Holiday rentals with a pool in Shorewood-Tower Hills-Harbert

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!

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!

Fabulous designer owned home w/ heated pool & spa!

Fabulous designer owned home with heated pool & spa in the heart of Sawyer--the ultimate Harbor Country getaway. Renovation has been recently completed at this amazing 5 bedrooms, 5 bath home w/ heated pool and year-round spa. Wonderful, spacious residence with multiple living areas, two fireplaces, & fully stocked dream kitchen. Secondary family room in lower level. Newly landscaped yard designed w/ privacy in mind w/ fire pit, dining folly, and fully fenced yard w/multi-level deck. Perfection!

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.

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.

Rosie’s Cottage close to Warren Dunes (w pool)

Welcome to Rosie's Cottage! The cottage has three bedrooms with queen beds, two bathrooms, a fully appointed screened in porch, a lovely fenced deck, an outside eating and lounging area, a full additional kitchen, and fire pit (with seating)! During the summer we have a heated pool. (POOL CLOSED FOR SEASON) And don’t forget the kids' playroom, twin daybeds and pull-out couches in the basement for movie nights with the kids. The cottage is walking distance to the beach and Warren Dunes.

NB Getaway with HotTub, Pool & Priv Screening Room

Richly designed 6BR/5BA home near New Buffalo Harbor and beaches. Great Room with stone fireplace. Chef’s kitchen with marble-top island. 3-season sunroom. Elegant, comfy furniture. Primary BR with stone fireplace, twin sinks, tile walk-in shower, and jacuzzi. Lower-level Guest BR with fireplace, full BA, game room, and screening room. Second floor features loft space, 3 BRs, 2 BAs, and a Mother-in-Law Suite with kitchen. Smart TVs in 5 BRs. BBQ deck, firepit patio, and hot tub.

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is optional . Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area after payment of grounds fees.

Heated Pool + Fire Pit | Near Warren Dunes

Welcome to The Sawyer Retreat! Located in beautiful Sawyer, MI. Nestled on a serene wooded lot, this spacious 3 bedroom 3 bath home offers the perfect blend of comfort, style, and outdoor fun. Just 5 minutes from the beach and Warren Dunes State Park, and a short drive to local wineries, breweries and boutiques that make Harbor Country a favorite destination. Please note the pool is open Memorial Day Weekend through last weekend in September, weather permitting.

Las Moras, 6 Acres, and a Large Pool

Unwind at Las Moras (“The Berries” in Spanish), a peaceful countryside retreat surrounded by nature. Stroll past rows of blueberry bushes, watch deer wander through the front yard, spot wild turkeys in the woods, and see turtles basking by the pond—all from the comfort of your own private escape. Take a dip in the 25×30 heated saltwater pool, relax among flowering shrubs and towering trees, and enjoy the calm of six secluded acres bordered by an open land preserve.

New buffalo Farmstead main home pool hot tub

5 bedroom 2 bath 2200 sq ft modern farmstead , 2 minutes to new buffalo and beach and all its offerings , 18x36 new heated shared pool open 5/20 to 10/ 20 and hot tub open year round maintained at 104 f . Property on 3 acres with plenty of room for kids to play , 26 apple trees and woods , ride host bikes to new buffalo .. Best of both worlds in country , close to town .There’s 1 other home on 3 acre property, this home and 1 guest home ( rented separately) .

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

Just a few days left this summer at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. This designer-owned haven offers both deep seclusion + an open-format layout that invites connection to loved ones and nature + memory-making. Whether you’re gathering with family, reuniting with old friends, or seeking a rejuvenating escape, we deliver an experience that’s as comfortable + stylish as it is energetically charged.