
Vacation rentals with a pool in St. Joseph
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Top-rated rentals with a pool in St. Joseph
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Designer Cottage - walking distance to downtown
Dream cottage getaway just over an hour from downtown Chicago. Walking distance from the beach, restaurants and all of downtown New Buffalo. Close to the casino, wineries and breweries. Whether driving in or taking the train, The Bradford is a relaxing yet sophisticated getaway. Eat, drink, and enjoy the beach, the pool, the shops and incredible summer sunsets, all within walking distance! Please note pool/bathhouse open late May - September and is shared with our association.Permit C22-0051

The Northern Anchor: Your Perfect Getaway!
The new enclosed subdivision pool & hot tub are now open! Enjoy our beautiful vacation house. Fully furnished with loads of thoughtful details. Perfect for families with kids or for groups/individuals looking for a relaxing get away. Close to everything: beaches, downtown shopping, wonderful restaurants, award winning golf courses, pick your own orchards, beautiful wineries and much more. Visit us year round - from snowy woods to sandy beaches - the Northern Anchor has something for everyone.

Harbor Shores House with Bunk Beds and Pool!
Escape to a tranquil retreat in this 3 bedroom cottage in Harbor Village, where comfort and convenience await. You'll love being situated in the Harbor Shores neighborhood, where downtown St. Joseph and Benton Harbor’s quaint shops and restaurants are just a short walk or bike ride away. The home enjoys stunning views of the marina and golf course from the front porch and terrace accessible via the master suite. Swim and/ or relax at the pool located steps away - right across the street.

'Pool Barn Camper' w/Hot Tub near Indiana Dunes
Heated pool open until mid October! Hot tub open all year! Fully equipped RV sleeps 5, has bathroom w/shower, stove, microwave, TV, heat & A/C, & running water all year. Located on the bike trail & only minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hike in the Indiana Dunes National Park along the Little Calumet River & the historic Bailley homestead, only 1 block from the RV. Enjoy our large pool, hot tub, grill, campfire, & playground too. Schedule your visit today!

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.

Cozy condo with fireplace perfect for fall fun.
Beautifully updated vacation condo with association pool perfect for summer or fall vacation. 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.

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!

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 .

Wabi Sabi Chic at The Flamingo Ranch in Lakeside
Autumn at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. Equal parts sanctuary and playground, this designer-owned haven offers both deep seclusion + an open-format layout that invites connection, healing + memory-making. Whether you’re gathering with family, reuniting with old friends, or seeking a rejuvenating escape, we deliver an experience that’s as comfortable + stylish as it is energetically charged.

Country cottage with hottub for two!
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.

Marina Sunset: Savor Fall Flavors in Saint Joseph
Located in the beautiful beach town of Saint Joseph, Michigan, this brand new waterfront townhome is located within Harbor Shores Resort. The area's natural beauty can be seen throughout several dunes areas and beaches nestled on the southeast corner of Lake Michigan. Enjoy wineries, award winning breweries, and an abundance of restaurants. There are adventures abound with boating, fishing, hiking, and biking all nearby.

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.
Popular amenities for St. Joseph rentals with a pool
House rentals with a pool

Fall Fun in MI! Heated Pool, Hot Tub, Game Room

Beautiful home with Beach views in Beachwalk

Experience Nature-Charming Cottage

Modern Lake House w/ Private Pool near New Buffalo

Hot tub open year round and pvt association beach!

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Private! Warren Woods Pool Retreat

Rustic Mid Century Pool Oasis. Steps from town!
Condo rentals with a pool

Lake Effect Loft +Beach+Downtown+Pool+Hot tub

Union Pier Condo with Association Heated Pool.

Northern Lights 2 Bed 2 Bath With Pool

Fall 2 nt min Perfect Location Condo Pools Walk to

South Haven North Shore condo

Amazing Beach Condo with pool and great sunsets!

Schoolhouse Suite: Indoor assoc. pool, hot tub!

Nightingale Dunes - Modern beach town retreat
Other vacation rentals with a pool

Lux Cabin Twin Peaks East • Private Pool & Hot Tub

Luxury home with pool.

The Grapes are Calling - heart of SW MI

Old School Condo/Loft in South Haven

Modern Farmhouse w/ Pool Near St Joe

Indoor pool & hot tub•Great location•upscale•bikes

Riverdance - Heated Pool Open 5/13-10/9

Downtown Loft: Indoor Pool, Hot Tub, Gym, Theater
Quick stats about vacation rentals with a pool in St. Joseph
Total rentals
20 properties
Nightly prices starting at
R1,912 ZAR before taxes and fees
Total number of reviews
300 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Warren Dunes State Park
- University of Notre Dame
- Washington Park Zoo
- Silver Beach Carousel
- Potato Creek State Park
- Saugatuck Dunes State Park
- Bittersweet Ski Resort
- Woodlands Course at Whittaker
- Saugatuck Dune Rides
- The Dunes Club
- Lost Dunes Golf Club
- Point O' Woods Golf & Country Club
- Elcona Country Club
- South Bend Country Club
- Warren Golf Course
- Kennedy Water Park
- Fenn Valley Vineyards
- 12 Corners Vineyards
- Cogdal Vineyards
- Shady Creek Winery
- Dablon Winery and Vineyards