Vacation rentals with a pool in South Haven

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in South Haven

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

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Guest favorite

An outdoor area features a private heated pool surrounded by a black safety fence and lush greenery. Comfortable lounge chairs are scattered around the pool deck, with a large blue umbrella providing shade. A picnic table is visible, creating a welcoming space for relaxation.

Home in Michiana Shores

4.93 out of 5 average rating, 103 reviews

Splash (Pool! Hot Tub!) at Aqua House by the Lake

Family fun in Michiana Shores. Situated on one-half acre, enjoy the private heated eco-friendly pool (open May-Sept), year-round hot tub, large yard with 2 pooldeck fire pits, Weber crafted grill, bball, ping pong, hammock, biking, and nearby tennis/pickle ball all surrounded by mature forested trees. Indoors relax with billiards, 2 flatscreens for gametime, 3 bedrooms plus pullout living room sofa, woodburning fireplace, mudroom for your stuff, and a serene enclosed patio for dining and hosting

Top guest favorite

Home in South Haven

5 out of 5 average rating, 210 reviews

Driftwood Shores- September is great for a Getaway

Great rate on our last opening for the Summer, Aug 24-27! It's time to start thinking about the fall! 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.

Top guest favorite

An indoor heated pool area is depicted, featuring a clear blue pool surrounded by colorful floaties. Comfortable seating with striped cushions lines the space. A vibrant mural of a shoreline sunset adds a decorative touch to the wall. Soft lighting enhances the atmosphere.

Home in South Haven

5 out of 5 average rating, 20 reviews

Nautical Retreat – Indoor Pool, Sauna, HotTub MORE

South Haven Nautical Retreat is a spacious 4BR/3BA home that sleeps 12, perfect for family vacations or group getaways. Just a short walk from downtown and central to both beaches, it offers endless fun for all: unwind by the indoor heated pool, relax in the 7-person hot tub, or play arcade games in the loft. Lounge in the hammock triangle, play lawn games, or enjoy cozy nights by the fire pit. Create lasting memories in the ultimate vacation retreat, with South Haven as the perfect backdrop!

Superhost

A stone pathway leads through lush greenery and colorful flowerbeds toward a light-filled, glass-fronted structure. Towering trees create a natural canopy, enhancing the serene atmosphere of the garden setting.

Home in Three Oaks

4.88 out of 5 average rating, 125 reviews

Harbor Country Charm w Heated Pool & Hot Tub

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 favorite

A spacious outdoor pool area is surrounded by lounge chairs, featuring a clear blue pool set against a backdrop of greenery and colorful landscaping. Sunlight casts a warm glow on the pool's surface, creating an inviting atmosphere for relaxation.

Condo in Douglas

4.97 out of 5 average rating, 214 reviews

Cute condo with pool great for summer fun

Beautifully updated vacation condo with gas fireplace perfect for winter escape. Close to Lake Michigan and all of the fun activities Saugatuck-Douglas has to offer. Less than 1 mile to Lake Michigan. Close to Douglas and Oval Beaches. Relax on your own front porch or walk a few steps to Isabel’s, a wonderful eatery right on site. One bedroom one bath with a cozy gas fireplace. Additional sleeping for two on pull out couch in the living room. Close to bike path to downtown.

Top guest favorite

An open-concept living space features large windows with natural light illuminating the room. A spacious kitchen with dark wood cabinetry is visible in the background, complemented by a long dining table. A comfortable sofa with decorative pillows faces the seating area, promoting relaxation.

Apartment in South Haven

4.96 out of 5 average rating, 56 reviews

Old School Condo/Loft in South Haven

Make some memories at this unique and family-friendly place. You will be close to everything when you stay at this centrally-located place. Central Lofts condos are located in downtown South Haven, 2 blocks from the summer Farmer’s Market or winter ice rink. The building has an indoor heated pool and hot tub, 2 old fashioned private movie theaters, and a fitness room. This condo has a queen bed and a pullout couch in living room. Close to town or just .7 miles to S Beach.

Guest favorite

A studio condo features a queen-size Murphy bed with a light-patterned blanket and a cozy futon nearby. A small dining area with a table is positioned adjacent to the fully equipped kitchenette. Soft blue walls and natural light create a relaxed ambiance.

Condo in South Haven

5 out of 5 average rating, 18 reviews

Private Beach/Pool on Lake MI Condo

Come unwind at this lovely condo with great amenities including private beach access, a heated pool (open during summer months), spacious patio with commercial grills. Centrally located and in walking distance to downtown South Haven. Restaurants, wine tasting, and breweries are all within walking distance. South Haven also offers expansive biking, kayak, boat rental, parks, and much more to stay as active or relaxed as you want. Come explore this unique lakeside town.

Superhost

A secluded in-ground pool is surrounded by lush greenery and landscaped gardens. Several lounge chairs are arranged near the pool, which reflects the sky above. Flowering plants and shrubs frame the scene, creating a peaceful outdoor retreat.

Home in South Haven

4.84 out of 5 average rating, 177 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 favorite

A refreshing above-ground pool is surrounded by a white wooden fence and striped umbrella. Water is gently spraying from the pool's fountain feature. Lush greenery and open fields can be seen in the background, enhancing the outdoor summer atmosphere.

Barn in Hamilton

4.95 out of 5 average rating, 130 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.

Top guest favorite

An aerial view showcases a fenced-in pool area surrounded by lush green lawns and mature trees. A small patio with outdoor seating is visible beside the pool. The gravel driveway leads to the property, with an adjacent structure and a pergola enhancing the outdoor space.

Guesthouse in Cassopolis

4.98 out of 5 average rating, 159 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.

Guest favorite

Cabin in Saugatuck

4.93 out of 5 average rating, 124 reviews

Heavenly 7 Retreat Luxury Cabin -Kingfisher Cove

Our cozy 3 bedroom, 2.5 bath luxury rustic cabin features all the comforts of home and more. Fully furnished for your comfort with towels, linens and other necessities. This cabin sleeps 8 comfortably. A heated pool and lake access are available from Memorial Day to mid September. Full-size washer & dryer in the cabin for your convenience. For larger groups, ask about availability to also rent one of our affiliated cabins nearby.

Superhost

A clear, blue heated pool is surrounded by a wooden deck, featuring a diving board and a water slide. A storage shed is visible in the background, with a life preserver mounted on the wall, under a canopy of trees.

Cabin in Benton Harbor

4.91 out of 5 average rating, 343 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.