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Fire Pit | Walk to Beach, Kids Park & Downtown

Welcome to Seasons of South Haven Rentals, a collection of family owned, operated and custom designed vacation homes where creating memorable experiences and spoiling our guests is what we love most! Escape to cozy Ashwood Cottage centrally located in beautiful South Haven within walking distance to stunning beachfront views of Lake Michigan (2 blocks), kids plash pad (5 blocks), Kids Corner playground (1 block) and downtown (6 blocks). This fully renovated home is perfect for a family vacatio

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.

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

Cozy Cabin in the Woods

Just under two hours from Chicago and only 1/2 mile from Hagar Beach, this beautifully updated 100-year-old cabin offers a peaceful retreat in the woods. Surrounded by tranquil landscapes and towering trees, you’ll enjoy the perfect blend of rustic charm and modern comfort. Tucked along a quiet dirt road, the cabin is ideally located 15 minutes from South Haven and 10 minutes from St. Joseph making it close enough for dining, shopping, and activities, yet far enough to unwind in nature’s calm.

BLueVieWToo/STePS to The BeaCH/LaKE VieWS/Downtown

TOES IN THE SAND/STEPS TO THE BEACH/WATER VIEWS FROM THE DECK! Attractive 2 bedroom cottage (500 Sq. Ft.) located adjacent to Packard Park with it's sandy beach. Bring your flipflops and head to the water! Living space, 2 beds/1 full bath/a beautiful kitchen w/ Washer/Dryer. Large deck to sit and relax and watch the sunset. Wifi, TV, Beach chairs, umbrellas, toys, towels, BIKES included Come be at home with us! Not just a rental, this is a home! **ADJACENT 4 BED HOUSE ALSO AVAILABLE**

Modern Secluded Cabin, Private Hot Tub, Fire Pit

Escape to this charming cabin in the woods. Relax in total privacy and peace and quiet with majestic views of towering trees. Natural sunlight floods into the home creating a healthy environment to unwind in. Stay warm and cozy with heated concrete floors and a gas fireplace. Cook in the well stocked kitchen. Soak away your worries in the private hot tub. Roast s’mores in the backyard fire pit and grill on the huge deck. Fun awaits in the 3-season game room in barn NOT HEATED. Dog friendly.

Captain's Loft in the heart of South Haven

Located in the heart of downtown South Haven! We are steps from Lake Michigan, South Beach, the Black River, Restaurants & Shopping. Recently updated with new sofa, queen bed & fresh beach vibe! An upstairs unit, its 25 steps to a perfect getaway that is close to everything that downtown South Haven has to offer! Private access to a rooftop deck with showstopper views of the river & marina. 1-bedroom with a private entrance from the sidewalk, a small kitchen, bathroom, and living room.

Panoramic Views/Beach/Hot Tub/Sauna/Cold Plunge

Welcome The Windover! • Private Beach • Panoramic Lake Michigan Views • Hot Tub, Sauna, Cold Plunge, Outdoor Shower •Expansive Yard /Outside Activities • 4 minutes to downtown St. Joseph, The Benton Harbor Arts District, and Harbor Shores • Centrally located Close to 6 Local Beaches Fine and Casual Dining World Class Golfing Wineries Breweries Nature Parks Mountain Bike Trail Park 1/4 from Property Curious Kids Museum Compass Fountain Silver Beach Carousel St. Joseph Lighthouse

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.

Family Friendly Private Beach Home with Hot Tub

5 min walk to Private Beach 10 min drive to Downtown South Haven 18 min drive to Downtown Saugatuck Escape to our 3BR South Haven home in an exclusive community, just a 5-min walk to a private Lake Michigan beach. Comfortably sleeps 8. Features a private hot tub, chef's kitchen, and cozy fireplace. Perfect for families, you're just a short drive from downtown South Haven & Saugatuck. Your luxurious lakeside retreat awaits! Experience South Haven With Us & Learn More Below!

Benchbike,hottub,playground,3blks to beach,firepit

3 bedroom, 2.5 bath home, 3 blocks from Lake Michigan, 2 blocks to Kids Corner playground, 10 min walk downtown. 6 person hot tub! Super fun bench bike! Outdoor firepit All deluxe memory foam mattresses. 2 kings, 2 fulls, 2 twins. Sleeps 8 adults comfortably, 10 sharing full beds. Enjoy bikes (including bike for 2, bench bikes), 2 kayaks, picnic supplies, books, toys, and games. Foosball Giant Kerplunkit game Board games Kid and pet friendly. Sledding, iceskating nearby

Modern Log Cabin With Hot Tub Near Lake Michigan

Welcome to our serene South Haven cabin. An elevated retreat where modern design meets a calm, grounding sense of escape. Thoughtfully styled to help you unwind and recharge, the space offers a quiet, effortless luxury you’ll feel the moment you arrive. Secluded yet convenient, you’re just 5 minutes from downtown South Haven and 4 minutes from North Beach. Perfect for days of lakeshore adventure and evenings of relaxed indulgence.