Holiday rentals with a pool in Grand Beach

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Top-rated rentals with a pool in Grand Beach

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

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Top guest favourite
An outdoor seating area features a cushioned sectional sofa and a wooden coffee table, overlooking a heated in-ground pool. Lounge chairs are positioned nearby, surrounded by trees, with a view of Lake Michigan in the background.
Guest suite in Gary
4.98 out of 5 average rating, 115 reviews

Beachfront- Lake Michigan-Hot Tub-Heated Pool

Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

Superhost
The exterior of the cottage is depicted, featuring a single-story structure surrounded by lush greenery. A paved driveway leads to the front entrance, while tall trees provide shade. The house showcases a combination of stone and siding, blending harmoniously with the natural setting.
Home in Grand Beach
4.67 out of 5 average rating, 3 reviews

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.

Guest favourite
A private cottage is surrounded by lush greenery and features a wooden deck adorned with several blue planters. Steps lead up to the entrance, which is framed by large windows allowing natural light to fill the interior.
Guest house in Valparaiso
4.95 out of 5 average rating, 218 reviews

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.

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 Sawyer
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 favourite
The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.
Home in Michigan City
4.96 out of 5 average rating, 186 reviews

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.

Guest favourite
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.
Serviced 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 favourite
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, 231 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 favourite
Guest house in Cassopolis
4.97 out of 5 average rating, 181 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 favourite
The exterior of Lagunitas Coach House is shown, featuring a screened-in porch with two red chairs. Lush greenery and flowers surround the entrance, while a small table rests beside the chairs. A clear blue sky provides a bright backdrop.
Guest house in Michigan City
4.86 out of 5 average rating, 163 reviews

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.

Top guest favourite
Home in New Buffalo
4.95 out of 5 average rating, 113 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) .

Guest favourite
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.

Superhost
Home in Three Oaks
4.87 out of 5 average rating, 139 reviews

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.

Popular amenities for Grand Beach rentals with a pool

Quick stats about holiday rentals with a pool in Grand Beach

  • Total holiday rentals

    Explore 40 holiday rentals in Grand Beach

  • Nightly prices starting at

    Grand Beach holiday rentals start at $164 SGD per night before taxes and fees

  • Verified guest reviews

    Over 450 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Grand Beach holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Grand Beach rentals

  • 4.8 Average rating

    Grand Beach stays are highly rated by guests – averaging 4.8 out of 5!