Holiday rentals with a pool in Benton Harbor

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.

Amazing Beach Condo with pool and great sunsets!

Unwind with your family at this peaceful getaway! This cozy retreat features 1 bedroom, 1.5 bathrooms, and a pull-out couch in the living room. Enjoy exclusive access to a private beach and a community pool reserved for the condo association. Relax on your private deck while taking in breathtaking sunsets, just a short 5-minute walk from the beach! Located between South Haven and St. Joseph, Michigan, this charming spot offers easy access to local wineries, nature centers, parks, and more!

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!

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

Waterfront property with a private hot tub, pool, and tennis court, making it an ideal destination for those seeking both relaxation and recreation. Visit beautiful Southwest Michigan and stay at the St. Joe Overlook. Take a swim in the pool, unwind in the hot tub, take the kayaks out for a river cruise, or sit by the fire. Enjoy this stunning location and top-notch amenities. A trip to the St Joe Overlook is the perfect place to gather & reconnect. Maximum Guest Count 16.

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 .

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.

Experience Nature-Charming Cottage

Romantic getaway and/or family adventure Quiet updated farmhouse on a quiet road 5 miles from South Haven and Lake Michigan.The Black River runs along the property and there are 3 ponds.There is secluded in ground pool,woods and landscaped grounds for walks Great local markets A guest made a video about his time at the cottage that you can see on You Tube. GoozyVision Trip to South Haven,Michigan July 2017 The video also shows the beach and the town

Driftwood Shores-Enjoy a Winter Getaway!

South Haven is a great place for a Fall or Winter getaway! 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. It is included with your stay.

Cozy cottage for two with hot tub!

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.

Family Tides at Harbor Shores

The ultimate family retreat awaits at this 3BR townhouse, boasting captivating marina views. Unwind in comfort with two restful king beds for a good night's sleep after family adventures. Explore charming cafes, exciting water sports, golfing, and Silver Beach. Embark on riverside strolls along the paved walkway, let the kids splash in the inviting heated pool, and stay seamlessly connected with fast Wi-Fi.

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.

Story Book Escape, Skiing Close, Magical, Clean

Escape to this private, renovated bungalow for two, nestled in nature. Perfect for a quiet retreat, it features a dedicated workspace, fast Wi-Fi a well equipped kitchenette and a seasonal stock tank pool. Enjoy private walking trails on a scenic farm yet you’re only 45 minutes from Notre Dame, Shipshewana, and Lake, Michigan beaches. A charming and peaceful getaway awaits.