Holiday 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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Guest favourite

Cottage in New Buffalo

4.95 out of 5 average rating, 39 reviews

Luxury Cottage with pool; summer will book fast

The madrona cottage is the perfect vacation home. You will fall in love with the cottage and the location, New Buffalo is amazing. The home has 4 full bedrooms and 3.5 baths. It will sleep 8 guests easy. Everything you need to enjoy a nice vacation is included in the place. The cottage has been completely rehabbed with all spaces being brand new. It's has a heated pool and is close to the beach. Relax by the fire or enjoy the game room with a pool table, card table and games. Great for families.

Guest favourite

Home in Stevensville

5 out of 5 average rating, 52 reviews

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!

Guest favourite

Cottage in Union Pier

5 out of 5 average rating, 28 reviews

Heated pool & private hot tub!

Modern 5 bedroom 3.5 bath home with private hot tub is perfect for large groups, families, couples getaways, and corporate retreats. Soaring ceilings open concept space provides plenty of room for gathering. Access to association heated pool (open late May thru Columbus Day) and clubhouse. Short walk to Townline Beach, farmers market and all that Union Pier has to offer. Enjoy the fire pit for s’mores and the private hot tub out back making this the perfect home for vacationing in all seasons.

Guest favourite

Guesthouse in Porter

4.9 out of 5 average rating, 746 reviews

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

Pool and hot tub are open! 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. Lots to do at the 'Pool Barn' too. Outside is pool, hot tub, grill, firepit, playground, & we are on hike/bike trail. Inside is billiards, ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 6 beds, couch, & full kitchen. No cleaning fee!

Guest favourite

Home in Chesterton

4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

Open-concept home with a private heated pool. 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 favourite

Home in Three Oaks

5 out of 5 average rating, 33 reviews

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!

Guest favourite

Home in St. Joseph

4.96 out of 5 average rating, 24 reviews

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 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!

Guest favourite

Cottage in Union Pier

4.96 out of 5 average rating, 191 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!

Guest favourite

Cottage in New Buffalo

4.96 out of 5 average rating, 100 reviews

Casa Playa New House w/ Private Spa & Pool Access

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!

Guest favourite

Home in Sawyer

5 out of 5 average rating, 23 reviews

The Summer House - Heated Pool - Steps to Sawyer

Welcome to the Summer House! Our newly renovated private home featuring a heated pool is located steps to downtown Sawyer; just a 3 minute drive to Warren Dunes State Park. Enjoy all Harbor Country has to offer while staying in your own home walking distance to coffee, restaurants, and shops! Guest will have access to a private gated pool and parking right in front of the house for four vehicles.

Guest favourite

Home in New Buffalo

5 out of 5 average rating, 30 reviews

Vintage restored home, pool/hot tub-walk to town

Heated pool opens May 1!! Welcome to Harbor Country. This incredible, completely renovated, charming colonial home is in an ideal location-blocks from everything- town, restaurants & beach. Stunning finishes throughout & outside courtyard is phenomenal with pool, hot tub, firepit & outside shower. Parking for 4 cars. Overflow city parking at Willard and Mechanic (block away)

Superhost

Home in Lakeside

4.8 out of 5 average rating, 10 reviews

New renovated house, private heated pool sleeps 10

Experience Lakeside luxury in our newly renovated 4BR/2BA house with a brand new pool, patio, and stunning indoors, and beautiful landscaping. Sleeps 10 with a private heated pool, fire pit, BBQ, and Flat screen TVs. Just minutes from Union Pier beach, and close to brew-pubs, wineries, restaurants, and golf. Book now and enjoy a dream vacation!