
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

'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!

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.

NB Getaway w/HotTub,Pool,BBQ & Priv Screening Room
Richly designed 6BR/5BA home near New Buffalo Harbor and beaches. Great Room with stone fireplace. Chef’s kitchen with marble-top island. 3-season sunroom. Elegant, comfy furniture. Primary BR with stone fireplace, twin sinks, tile walk-in shower, and jacuzzi. Lower-level Guest BR with fireplace, full BA, game room, and screening room. Second floor features loft space, 3 BRs, 2 BAs, and a Mother-in-Law Suite with kitchen. Smart TVs in 5 BRs. BBQ deck, firepit patio, and hot tub.

Lakeside getaway with Pool/Beach Access, Balcony
This airy space holds warmth in the details — wooden accents, walls the color of pine and sage, the faint smell of a campfire. One bedroom (with a 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. Kitchen includes a Moccamaster coffee machine, fridge, microwave + two burners. Enjoy stargazing on your private porch.

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 .

Wabi Sabi Chic at The Flamingo Ranch in Lakeside
Autumn at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. Equal parts sanctuary and playground, 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.

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

Luxury home with pool.

Beautiful, sunny 4 BR home with pool and hot tub

Fall Fun | Quiet Area | Huge Fenced Yard

Large, Cozy, Theatre, Pool, Walk to ND Restaurants

Modern Farmhouse w/ Pool Near St Joe

Updated 3 bdrm house w/ pool near beach & country

Private! Warren Woods Pool Retreat

Hot Tub | Backyard Oasis | Game Room | |Coffee Bar
Condo rentals with a pool

Union Pier Condo with Association Heated Pool.

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

Fall 2 nt min Perfect Location Condo Pools Walk to

Amazing Beach Condo with pool and great sunsets!

Nightingale Dunes - Modern beach town retreat

New Buffalo Condo with Association Pool and Beach!

Sunset Pointe Chalet #31: Beach+ Pool + Games

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

Luxury Cottage with pool; summer will book fast

Steps from Pool w/ Private Hot Tub in Gorgeous Woo

Marina Sunset: Savor Fall Flavors in Saint Joseph

Luxurious 5BR | Pool | Hot Tub | Deck | Firepit

Buchanan Pool House 2 King Beds 25 min to ND

Family Tides at Harbor Shores

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 vacation rentals
Explore 40 vacation rentals in Grand Beach

Verified guest reviews
Over 470 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of Grand Beach vacation 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!
Destinations to explore
- Chicago Vacation rentals
- Downtown Chicago Vacation rentals
- Northeast Ohio Vacation rentals
- Indianapolis Vacation rentals
- Platteville Vacation rentals
- Detroit Vacation rentals
- St. Louis Vacation rentals
- Southern Indiana Vacation rentals
- Louisville Vacation rentals
- Columbus Vacation rentals
- Cleveland Vacation rentals
- Cincinnati Vacation rentals
- Rentals with lake access Grand Beach
- Rentals with a fireplace Grand Beach
- Rentals with outdoor seating Grand Beach
- Rentals with a firepit Grand Beach
- Cabin rentals Grand Beach
- Family-friendly rentals Grand Beach
- Beachfront rentals Grand Beach
- Rentals with a patio Grand Beach
- Cottage rentals Grand Beach
- Rentals with beach access Grand Beach
- Rentals with a washer and dryer Grand Beach
- Pet-friendly rentals Grand Beach
- House rentals Grand Beach
- Fitness-friendly rentals Grand Beach
- Rentals with a hot tub Grand Beach
- Rentals with pools Berrien County
- Rentals with pools Michigan
- Rentals with pools United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Warren Dunes State Park
- Oak Street Beach
- University of Notre Dame
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Museum of Science and Industry
- Willis Tower
- Washington Park Zoo
- The Beverly Country Club
- Silver Beach Carousel
- Potato Creek State Park
- The 606
- Tippecanoe River State Park