 average rating, 27 reviews

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.

Home in Baroda

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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Popular amenities for Berrien County rentals with a pool

Kitchen

Wifi

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.

4.83 out of 5 average rating, 12 reviews

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

NicoleRating, 5 stars4 days ago

We had a wonderful stay at this home! The girls loved their bedroom and it was close to everything. The house was even better than the pictures! Would definitely book again!

4.97 out of 5 average rating, 59 reviews

A spacious outdoor area features a heated in-ground pool surrounded by sun loungers. Umbrellas provide shade. Lush greenery frames the pool area, adding a natural touch to the landscape. The home's exterior is visible nearby, complementing the inviting setting.

Home in Bridgman

Home + Pool/Hot Tub/Fire Pit near wineries+more!

AngelicaRating, 5 stars3 weeks ago

Bridgman pool was amazing ! Elizabeth is such a great host ! The pool/Hot tub /fire pit was absolutely amazing ! We really enjoyed our family time at this location !

4.92 out of 5 average rating, 202 reviews

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

Beautiful RETREAT in the country

MelissaRating, 5 stars2 weeks ago

My girlfriends and I had a great stay! Ann’s place was peaceful and beautiful. We enjoyed relaxing outside, watching the animals and soaking in the hot tub. We will definitely be back!

4.58 out of 5 average rating, 12 reviews

Home in Stevensville

Pool Vibes Retreat | Hot Tub | Poker | Fire Pit

JeffRating, 5 stars3 weeks ago

We had a wonderful stay. The house was so clean and well appointed. There was lots of privacy and we only wish our stay was longer!

4.87 out of 5 average rating, 23 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

DavidRating, 5 stars9 months ago

We can’t wait to visit Michigan again and will definitely stay here again when we do! This place is so close to beaches, hiking and everything we wanted. Jennifer is an amazing host and was always available and very helpful! We highly recommend this home!

4.93 out of 5 average rating, 61 reviews

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.

Home in Sawyer

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

JonRating, 5 stars4 days ago

Fantastic. Between the pool, high-quality amenities (Sonos!), and the space itself, we’ll definitely be back.

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.

4.95 out of 5 average rating, 155 reviews

New Hot Tub Community pool Union Pier

JanelleRating, 5 stars2 weeks ago

I recently stayed with a few of my girlfriends for the weekend here. My friends and I absolutely loved this place. It was in a picturesque setting, and we loved how cozy it was. We especially enjoyed having the hot tub, the access to the public pool with clubhouse, and being able to walk to the beach to see the sunsets. We were able to enjoy a fire every night within the fire pit and loved being near the woods and the pond. Kristen was extremely responsive and a great host. My girlfriends and I would definitely stay again. We absolutely loved it here! Location is perfect for visiting lots of restaurants, wineries, and enjoying the best of Southwest Michigan.

4.78 out of 5 average rating, 49 reviews

A spacious deck features comfortable seating arrangements with floral cushions, complemented by a long table. An outdoor grill and fireplace are visible, creating an inviting area for gatherings. The sparkling blue swimming pool lies in the background, surrounded by lush greenery.

Home in Coloma

SouthwestMi Paradise.

EdwardRating, 5 stars7 months ago

As always Linda and Kourtney were great. Second time staying here and everything was just as awesome as the first time. Thanks again

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Condo rentals with a pool

4.7 out of 5 average rating, 10 reviews

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

Union Pier Condo with Association Heated Pool.

ChrisRating, 5 stars11 months ago

Great place just outside of New Buffalo. We would definitely stay there again. It's in a very nice and private condo complex. Place was pristinely clean and bright. It's an open first floor living area. The host was VERY responsive to all messages I sent. Nice pool in the complex and the beach on the lake is about a 15 minute walk (or you can drive there like we did). Only drawbacks are that the couch in the living area definitely needs replacing (you sink way down when you sit on it), the curtains in the bedrooms are not light blocking and the bedrooms light up soon after sunrise, and finally there's train tracks about 1/3 mile away and you'll definitely hear/feel the train in the middle of the night and in the morning (or at least we did). Nevertheless, those were minor bumps that are easily overlooked. We would rent the same place as we were impressed with it and the way the host kept it so clean. It was a very comfortable stay and I'd recommend.

4.67 out of 5 average rating, 9 reviews

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

Union Pier Condo With Heated Pool.

KellyRating, 5 stars11 months ago

Adorable place in cute Union Pier, MI. Description was spot on- place was beautiful, relaxing, nicely decorated & clean. Beach was in walking distance and was very nice - rarely too busy and epic sunsets! Loved that you could walk to the market, a fun restaurant and a bakery. It was also an easy 7-10 min drive into New Buffalo. Confirming what other reviews stated about being able to easily hear upstairs unit but honestly it didn’t bother us that much- would still come back & highly recommend!

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.

5 out of 5 average rating, 4 reviews

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

MarkRating, 5 stars11 months ago

Met expectations in every way. Clean, well maintained condo. Great location with several restaurants within walking distance, and a 10 minute walk to the beach. Beach gear was provided. Well stocked kitchen amenities and board games. Host responded quickly to all emails. Very well run. Easy all the way around.

5 out of 5 average rating, 21 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!

EmilyRating, 5 stars5 days ago

We loved our stay!! One of a kind sunsets, the beach access was awesome, and the place itself was quiet, clean, and exactly what we needed. 😊 I’ve never been to an Airbnb so well stocked before!! 15 minutes from an adorable beach town as well. Would definitely go back! 💕 thanks for having us!

A covered patio area features two chairs overlooking a marina with docked boats. Hanging ferns provide greenery, while a table adorned with a floral arrangement and a blue tablecloth adds a pop of color. The sky is partly cloudy with hints of blue.

4.6 out of 5 average rating, 5 reviews

New Buffalo Condo with Association Pool and Beach!

RichardRating, 5 stars23 months ago

I couldn't have asked for a better place to spend my vacation. The location was outstanding. Beautiful Place! The neighbors were absolutely wonderful and welcoming... they treated my family and friends as if we lived there permanently. Highly recommend!

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.

4.92 out of 5 average rating, 79 reviews

Nightingale Dunes - Modern beach town retreat

JohnRating, 5 stars2 weeks ago

Great place for New Buffalo. Close to the downtown. Place is spacious, good outdoor seating, pool is really nice.

5 out of 5 average rating, 53 reviews

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

Sunset Pointe Chalet #32: Beach + Pool+ Sports

LorenRating, 5 stars1 month ago

Nice quiet place with beautiful sunset views of Lake Michigan right from the front deck. Very peaceful and highly recommend for small family's