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

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Top-rated rentals with a pool in Shorewood-Tower Hills-Harbert

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost
The cozy living area features a comfortable sofa adorned with blue accent pillows and a light armchair. Large windows provide natural light and a view of the outdoor space, while a marble countertop in the nearby kitchen area adds a modern touch.
Tiny home in Sawyer
4.91 out of 5 average rating, 100 reviews

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!

Superhost
A spacious outdoor area features a hot tub beside a well-maintained pool. Lounge chairs are positioned around the pool, with a covered seating area in the back. A wooden pergola provides shade, while string lights add a touch of ambiance.
Home in Three Oaks
4.85 out of 5 average rating, 100 reviews

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.

Top guest favorite
The charming exterior of the home showcases a vintage orange convertible parked beside a motorbike, set against a lush backdrop of greenery. The gravel path leads to a welcoming entrance surrounded by tall trees and vibrant foliage.
Home in Three Oaks
4.99 out of 5 average rating, 106 reviews

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.

Guest favorite
A cozy living area showcases a stone fireplace with a decorative metal screen, casting a warm glow. Comfortable seating with blue striped cushions is arranged around a wooden coffee table, with a soft rug underfoot. Natural light enters through nearby doors, enhancing the inviting atmosphere.
Apartment in New Buffalo
4.91 out of 5 average rating, 22 reviews

Serene Woodland Apartment Retreat in Grand Beach

This airy space holds warmth in the details — wooden accents, walls the color of pine and sage, the faint smell of a campfire. One queen bed features a cushy Casper mattress topped with plush Sferra linens. The bathroom, complete with Malin+Goetz bath products, keep things fresh. A small but mighty kitchenette is home to your morning coffee thanks to a Moccamaster coffee machine, fridge + microwave. If you must remain connected to the real world, the WiFi and TV are solid.

Top guest favorite
A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.
Cottage in Union Pier
4.97 out of 5 average rating, 230 reviews

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!

Top guest favorite
Guesthouse in Cassopolis
4.97 out of 5 average rating, 180 reviews

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.

Guest favorite
Home in New Buffalo
4.95 out of 5 average rating, 112 reviews

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) .

Top guest favorite
A charming ranch-style house is situated on a spacious green lawn, surrounded by mature trees. The front features a welcoming porch with seating, and a driveway leads to an attached garage on the right. Lush landscaping enhances the tranquil setting.
Home in Bridgman
4.99 out of 5 average rating, 90 reviews

Fall Fun | Quiet Area | Huge Fenced Yard

Enjoy a quiet, peaceful neighborhood while being close to everything. Five minute drive to Warren Dunes, Weko beach, wine bars, breweries, and restaurants. Three bedroom ranch perfect for your family to relax and have fun. Large fenced in backyard with gorgeous in-ground heated pool (June-September), gas grill, solo stove. Close to many wineries, orchards, and local farms. Lovely area for bicycling!

Guest favorite
A fire pit is surrounded by four teal Adirondack chairs, set on a grassy area. A warm fire burns brightly in the center, with two serene ponds visible in the background, framed by trees and inviting outdoor space.
Cabin in Benton Harbor
4.91 out of 5 average rating, 379 reviews

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.

Top guest favorite
Home in Vandalia
4.99 out of 5 average rating, 209 reviews

Couples, Quiet, Skiing Close, Romantic, Farm, Cozy

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.

Guest favorite
A private outdoor area features a hot tub beside a sparkling pool surrounded by lush greenery. Two lounge chairs are positioned under a large umbrella, and a hammock is visible in the background, providing a serene setting for relaxation.
Home in Chikaming Township
4.91 out of 5 average rating, 47 reviews

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.

Guest favorite
The multi-story townhome features a light exterior with spacious balconies on each level. Large windows illuminate the structure, enhancing its architectural details. Staircases lead up to the front entrance, inviting guests into the living space.
Townhouse in New Buffalo
4.94 out of 5 average rating, 108 reviews

Dunescape Beach Retreat, Downtown New Buffalo

Luxury & Location. A spacious beach getaway in the heart of down town New Buffalo and a short walk from the Marina and the beach. Start the day with the view from the rooftop deck before hitting the private Dunescape pool! Just over an hour from Chicago whether by car or train - the train station is just steps from Beach Retreat.

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