Vacation rentals with a pool in New Buffalo

Cabin with POOL in family resort!

Nestled within a gated 67-acre resort and just minutes from the shores of Lake Michigan, this charming cabin offers a peaceful retreat ideal for couples, families, or solo travelers, blending rustic décor with modern comforts. Guests can spend their days exploring nearby nature trails, lounging by the pool, paddling across the lake, or unwinding on the porch. The perfect vacation for exploring nearby orchards and countryside, catching live music or theater, or just slowing down and recharging!

Modern Farmhouse - Walk to Downtown, beach & pool!

Newer construction and beautifully decorated w/ Magnolia Farms vibe! Just 2.5 blocks from downtown New Buffalo, 10 min walk to the beach, nearly 2,700 sq ft, situated at the end of a private lane. 4 BR and 3.5 baths on 3 floors with 2 separate living areas, a screened-in patio & covered front porch. Pool table, 2 large TVs w/streaming in separate living areas. Heated community pool for residents & guests, bikes, gas grill and much more! Note: Reservation Agreement to be signed post-booking

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

Play @ The Hideaway - hot tub, sauna, gymnasium

Accommodating up to 22 guests, this expansive 5,891 sqft property is set on 22.6 acres, creating a private oasis complete with a pool, hot tub, sauna, and gymnasium. The residence features a Great Room, fireplace, fire pit, and a private trail, making it an ideal setting for relaxation and recreation. With 3 king-size beds, 4 queen-size beds, and 2 bunk beds with trundles, comfortably catering to the needs of large groups. This venue offers enjoyable experiences for guests of all ages.

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.

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

SUMMER IS BOOKING FAST at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. ONE WEEK RENTALS ONLY DURING SUMMER, FRIDAY CHECK IN. 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.

NB Getaway with HotTub, Pool & 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.

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!

James Dēne 11: Sunset Lake Views and Indoor Pool!

Welcome to The James Dēne 11, your ultimate New Buffalo retreat! This stylish three-story home features two king en-suites with private decks, a cozy fireplace, and a rooftop deck with stunning Lake Michigan sunset views. Relax in the large backyard with a fire pit or enjoy the clubhouse with an indoor pool and hot tub. Perfect for families and friends, this property offers comfort, charm, and space to gather. Book your stay today and experience the best in vacation living!

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

Waterfront property with a private hot tub, pool, and tennis court, making it an ideal destination for those seeking both relaxation and recreation. Visit beautiful Southwest Michigan and stay at the St. Joe Overlook. Take a swim in the pool, unwind in the hot tub, take the kayaks out for a river cruise, or sit by the fire. Enjoy this stunning location and top-notch amenities. A trip to the St Joe Overlook is the perfect place to gather & reconnect. Maximum Guest Count 16.

Marina's Edge

Stay in the heart of downtown New Buffalo at Marina’s Edge, a three-story townhouse directly across from the marina and just steps from Stray Dog, shops, dining, and Lake Michigan. Enjoy open-concept living, three comfortable bedrooms, multiple full baths, garage parking, and front porch and balcony views of the harbor. Guests also have access to a heated association pool in summer. Walk everywhere, soak up the energy, and experience Harbor Country at its most vibrant.

New buffalo Farmstead main home pool hot tub

5 bedroom 2 bath 2200 sq ft modern farmstead , 2 minutes to new buffalo and beach and all its offerings , 18x36 new heated shared pool open 5/20 to 9/20 and hot tub. Property on 3 acres with plenty of room for kids to play , 26 apple trees and woods , ride host bikes to new buffalo .. Best of both worlds in country , close to town .There’s 2 new homes on 3 acre property, this home and 1 guest home ( rented separately) .