
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.

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

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.

Epic Indoor Pool w/slide & hot tub close to beach
Escape to Vine Vista, a 3+ acre retreat near Lake Michigan beaches, wine & beer tastings & the third coast. Enjoy a large private indoor heated pool (larger than many hotels!) & hot tub. Accommodates groups of up to 25. You can see why it will be featured in the Emmy Award-winning show Staycation as one of the highlights of the area. Unwind in privacy, but close to local attractions. Dining accommodations for family reunions, birthday celebrations, holidays or bachelor/bachelorette parties.

'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 .

Country cottage with hottub for two!
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.

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.

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.
Popular amenities for Grand Beach rentals with a pool
House rentals with a pool

The Poolside Escape | Hot Tub | Arcade | Ping Pong

Modern Farmhouse w/ Pool Near St Joe

Updated 3 bdrm house w/ pool near beach & country

5K SqFt 2 GameRms, ExecGym, Resort Pool, Spa/Sauna

Heated Pool | Kayaks | Hot Tub | Game Rooms |

5BR Beachwalk Gem | Pool Beach Lake Michigan View

NEW Walk to Lake_Pool_Hot Tub_Game Room_EV level 2

James Dēne 11: Sunset Lake Views | Indoor Pool!
Condo rentals with a pool

Union Pier Condo with Association Heated Pool.

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

Idyllic New Buffalo Condo: Walk to Beach & Shops!

Fall 2 nt min Perfect Location Condo Pools Walk to

Amazing Beach Condo with pool and great sunsets!

New Buffalo Condo with Association Pool and Beach!

Nightingale Dunes - Modern beach town retreat

Sunset Pointe Chalet #31: Beach+ Pool + Games
Other vacation rentals with a pool

Rosie’s Cottage close to Warren Dunes (w pool)

Cozy Guest House with Pool near National Park

Steps from Pool w/ Private Hot Tub in Gorgeous Woo

Marina Sunset: Savor Fall Flavors in Saint Joseph

Modern Farmhouse - Walk to Downtown, beach & pool!

A-Frame On Lake Michigan - beach, sports, + pool

Peaceful Lake Michigan Getaway!

Enchanting Pool House (2.2 miles from Notre Dame)
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