
Vacation rentals with a pool in Michigan City
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Michigan City
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Michigan City rentals with a pool
House rentals with a pool

Splash (Pool! Hot Tub!) at Aqua House by the Lake
Greg is an amazing host. Beautiful walkable area, full of nature. The pool and pool table provide hours of entertainment. Top notch Airbnb. Would definitely recommend.

Private Cabin Retreat - Heart of Harbor Country
Loved our stay! The house was very nice and clean

Comfy Cottage-Heated Pool, 1 Block to Beach!
Brent's place is really nice as described. very quiet and peaceful neighborhood. the home itself is cozy, clean and well decorated. the treehouse is good but not warm enough for cold months. finally the wifi is good in the house but no signal on basement bedrooms. All in all we had a wonderful time in Michiana and we will look to back again in summer months.

Modern Lake House w/ Private Pool near New Buffalo
A party of 10 women for a bridal party weekend before the wedding festivities. Plenty of room for everyone lots of big bathrooms so much open space. The pool was warm the hot tub was bubbling. Such an amazing place set in the Sand dunes a five minute drive to Lake Michigan, and a short walk to the small lake, we enjoyed all of the amenities and had a wonderful time.

Secluded Pool Playhouse: Hot Tub, Games, Fire Pit
The home is very spacious, clean and very well stocked. Kitchen had everything we needed to cook indoors and outdoors. Plenty of towels and bedding. We enjoyed the hot tub and would love to make a trip in the summer to enjoy the pool. Play room was enjoyed by family members of all ages. Communication with owners was great.All questions and concerns were answered promptly and very accommodating. Would highly recommend this home. We didnt want to leave!

Pool House near the Indiana Dunes
The location was so peaceful and close to everything (10 mins from the dunes). The house was comfy and had everything you could possibly need. Melissa thought of everything! The pool.. OMG the best! The heater made the water PERFECT! Made it even more special that we could bring our dogs. The fully fenced yard was perfect. Will definitely be coming back.

NEW! 1BR Cottage w/ Pool, Firepit, Walk to Beach
Truly lovely spot to stay! I needed a solo weekend away within a few hours drive of home (Indy) and this proved to be a great choice. The finishes are considered and done well in every space. I came here to write and relax, and that’s indeed what happened. I worked in comfort, took aesthetic snaps on my snack breaks, and rested. The bed is delightful. The place is quiet and well appointed; great location, easy in and out/parking. The listing says there are no TVs, but in fact there are two Samsung Frame TVs in the Ivy. Nice touch. Also was lovely to be able to wash my swimsuit in the laundry before going home. Would gladly stay here again and would love to rent multiple cottages with friends.

New Hot Tub Community pool Union Pier
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.
Condo rentals with a pool

Union Pier Condo with Association Heated Pool.
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.

Union Pier Condo With Heated Pool.
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!

Perfect Location Condo w/Marina Views Pools Walk t
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.

Amazing Beach Condo with pool and great sunsets!
Let me begin by saying we can’t wait to stay again. The location was absolutely amazing, particularly if you, like us, adore sunsets. We enjoyed the walk to the beach which is on the property and found the sunsets breathtaking. The beach is beautiful and allowed us to walk three miles. The unit was very clean and had what we needed. We were able to cook in two nights and enjoy a Saugutuck restaurant one evening. Patricia was very communicative and was prompt in responses to questions. We simply could not have enjoyed a better stay. We look forward to coming back.

New Buffalo Condo with Association Pool and Beach!
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!

Nightingale Dunes - Modern beach town retreat
This Airbnb was so nice and so much bigger than we thought it would be! The first floor has a bedroom with a king bed and bathroom across. Upstairs has another room with a king bed and a room labels as an office but actually a double bed so plenty of private sleeping places as well as the loft area. The futon was very comfortable to sleep on too. It took about 10 minutes to walk downtown New Buffalo which was exactly what we wanted. The other direction had a local shop called The Farmette that you can drive or walk to - it was the cutest place to visit. While it was too cold for the pool when we were there, it is an awesome and convenient amenity and it’s right outside of the patio. We had 6 girls and more than enough room for a weekend stay. Would highly recommend!

Sunset Pointe Chalet #32: Beach + Pool+ Sports
We absolutely loved this place and our stay. The lake views were more beautiful than the photos could show, the chalet is comfortable and well-stocked, and there was so much to do in the community that we didn't even scratch the surface. We loved the beach area which wasn't crowded at all, even on Labor Day weekend. We drove in to St. Joseph for dinner and to go to ur favorite shops - super easy drive. The walk to the beach was so short we didn't even take a lunch out there, just popped up to the house whenever we needed a restroom break or a snack. We never needed to contact Ben but got plenty of communication beforehand and the manual in the house provided info of how to text him if we needed to. We would definitely stay here again, highly recommend!

New Buffalo Getaway Condo
Our stay here in New Buffalo was perfect! We attended our daughter’s college graduation and it was a perfect place to come back and relax at. We enjoyed an amazing restaurant and walks on the beach. We highly recommend!
Quick stats about vacation rentals with a pool in Michigan City
Total rentals
150 properties
Total number of reviews
1.8K reviews
Family-friendly rentals
140 properties are a good fit for families
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
150 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Warren Dunes State Park
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- University of Notre Dame
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Willis Tower
- Wicker Park
- Potato Creek State Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Chicago Cultural Center