
Vacation rentals with a pool in Grand Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Grand Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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

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.

'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!

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.

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.

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 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 .

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.

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.

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.

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.

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
House rentals with a pool

Walk to Beach & Downtown | Pool Access

6 BR Home w/ Pool, Theatre, Walk to ND Restaurants

Steps from Pool w/ Private Hot Tub in Gorgeous Woo

Updated 3 bdrm house w/ pool near beach & country

Private! Warren Woods Pool Retreat

5BR Beachwalk Gem | Pool Beach Lake Michigan View

Lake Michigan Beach Cottage + Pool + Games

Cabin w/heated pool, near beach
Condo rentals with a pool

Union Pier Condo with Association Heated Pool.

New Buffalo Condo Indoor & Outdoor Pool!

(2026 OPEN!) Union Pier Condo With Heated Pool.

Fall 2 nt min Perfect Location Condo Pools Walk to

New Buffalo Condo with Association Pool and Beach!

Nightingale Dunes - Modern beach town retreat

Sunset Pointe Chalet #31: Beach+ Pool + Games

Sunset Pointe Chalet #32: Beach + Pool+ Sports
Other vacation rentals with a pool

Luxe by the Lake | Pool Access | Near Downtown and

Hot tub open year round and pvt association beach!

Modern Farmhouse - Walk to Downtown, beach & pool!

Buchanan Pool House 2 King Beds 25 min to ND

Beachwalk’s Cozy Cottage - Farmhouse decor

Fabulous designer owned home w/ heated pool & spa!

Enchanting Pool House (2.2 miles from Notre Dame)

Union Pier, 3 BR+loft, hot tub, community 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
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Warren Dunes State Park
- Guaranteed Rate Field
- Oak Street Beach
- University of Notre Dame
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Museum of Science and Industry
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Silver Beach Carousel
- The 606
- Potato Creek State Park
- Tippecanoe River State Park