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Pineapple Vacations MI

Pineapple Vacations MI

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About Us

Pineapple Vacations MI offers boutique vacation rental management services across Harbor Country, with a focus on personal service and in-depth local knowledge that will make your vacation great! Our goal is to make your Michigan vacation fun, relaxing and memorable in all the best ways.

As a lifelong resident of northwest Indiana/southwest Michigan, I love Lake Michigan and I'm passionate about sharing all that our lakefront communities have to offer. I speak from the heart about our beautiful beaches, great local restaurants and the joy of experiencing our area in all seasons.

Our team is committed to the highest standards of cleanliness, as well as privacy. We communicate frequently with our guests prior to their stay to make sure every question is answered, packing lists are perfected and the best recommendations for fun and food have been made.

We appreciate your feedback and look forward to making you feel welcome!



Coastal Escape, a stunning lakefront home with private pool and hot tub, and sunset views over the lake
Main Destination, spacious luxury home with private heated pool in Grand Beach
Modern Art, a luxury getaway with private beach in Lakeside
North Star, pet-friendly home with private pool walking distance to downtown New Buffalo
Barefoot Beach, a gracious Grand Beach home with private pool and hot tub
Lake Michigan Getaway, a charming cottage with stunning views in New Buffalo
Nan's Escape, a charming beach cottage close to large private beach in Union Pier
We just might have some of the best beaches in the world!
New Buffalo public beach
No better way to spend a day than on the lake near Harbor Country
Kayak or paddle board through the Galien River Preserve all the way out to the lake!
Union Station to New Buffalo in less than an hour!
Union Pier has some of the best beaches in the area
Our sunsets are spectacular!

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