Holiday rentals with a pool in Benton Harbor

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Benton Harbor

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

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Guest favourite

Home in Bridgman

4.91 out of 5 average rating, 127 reviews

Epic Indoor Pool w/slide & hot tub close to beach

Escape to Vine Vista, a 3+ acre retreat near Lake Michigan beaches, wine & beer tastings & the third coast. Enjoy a large private indoor heated pool (larger than many hotels!) & hot tub. Accommodates groups of up to 25. You can see why it will be featured in the Emmy Award-winning show Staycation as one of the highlights of the area. Unwind in privacy, but close to local attractions. Dining accommodations for family reunions, birthday celebrations, holidays or bachelor/bachelorette parties.

Top guest favourite

Home in South Haven

5 out of 5 average rating, 219 reviews

Driftwood Shores-Beautiful Fall Days are Here!

It's time to start thinking about the fall! Great September weekday rates! How about a golf trip? Enjoy a trip to beautiful South Haven along the shores of Lake Michigan. Driftwood Shores is a charming 1,680 sq. ft. home in the Harbor Club Resort. It has everything you need to enjoy a peaceful family vacation, friends getaway, or girls weekend out. The Resorts Indoor/Outdoor Pool with retractable roof and outdoor hot tub is open year around from 7 AM to 10 PM. It is included with your stay.

Guest favourite

Home in Three Oaks

4.88 out of 5 average rating, 133 reviews

Harbor Country Charm w Heated Pool Open Til 10/12!

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closes October 10, 2024 through Memorial Day 2025 After a day of exploring the waters of Lake Michigan, Warren Dunes, or nearby wineries, find your sanctuary at Mae's Place. Recharge by soaking in the inviting hot tub, sizzle up a delicious meal on the grill or in the kitchen and end the evening roasting marshmallows around the fire pit or watching an outdoor movie on the pool deck.

Top guest favourite

Cottage in Union Pier

4.96 out of 5 average rating, 218 reviews

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private 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! Create lasting memories!

Superhost

Home in Union Pier

4.84 out of 5 average rating, 190 reviews

New Buffalo / Union Pier Pool Hot tub 6 Bedroom

Relax with the whole family at this peaceful home with Classic European style meets Lake Michigan! This astonishing turnkey home is the perfect escape from life in the busy city. The home is ideal for entertaining Famliy . 5 bed , 4 bath , hot tub and gas grille and( pool opens June 6) close to union pier beaches and wine country . Property is nestled in a quaint country road location 1/2 mile off re arrow highway. Room for 10 cars,blue stone patios,ping pong table .

Superhost

Home in South Haven

4.84 out of 5 average rating, 184 reviews

Experience Nature-Charming Cottage

Romantic getaway and/or family adventure Quiet updated farmhouse on a quiet road 5 miles from South Haven and Lake Michigan.The Black River runs along the property and there are 3 ponds.There is secluded in ground pool,woods and landscaped grounds for walks Great local markets A guest made a video about his time at the cottage that you can see on You Tube. GoozyVision Trip to South Haven,Michigan July 2017 The video also shows the beach and the town

Top guest favourite

Barn in Hamilton

4.96 out of 5 average rating, 147 reviews

The Garden House Cottage at Redbud Farm

It's summer at Redbud Farm! The Garden House Cottage is a beautifully remodeled old farm barn. Modern boho farmhouse style. This place has charm galore. You'll love the peace and quiet of the country and the gardens are professionally landscaped and maintained. Enjoy the views of the English potager style garden right out the window while relaxing on the queen bed. Traveling with friends/family? Check out my other listing The Granary at Redbud Farm.

Guest favourite

Guest house in Porter

4.89 out of 5 average rating, 799 reviews

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

Heated pool open until mid October!Hot tub open all year! The Pool Barn is only 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. Outside enjoy our 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, 5 beds, couch, & full kitchen. Book today!

Top guest favourite

Guest house in Cassopolis

4.98 out of 5 average rating, 165 reviews

Quiet 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 sheep roaming the pasture. We also have a couple cats that claim the pool area as their 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.

Superhost

Guest house in Michigan City

4.86 out of 5 average rating, 157 reviews

Lagunitas Coach House in Beachwalk, Lake Michigan

Lagunitas Coach House is a sought after location on the quaint Thomas blvd cul de sac. It is the coach house to Gooch Life. It is the perfect get away spot for a couple or small family wanting to escape to the beautiful beach of Lake Michigan. Lagunitas and Gooch Life share the property but are separate structures. Lagunitas has a private entrance, amenities, and parking. Lagunitas sleeps 6, see pictures for bed configuartion.

Superhost

Cabin in Benton Harbor

4.9 out of 5 average rating, 355 reviews

50 Private Acres w/ Trails & Pool: Cozy Cabin

Unwind in this freshly renovated cabin set on 50 acres of peaceful nature. Explore private walking trails, relax by two serene ponds, or cool off in the seasonal pool (shared with our family). The space includes a kitchen for cooking, Xbox One for movie nights, and a fire pit perfect for stargazing. Dog-friendly and ideal for a quiet escape into the outdoors—with all the comforts of home.

Top guest favourite

Home in Douglas

4.98 out of 5 average rating, 144 reviews

Rustic Mid Century Pool Oasis. Steps from town!

Located just under 5 minutes from downtown Saugatuck and 2 minutes from downtown Douglas, the Green Oasis is your sanctuary away from home. Sitting on 3.5 acres of lush green landscape, this is the perfect spot for relaxation, while still having access to all of the amenities of Saugatuck / Douglas / Fennville...... and OMG the pool!