Holiday rentals with a pool in Grand Beach

Private Heated Pool + Fire Pit | Steps to Beach

The Resting Nest is a charming 2 bedroom 2 bath cottage located in beautiful Grand Beach. Just steps from the beach, this cottage is the perfect place to create beautiful memories with family and friends all summer long. Located just two blocks to the playground, golf course, tennis/basketball courts and a short drive to other activities such as restaurants, wineries, breweries and shopping. *You must be at least 27years to book and provide a copy of your driver's license at time of booking.

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 mandatory. 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 . The cottage is sanitized after every rental.

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.

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.

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.

'Pool Barn' w/Games & Hot Tub near Indiana Dunes

Hot tub open all year! Pool will reopen May 1. The Pool Barn is only 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. Outside enjoy our Pool, hot tub, grill, firepit, playground, & we are on the hike/bike trail. Inside is billiards, ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 5 beds, couch, & full kitchen. No cleaning fee. Book today!

Roomy Studio Retreat w/ Kitchen, W/D, Sleeper Sofa

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 while a queen sleeper sofa provides extra space for slumber. A small but mighty kitchenette is home to your morning coffee thanks to a Moccamaster coffee machine, fridge, and microwave.

Lagunitas Coach House in Beachwalk, Lake Michigan

Lagunitas Coach House is a sought after location on the quaint Thomas blvd cul de sac. It is the coach house to Gooch Life. It is the perfect get away spot for a couple or small family wanting to escape to the beautiful beach of Lake Michigan. Lagunitas and Gooch Life share the property but are separate structures. Lagunitas has a private entrance, amenities, and parking. Lagunitas sleeps 6, see pictures for bed configuartion.

Marina Sunset: Spring Break in Style

Located in the beautiful beach town of Saint Joseph, Michigan, this brand new waterfront townhome is located within Harbor Shores Resort. The area's natural beauty can be seen throughout several dunes areas and beaches nestled on the southeast corner of Lake Michigan. Enjoy wineries, award winning breweries, and an abundance of restaurants. There are adventures abound with boating, fishing, hiking, and biking all nearby.