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Harbor Country Poolside

Harbor Country Poolside is a private luxury retreat in Union Pier, just minutes from Lake Michigan’s beaches. This 3-bedroom, 2.5-bath cottage features designer furnishings, plush bedding, and a fully equipped entertainer’s kitchen. Outdoors, enjoy resort-style amenities including a private, heated, saltwater pool, spa hot tub, fire pit, and serene three-season room surrounded by lush trees. Every space has been thoughtfully curated for relaxation and connection. 2026 Pool Dates: 5/7 - 10/11.

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Beautiful home in the heart of Beachwalk, across the street from Lake Kai, pools, basketball & tennis courts and 2 blocks to Lake Michigan. This home is bursting with charm. Front porch runs the width of the house. Dining area opens up to family room with a lovely fireplace. Stunning master bedroom w/walk-in closet and beautiful new bathroom with all the finishes. 3 more bedrooms upstairs, one with full bathroom attached and the other 2 sharing bathroom. 5th bedroom on the lower level.

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.

Sauna | Hot Tub | Heated Pool | Beach Walk

Welcome to Little Arches, a refined Fisher 3 luxury retreat in the private village of Grand Beach. This 6-bed, 4.5-bath home sleeps 12 and blends wellness and comfort just minutes from Lake Michigan. Walk to the beach or unwind at home with a sauna, 8-person hot tub, heated pool (May–Oct, fee applies), and fire pit. Inside: chef’s kitchen, 3-season room, game lounge, and theater-style lower level. A peaceful escape near golf and New Buffalo. Rental Agreement Required After Booking.

Modern 5-Bedroom New Buffalo Lakeside Escape

Escape to this stylish and spacious 5-bedroom house in New Buffalo, ideal for large families or groups. This home is perfectly located just a short stroll (3 blocks) from the vibrant shops and restaurants of downtown New Buffalo and within easy walking distance (6 blocks) of the beautiful beach. Enjoy the quiet of a serene dead-end street in a charming neighborhood, relaxing on the covered front porch or enclosed back porch. Guests have access to the pool within the neighborhood.

Cozy 1BR/1BA Retreat w/ Pool Access + Near 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 king 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.

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!

NEW! 1BR Cottage w/ Pool, Firepit, Walk to Beach

Presenting Townie 1 - The Ivy, part of the unique Townie Cottages collection. This newly built lakeside luxury home was designed exclusively by Kate Marker Interiors (recognized by Architectural Digest and Luxe Home). Located in Union Pier, these exquisite cottages blend rustic charm and modern elegance for an unforgettable stay. Immerse yourself in a meticulously curated interior with high-end finishes and chic furnishings, creating a sophisticated yet homey atmosphere.

Casa Playa - Union Pier Home w/ Pool & Private Spa

This 4 bedroom getaway is located in the heart of Harbor Country and is just a 10 minute walk or 3 minute drive to the best beach in Union Pier! Casa Playa has EVERYTHING a vacation house can offer: an association POOL, a private HOT TUB, high speed internet that accommodates many people working from home, a cozy indoor fireplace, an outdoor fire pit, an outdoor deck & grill, 2 smart Tvs, ALL brand new appliances, and games for the whole family!

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) .

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.