Holiday rentals with a pool in Michigan City

Pool House near the Indiana Dunes

Open-concept home with a private heated pool May - October. Take a hike, climb a dune & run back down to the lakeshore in downtown Chesterton, a perfect getaway weekend at the Indiana Dunes. Fenced yard, grill, and cozy fire pit. Local markets, festivals, orchards, and farms. Just a few miles from the beach and national park. Saturday's European Market offers a wonderful healthy, fun, entertaining shopping & dining experience for all. Fresh produce, food trucks, mimosa brunches, and candy shops.

Guest favorite! Quiet setting w/heated pool & more

Welcome to our SW Michigan retreat! This freshly updated home in a quiet country setting feels far away from it all but is close to everything Harbor Country has to offer including beaches, dunes, breweries & shopping. With 5 bedrooms & 3.5 baths, there's enough space for your large family or multiple families to relax & enjoy plentiful amenities including heated pool (seasonal), hot tub, trampoline, fire pit, large yard, multiple outdoor dining areas, woods with paved walking path, WiFi & more!

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

Private! Cherry Beach Pool House

2025 Summer Calendar Open! Get away to Harbor County on this private ¾ acre, open concept home two blocks from Cherry Beach with a large PRIVATE heated pool and hot tub! This home has an open floor plan with natural light filling the spacious living areas. Relax in the 3 seasons room or go for a swim in a ‘15x45’ heated saltwater pool, soak in the hot tub, or roast marshmallows by firepit. New - Universal EV charger. Check our NEW listing - Warren Woods Pool Retreat!

'Pool Barn' w/Games & Hot Tub near Indiana Dunes

The Pool Barn offers a great location & unique experience. 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. pool, hot tub, grill, firepit, playground, & we are on hike/bike trail. Inside is ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 6 beds, couch, & full kitchen. *pool table is currently broken due to guests attempting attempting to move it*

Poolside Oasis - Private Heated Pool + Fun Games

Escape to our stunning 4-bed, 1.5-bath home with a private in-ground pool! Bright living spaces, a fully equipped kitchen, cozy bedrooms, and an amazing heated pool await. Conveniently located near charming Saint Joseph, Michigan, with Lake Michigan's sandy shores and vibrant downtown nearby. Indulge in local cuisine, explore nature trails, then return to the comfort of our inviting home. Your ultimate vacation experience awaits! Book now for an unforgettable getaway!

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!

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!

New Buffalo Pool/Hot-tub/Firepit

Your family will be close to everything when you stay at this centrally-located place. This five bedroom 3 bath home has it all including pool, hot-tub, firepit, fenced yard. Steps from a the association beach (small beach currently) walking distance to the large public beach, town, and marina. Renovated in 2023.