Holiday rentals with a pool in St. Joseph

4.86 out of 5 average rating, 113 reviews

A large screened front porch is furnished with several wooden rocking chairs and a wicker seating area. Natural light filters through the screens, showcasing the surrounding greenery. A small table sits centrally, creating an inviting space for relaxation and conversation.

Cabin in Three Oaks

Cabin with POOL in family resort!

Nestled within a gated 67-acre resort and just minutes from the shores of Lake Michigan, this charming cabin offers a peaceful retreat ideal for couples, families, or solo travelers, blending rustic décor with modern comforts. Guests can spend their days exploring nearby nature trails, lounging by the pool, paddling across the lake, or unwinding on the porch. The perfect vacation for exploring nearby orchards and countryside, catching live music or theater, or just slowing down and recharging!

Townhouse in Saint Joseph

This waterfront townhome features a welcoming exterior with a light blue facade and multiple balconies. Lush greenery lines the path leading to the entrance, and expansive windows allow natural light to illuminate the space, creating a peaceful atmosphere in a marina setting.

5 out of 5 average rating, 18 reviews

Michigan Harbor Townhouse with Marina Views & Pool

** Sun - Sun Rentals preferred ** Luxury waterfront townhome on the marina in Saint Joseph, Michigan w/ pool! A 5 minute drive to 3 separate beaches & downtown for restaurants, wineries, breweries, & shopping. Prime location for Harbor Shores golf course. 2 separate living rooms with televisions on all 3 floors. Beautiful 3rd floor balcony for outdoor dining. 1st & 3rd floor bedrooms have queen mattresses & their own full bathrooms. The primary bedroom has a king mattress with its own ensuite.

4.93 out of 5 average rating, 127 reviews

An inviting outdoor area is featured, showcasing a heated pool beside a vibrant garden filled with blooming flowers. Stylish lounge chairs are positioned near the pool, while a shaded bar area is adorned with ferns and colorful blossoms, creating a relaxing retreat.

Home in South Haven

The Oasis Retreat

The Oasis Retreat is a newly remodeled home with a private heated pool & hot tub, just 4 blocks from downtown South Haven & close to Lake Michigan beaches, marina, trails, restaurants, bars & shops. Perfect for families & groups, the private backyard has an outdoor bar, fire pit, gas grill, pizza oven, ping pong, outdoor shower & detached guest unit w/ seasonal bath/shower. Inside: kitchen, laundry, fast WiFi, Roku TVs, heat/AC, sleeper sofa & upstairs loft. Pool: May-Oct Hot tub: Year-round

4.97 out of 5 average rating, 121 reviews

An outdoor seating area features a cushioned sectional sofa and a wooden coffee table, overlooking a heated in-ground pool. Lounge chairs are positioned nearby, surrounded by trees, with a view of Lake Michigan in the background.

Guest suite in Miller

Beachfront- Lake Michigan-Hot Tub-Heated Pool

Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

The exterior of a two-story home is visible, featuring a welcoming front entrance. A large tree provides shade, with a swing hanging from one of its sturdy branches. Ferns line the landscape, creating a natural border around the property, complemented by a well-maintained lawn.

5 out of 5 average rating, 97 reviews

4 Bedroom home w/pool in St. Joseph

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

An outdoor dining area is featured with a large table surrounded by turquoise chairs, set against a backdrop of serene water and boat docks. A lantern sits on the table, providing a charming focal point alongside lush greenery and a view of the neighborhood.

5 out of 5 average rating, 10 reviews

Riverside Home Near Beaches, Pier, downtown

Welcome to The Harbor Hideout in St. Joseph, Michigan! Dockside, Modern riverfront retreat minutes to Lake Michigan Beaches, Piers, downtown shops, carousel and more. Sleeps 10 with 4 sleeping areas, 4 baths, and TVs in every room. Enjoy the basement game room with pool table and PlayStation, community pool & jacuzzi (open after Memorial Day), and updated modern furnishings. Perfect area for boating, relaxing, and summer fun. Open-concept living, grill, and firepit. Your ideal summer getaway!

A three-story cottage with a white exterior and large front porch, situated at the corner of Cavelier Avenue and River Run. The building features bold windows and a classic roofline, surrounded by manicured grass lawns and a well-kept sidewalk.

5 out of 5 average rating, 28 reviews

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.

4.84 out of 5 average rating, 43 reviews

A two-story Colonial home is surrounded by tall pine trees and lush greenery. The brick exterior features white shutters and a welcoming front porch with a central door. A spacious driveway leads up to the entrance, complemented by soft landscaping.

Home in Stevensville

Beautiful Colonial w/heated pool & hot tub

This 5 bedrooms, 5.5 bathrooms Colonial custom home sits on 1.37 acres of nature and tranquility featuring a private in-ground heated pool (seasonal), hot tub (all year), 3-season screened patio, fire pit, chef's style kitchen, and finished basement with wet bar. Silver Beach is ~12min drive. Great for its playground, splash pad, and amazing sunsets. Downtown St. Joseph (shops, restaurants) and Grand Mere State Park (great hiking) are 10 mins away & close to wineries and craft breweries.

4.91 out of 5 average rating, 386 reviews

Cabin in Benton Harbor

Cozy Cabin

The Cozy Cabin is a freshly renovated woodland retreat situated on 150 private acres, ideal for families, couples, or groups of friends. Sleeps up to 6 with 2 bedrooms, 1 bath, a full kitchen, Smart TV, Xbox, Wi-Fi, and board games. Enjoy wooded trails, peaceful ponds, a fire pit, cornhole, a playground, and a seasonal shared pool with paddleboats. Dog-friendly and just a short drive to Lake Michigan beaches, wineries, U-pick farms, and local attractions. Perfect for nature escapes.

5 out of 5 average rating, 244 reviews

The exterior of a two-story gray and green house is showcased, featuring a stone-accented garage and white-trimmed windows. Lush shrubs line the entrance, and a gravel driveway leads to the garage, set against a backdrop of greenery and a clear blue sky.

Home in South Haven

Driftwood Shores- September in SoHa is beautiful!

Our Summer days are all booked! Fall is starting to book up, also. 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 (9-10PM Adults only). It is included with your stay

A large outdoor pool is framed by lounge chairs and umbrellas, inviting relaxation under the sun. Adjacent, a bright living area features a blue couch, accent chairs, and a coffee table, with natural light streaming through multiple windows.

4.92 out of 5 average rating, 26 reviews

New St Joseph Resort House with POOL

Come enjoy all that Southwest Michigan has to offer in our stylish house in the Harbor Village Resort development, within walking distance to St Joseph with boutique shops, kids museum/carousel/splash pad, and beaches! Relax in the stylish decor in this new 3 br house. Soak up the sun in the large pool right across the street! The Inn at Harbor Shores Resort is also at your doorstep with -Golf - Spa - Plank's restaurant/bar, - Conference center, c - Coffee shop - Marina