Holiday rentals with a pool in New Buffalo

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

4 Bedroom home w/pool in St. Joseph

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

Beachwalk Home on Lake Kia - W/ Cart Rental Option

Our Lakehouse is unique in that it's sits directly on Lake Kai - Beachwalk's beautiful interior Lake. Of the 200+ homes located in "Beach Walk" Resort, less than 20 are on Lake Kai making our home very unique & your vacation memorable. It’s definitely one of the most sought out locations in all of Beachwalk ** Exciting NEW Update for the 2026 Season New Golf Cart Rental Option - reserve after booking ** Minimum 30 years of age to book ** ** Maximum capacity is 8 Adults and 8 Children **

Atomic Acres-POOL, Summer 2026 Awaits!

Atomic Acres is a remodeled, 4 bedroom/3,000 sq ft home in the heart of Harbor Country in Sawyer, MI. This home sits on 5 beautiful acres with a fenced in side yard and open back yard with a wandering creek along its border. The amenities are endless: fire pit, seasonal pool & hot tub, patio, ping pong table, pool table, screen porch and more! An aesthetic nod to the mid century era is felt throughout with pieces curated to appeal to the vintage, and all so close to Warren Dunes (1 mile)!

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.

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!

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.

Lakeside with heated pool & pvt beach access!

LAKESIDE COTTAGE - POOL, HOT TUB & RARE semi-private Lake Michigan access to gorgeous beach shared by just 10 homes, so it’s never crowded! Beach access is a 7-min walk away (no parking). A few 3-4 night stays available this JUNE & JULY! Charming, sun-filled cottage sleeps 8 (3BR + pull-out). Heated 85 degree pool (May 22–Sept 15), hot tub, fire pit, gas fireplace, spacious deck, bluestone patio & grill. 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!

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 10/ 20 and hot tub open year round maintained at 104 f . 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 1 other home on 3 acre property, this home and 1 guest home ( rented separately) .

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

Just a few days left this summer at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. This designer-owned haven offers both deep seclusion + an open-format layout that invites connection to loved ones and nature + 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.