Vacation rentals with a pool in New Buffalo

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in New Buffalo

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

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 favorite

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 favorite

Guesthouse in Porter

4.9 out of 5 average rating, 734 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 favorite

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 favorite

Home in Stevensville

5 out of 5 average rating, 19 reviews

Private Lake, pool, hot tub, wineries & golf

Nestled among the dunes surrounded by nature and lush greenery this hidden haven boasts a private pool, and 10-person hot tub. With meticulous attention to detail, the home exudes modern sophistication, relaxation and comfort. Lots of living space inside, including a loft and pool house. Convenient area located near Grand Mere State Park, Lost Dunes Golf Club, Harbor Shores, wineries, breweries, restaurants, grocery stores and coffee shops close by. Only 30 miles to Notre Dame.

Guest favorite

Home in Three Oaks

5 out of 5 average rating, 33 reviews

Private! Cherry Beach Pool House

2024 Fall Availability! 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 favorite

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 favorite

Cottage in Union Pier

4.96 out of 5 average rating, 188 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 favorite

Guesthouse in Cassopolis

4.98 out of 5 average rating, 124 reviews

2 person cottage with pool and hot tub

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our Blackstone or fire pit. Located in a small hobby farm setting with cows, sheep, & chickens roaming the pasture. We also have a cat that claims the pool area as her own. The long driveway and gravel road are perfect for a leisurely stroll to enjoy the great outdoors. Take a swim in the pool or a soak in the hot tub and let the worries of life melt away during your stay.

Guest favorite

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.

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!

Superhost

Home in New Buffalo

4.75 out of 5 average rating, 4 reviews

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.