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

Anchors Away - Sawyer, MI

Welcome to our home! We are so excited to get to share our home with you! Our family-friendly has a cozy living room, fireplace and a full kitchen! On site is a heated pool, laundry mat, and it’s home to the Beach Bucket the best spot for amazing ice cream, homemade popcorn and fudge! Directly across the street is Warren Dunes State Park. The 3/4 mile walk, drive or bike ride gets you to the beach for a fun filled day! Climb the dunes, lay in the sand, go for a swim, relax-you’re on vacation!

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.

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

NOW BOOKING SUMMER 2026 at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. ONE WEEK RENTALS ONLY DURING SUMMER, FRIDAY CHECK IN. This designer-owned haven offers both deep seclusion + an open-format layout that invites connection, healing + 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.

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.

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.

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 and hot tub. Property on 6 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 2 new homes on 6 acre property, this home and 1 guest home ( rented separately) .

Just Updated in Lakeside | Pool + Hot Tub + Porch!

Enjoy a newly updated cottage with unique finishes, an enormous screened porch, and a private pool and hot tub. Located just down the street from central Lakeside in Harbor Country, Michigan. A five-minute bike ride to the lake and a 10-minute drive from downtown Sawyer, New Buffalo, and Three Oaks - Lakeside Landing is a relaxing escape in any season to enjoy all that Southwest Michigan has to offer.

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.

Pool & Hot Tub Getaway | Walk to Beach • Wooded

Set in a quiet, wooded setting, this spacious home is ideal for relaxed getaways in every season. In cooler months, the open floor plan and warm interiors make it easy to gather, unwind, and enjoy time together. As the weather warms, forest views, outdoor spaces, and easy access to the pool and nearby beach invite you to slow down, soak up the sunshine, and enjoy a more laid-back pace.

Stay Gold, a Sawyer retreat

Nestled along the breathtaking southern shoreline of Lake Michigan in the charming town of Sawyer, "Stay Gold" is a meticulously designed custom 3-bedroom, 3-bathroom residence crafted for beauty, comfort, and play. Our unique home offers one of a kind amenities such as a hot tub, a private pool, a retro juke box, and a wood burning pizza oven.

Winter Wonderland- Perfect Family Getaway!

Now booking summer weekly rentals for 2026 A peaceful setting with a private swimming pool*, hot tub, fire pit, swing set, and outdoor shower. Wooded surrounding with towering pines. This quiet and serene location is tucked away from it all, but a short drive to all the action. Lots of nature and wildlife to be seen from the backyard.