Vacation 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
The exterior of the cottage features vibrant blue siding and a covered porch with white railings. Lush greenery and landscaped beds surround the entrance, creating a serene and welcoming façade. A pathway leads to the front door, inviting guests into the home.
Home in New Buffalo
5 out of 5 average rating, 201 reviews

Designer Cottage - walking distance to downtown

Dream cottage getaway just over an hour from downtown Chicago. Walking distance from the beach, restaurants and all of downtown New Buffalo. Close to the casino, wineries and breweries. Whether driving in or taking the train, The Bradford is a relaxing yet sophisticated getaway. Eat, drink, and enjoy the beach, the pool, the shops and incredible summer sunsets, all within walking distance! Please note pool/bathhouse open late May - September and is shared with our association.Permit C22-0051

Superhost
A modern kitchen features light cabinetry and stainless steel appliances. A large island with green bar stools provides ample seating. Pendant lights hang above the island, enhancing the spacious feel. Windows allow natural light to fill the room, creating a bright cooking environment.
Home in Grand Beach
5 out of 5 average rating, 5 reviews

The Glenwood/ 4 bdrm 2.5 ba/ heated pool/fire pit

The Glenwood is a gorgeous 4 bdrm 2.5 ba home, situated in the idyllic village of Grand Beach. This home offers an open concept with a layout perfectly suited for family gatherings. Heated pool and fire pit. Just 1.5 blks to the beach and 2 blks to the park/playground, golf course, tennis, pickeball and basketball courts. The Glenwood is also just a short drive to other nearby activities, restaurants, wineries, breweries, antiques and plenty of shopping. *Minimum age requirement is 28 years.

Superhost
An aerial view captures the inviting pool area surrounded by lush greenery. The sparkling blue pool is framed by several lounge chairs, with a shaded patio leading to a well-maintained RV parked near the entrance. Colorful landscaping adds to the serene outdoor setting.
Camper/RV in Porter
4.82 out of 5 average rating, 743 reviews

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Heated pool open until mid October! Hot tub open all year! Fully equipped RV sleeps 5, has bathroom w/shower, stove, microwave, TV, heat & A/C, & running water all year. Located on the bike trail & only minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hike in the Indiana Dunes National Park along the Little Calumet River & the historic Bailley homestead, only 1 block from the RV. Enjoy our large pool, hot tub, grill, campfire, & playground too. Schedule your visit today!

Guest favourite
A stone pathway leads through lush greenery and colorful flowerbeds toward a light-filled, glass-fronted structure. Towering trees create a natural canopy, enhancing the serene atmosphere of the garden setting.
Home in Three Oaks
4.88 out of 5 average rating, 135 reviews

Harbor Country Charm w Heated Pool Open Til 10/12!

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closes October 10, 2024 through Memorial Day 2025 After a day of exploring the waters of Lake Michigan, Warren Dunes, or nearby wineries, find your sanctuary at Mae's Place. Recharge by soaking in the inviting hot tub, sizzle up a delicious meal on the grill or in the kitchen and end the evening roasting marshmallows around the fire pit or watching an outdoor movie on the pool deck.

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, 183 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.

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
4.96 out of 5 average rating, 224 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!

Guest favourite
A spacious green house features a traditional design with multiple windows on the upper level, bordered by well-maintained landscaping. A large driveway extends in front, accommodating parking for several vehicles, leading to a three-car garage with white doors.
Home in Union Pier
4.85 out of 5 average rating, 194 reviews

New Buffalo / Union Pier Pool Hot tub 6 Bedroom

Relax with the whole family at this peaceful home with Classic European style meets Lake Michigan! This astonishing turnkey home is the perfect escape from life in the busy city. The home is ideal for entertaining Famliy . 5 bed , 4 bath , hot tub and gas grille and( pool opens June 6) close to union pier beaches and wine country . Property is nestled in a quaint country road location 1/2 mile off re arrow highway. Room for 10 cars,blue stone patios,ping pong table .

Superhost
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.
Guesthouse in Michigan City
4.86 out of 5 average rating, 161 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.

Guest favourite
A sunlit living area features large windows that allow ample natural light, showcasing a cozy gray sofa and a round white coffee table on a woven rug. A wall-mounted TV and a small blue armchair enhance the space, while wooden paneling adds warmth.
Apartment in New Buffalo
5 out of 5 average rating, 9 reviews

Woodsy Lake Michigan Getaway: 3-BR, 2-BA

Your childhood dreams have come true: this is an escape amongst the trees [but more comfortable and lux than the plywood box you used to imagine]. Three bedrooms (two with king beds + one with a twin over full bunk bed) feature cushy Casper mattresses topped with plush Sferra linens. Two bathrooms, complete with Malin+Goetz bath products, keep things fresh while a queen sleeper sofa provides extra space for slumber.

Superhost
The exterior of a multi-level house is depicted, featuring a combination of siding and stone accents. Large windows are present, along with balconies on the upper levels. A paved driveway leads to a garage, surrounded by greenery and a clear blue sky.
Home in Michigan City
4.92 out of 5 average rating, 115 reviews

Beautiful home with Beach views in Beachwalk

Enjoy the open concept family room/dining area, flat screen TV, fireplace, and a farmhouse table that seats 12. You can also enjoy the sunset from the top floor "birds nest" with views of the Chicago skyline. The lower level is perfect for kids to watch TV and play games and is equipped with bunks that sleep up to 7 people. A Staircase leads to a private walkway for access to Lake Michigan.

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, 370 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.

Guest favourite
Home in New Buffalo
5 out of 5 average rating, 18 reviews

Lake House Retreat

Unwind with family and friends as you sit and relax in the beautifully designed vacation house that’s perfect for all family and friends’ gatherings. This specious 4-bedroom Vacation House with a charming set up, fully furnished basement and private back yard with heated pool and hot tub, offers a perfect getaway for families or groups looking to unwind in nature or indoors.

Popular amenities for Grand Beach rentals with a pool

Quick stats about vacation rentals with a pool in Grand Beach

  • Total rentals

    40 properties

  • Total number of reviews

    470 reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi