Holiday 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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Top guest favourite

Home in South Haven

5 out of 5 average rating, 203 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.

Superhost

Home in Three Oaks

4.88 out of 5 average rating, 123 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.

Guest favourite

Home in West Olive

4.97 out of 5 average rating, 145 reviews

Available 7/5-12 - Mini Resort Indoor Pool&Sauna

Availability JULY 5-12 3 night minimum July 5-12 Aug 9-17 Aug 20-31 Sept 1-23 Book for Christmas! *NO PARTIES &no persons outside of your originally contracted group may visit the property during your stay.* This property is a perfect getaway situated between Holland, Grand Haven & Grand Rapids right on Lakeshore Dr. Our home sits up on a hill overlooking a beautiful 6 acre pond. You will feel as though you are at your own personal resort w/private heated indoor pool & sauna for 6!

Top guest favourite

Apartment in Douglas

4.97 out of 5 average rating, 208 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 favourite

Flat in South Haven

4.98 out of 5 average rating, 51 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.

Top guest favourite

Apartment in South Haven

5 out of 5 average rating, 84 reviews

SunKissed Sanctuary + Pool + Hot Tub +CentralLofts

A stylish, historic lower-level loft featuring exposed brick and ductwork paired with true floor-to-ceiling walls for much-needed privacy. Designed by a family for families, this South Haven retreat blends charm, comfort, and convenience in a walkable location close to South Haven's countless activities. Amenities at Central Lofts include year-round access to a pool and hot tub, a fitness room, and seasonal access to a spacious shared patio with three grills.

Superhost

Home in South Haven

4.84 out of 5 average rating, 174 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

4.95 out of 5 average rating, 126 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 favourite

Guest house in Cassopolis

4.98 out of 5 average rating, 158 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 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 favourite

Cabin in Saugatuck

4.93 out of 5 average rating, 120 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

Cabin in Benton Harbor

4.91 out of 5 average rating, 335 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.

Guest favourite

Home in Douglas

4.98 out of 5 average rating, 136 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!