Vacation rentals with a pool in Van Buren County

Driftwood Shores-SH is a great fall getaway!

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.

Harbor View-New 6-person LSV/Golf Cart included

Nestled along the shore of Lake Michigan, a brand-new, five-bedroom pet-friendly house offers a perfect blend of natural beauty, outdoor adventure, and cultural experiences. South Haven's pristine sandy beaches, lighthouses, and picturesque sunsets make it a haven for relaxation and rejuvenation. You can explore the downtown area with its unique shops, galleries, and restaurants, embark on outdoor activities like hiking, biking, and water sports, or relaxing at one of the two neighborhood pools.

Nautical Retreat – Indoor Pool, Sauna, HotTub MORE

Chill & Thrill 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!

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

Walk everywhere: Bikes: Pool & hot tub: Beach gear

✨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 🚲 4 beach cruiser bikes included 🛍️ 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 inte

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.

Lamb Guest | Private Pool, Hot Tub, Cabana, Dogs

Welcome to Lamb Guest, where lakeside luxury is defined. Spanning three floors, the home offers multiple living spaces and game rooms for relaxation or entertainment. Gather around the grand dining table, which comfortably seats 12. With 2 bedrooms on the main floor and 5 upstairs, there's space for everyone. Step outside to a resort-style backyard featuring a pool house and hot tub. 0.6 miles to South Beach Blue Stairs and Kids' Corner Park. 1.3 miles to downtown South Haven! Dog friendly!

Old School Condo/Loft in South Haven

Make some memories at this unique and family-friendly place. You will be close to everything. Central Lofts condos are the converted South Haven Central High School, built in 1913 and 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, an old fashioned private movie theater, 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.

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.

Beach-Themed Game Room & Pool Near Lake Michigan

The Northern Anchor: Year round community pool & hot tub! The ultimate family getaway! 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.

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.

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.