
Vacation rentals with a pool in New Buffalo
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in New Buffalo
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!

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 .

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.

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 New Buffalo rentals with a pool
House rentals with a pool

Fall Fun in MI! Heated Pool, Hot Tub, Game Room

Fall Fun | Quiet Area | Huge Fenced Yard

Updated 3 bdrm house w/ pool near beach & country

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

24 Acre Secluded Retreat Heated Pool Hot Tub Pond

Modern Farmhouse - Walk to Downtown, beach & pool!

The Keystone Ranch…The only house on the block!

Lake Michigan Beach Cottage + Pool + Games
Condo rentals with a pool

Union Pier Condo with Association Heated Pool.

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

Amazing Beach Condo with pool and great sunsets!

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

Cozy Guest House with Pool near National Park

Charming little piece of heaven with Indoor pool

Marina Sunset: Savor Fall Flavors in Saint Joseph

Buchanan Pool House 2 King Beds 25 min to ND

Beachwalk’s Cozy Cottage - Farmhouse decor

Fabulous designer owned home w/ heated pool & spa!

5BR Beachwalk Gem | Pool Beach Lake Michigan View

Family Tides at Harbor Shores
Quick stats about vacation rentals with a pool in New Buffalo
Total vacation rentals
Explore 60 vacation rentals in New Buffalo
Nightly prices starting at
New Buffalo vacation rentals start at $154 CAD per night before taxes and fees
Verified guest reviews
Over 1,800 verified reviews to help you choose
Family-friendly vacation rentals
60 properties offer extra space and kid-friendly amenities
Pet-friendly vacation rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
60 of New Buffalo vacation rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across New Buffalo rentals
4.9 Average rating
New Buffalo stays are highly rated by guests—averaging 4.9 out of 5!
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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
- Lincoln Park Zoo
- Museum of Science and Industry
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Silver Beach Carousel
- Potato Creek State Park
- Tippecanoe River State Park
- DuSable Museum of African American History
- Deep River Waterpark