Vacation rentals with a pool in St. Joseph

Driftwood Shores/SH Fall colors & a beautiful lake

September and Fall is starting to book! 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. NOTE: AirBnb has changed its pricing structure so that now the host pays the 15.5% service fee (instead of the guest.) Your overall cost hasn't changed, but the nightly rate reflects this new payment system.

Heated Indoor Pool & Tennis/Pickleball Court!

Fabulous Union Pier home with heated indoor pool & private combination tennis/pickleball court! Escape from the city life to Asolare, the upscale 4 bedroom, 4 bathroom vacation home located just couple blocks from lake Michigan beach. This 3800 sf villa host up to 16 lucky guests & provides a multitude of amenities to make for a trip you will never forget! Accommodations include private beach rights, indoor pool, tennis & pickleball court and supplies, sauna, billiard, screened porch & fire pit.

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, private resort-style neighborhood pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax & 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!

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.

Downtown Loft: Indoor Pool, Hot Tub, Gym, Theater

Central Lofts condos used to be the old Central High School. We are located in downtown South Haven. Stay 2 blocks from the Farmer’s Market, also an ice skating rink in winter. The building has a shared indoor pool and hot tub, 2 old fashioned private movie theaters (seats 12), fire pit, and an exercise room. This cute condo has a king bed and twin sized trundle bed in master bedroom, and two pullout couches in living room. Walk to town & the beach, .7 miles to S. Beach and 2 blocks to town.

Awesome Family Escape with pool and private beach

Fun summer getaway with the family or a group of friends at this hidden gem in Southwest Michigan! This peaceful condo features 2 bedrooms with 3 brand-new beds(1 king and 2 queen) comfortably sleeping 6, and 2 full bathrooms. Equipped with two work-from-home desks and high-speed internet, it’s perfect for balancing work and relaxation. Enjoy the full kitchen, washer and dryer, cable TV, and all you need for fun!! Relax on the private beach, just a short walk or hang at the private pool.

Atomic Acres- Pool, Hot tub, Fire pit & more

Atomic Acres is a remodeled, 4 bedroom/3,000 sq ft home in the heart of Harbor Country in Sawyer, MI. This home sits on 5 beautiful acres with a fenced in side yard and open back yard with a wandering creek along its border. The amenities are endless: fire pit, seasonal pool & hot tub, patio, ping pong table, pool table, screen porch and more! An aesthetic nod to the mid century era is felt throughout with pieces curated to appeal to the vintage, and all so close to Warren Dunes (1 mile)!

Cozy Ranch | Huge Fenced Yard| Fall Fun

Escape to a peaceful area of SW Michigan, while being close to everything. Minutes from Warren Dunes and Weko beach, this 3 bedroom ranch home is the perfect fall getaway. Outside, enjoy a large fenced yard, with picnic table, fire pit, lounge chairs, and plenty of space to spend time together. Behind the property, two acres of woods offer a quiet backdrop and a beautiful place to experience the colors of fall. Located near lots of dining, breweries, wineries, orchards, and local farms.

Play @ The Hideaway - hot tub, sauna, gymnasium

Accommodating up to 22 guests, this expansive 5,891 sqft property is set on 22.6 acres, creating a private oasis complete with a pool, hot tub, sauna, and gymnasium. The residence features a Great Room, fireplace, fire pit, and a private trail, making it an ideal setting for relaxation and recreation. With 3 king-size beds, 4 queen-size beds, and 2 bunk beds with trundles, comfortably catering to the needs of large groups. This venue offers enjoyable experiences for guests of all ages.

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Beautiful home in the heart of Beachwalk, across the street from Lake Kai, pools, basketball & tennis courts and 2 blocks to Lake Michigan. This home is bursting with charm. Front porch runs the width of the house. Dining area opens up to family room with a lovely fireplace. Stunning master bedroom w/walk-in closet and beautiful new bathroom with all the finishes. 3 more bedrooms upstairs, one with full bathroom attached and the other 2 sharing bathroom. 5th bedroom on the lower level.

Indoor pool & hot tub: Walk everywhere: Gym

✨Upscale historic loft building 🚶WALK EVERYWHERE 🕑 2:00 PM CHECK-IN ⭐️Central Loft amenities⭐️ ♨️ Hot tub 🏊‍♂️ Indoor heated pool 🎬 2 movie theaters 💪 Workout room 🏖️ Beach necessities included 🌊 1/2 mile to Lake Michigan 🛍️ A block from downtown SoHa 🍷 Near The Lakeshore Wine Trail 🍺 Close to several breweries 🧺 Washer & dryer in condo ☕️ Keurig & standard brewing coffee pot 🧑‍🍳 Fully stocked kitchen ⚡️ High speed internet 📺 Smart TV

Lakeside with heated pool & pvt beach access!

LAKESIDE COTTAGE - POOL, HOT TUB & RARE semi-private Lake Michigan access to gorgeous beach shared by just 10 homes, so it’s never crowded! Beach access is a 7-min walk away (no parking). The pool will close Sept 16th, 2027 this year! Charming, sun-filled cottage sleeps 8 (3BR + pull-out). Heated 85 degree pool (May 22–Sept 15), new hot tub, fire pit, gas fireplace, spacious deck, bluestone patio & grill. 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!