Holiday rentals with a pool in Berrien County

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.

Anchors Away - Sawyer, MI

Welcome to our home! We are so excited to get to share our home with you! Our family-friendly has a cozy living room, fireplace and a full kitchen! On site is a heated pool, laundry mat, and it’s home to the Beach Bucket the best spot for amazing ice cream, homemade popcorn and fudge! Directly across the street is Warren Dunes State Park. The 3/4 mile walk, drive or bike ride gets you to the beach for a fun filled day! Climb the dunes, lay in the sand, go for a swim, relax-you’re on vacation!

Luxe Family Retreat • Pool & Hot Tub Near Beach

Entirely renovated and outfitted for multiple families, The Nest Lake Michigan is the perfect place for your next escape from the ordinary. Convenient to all the adorable beach towns of SW Michigan, and 90 mins from Chicago. The grounds feature a heated pool, hot tub, unrivaled outdoor kitchen, games, toys, books, and all the luxury amenities you need for the ultimate staycation. Bike 12 minutes to the nearest beach access, or drive 12 mins N to St. Joe's, or 8 mins S to Warren Dunes.

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

NOW BOOKING SUMMER 2026 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.

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.

NEW! 1BR Cottage w/ Pool, Firepit, Walk to Beach

Presenting Townie 1 - The Ivy, part of the unique Townie Cottages collection. This newly built lakeside luxury home was designed exclusively by Kate Marker Interiors (recognized by Architectural Digest and Luxe Home). Located in Union Pier, these exquisite cottages blend rustic charm and modern elegance for an unforgettable stay. Immerse yourself in a meticulously curated interior with high-end finishes and chic furnishings, creating a sophisticated yet homey atmosphere.

Bibi's Retreat- Grand 7 Bedroom Private Escape

Bibi's Retreat-Nestled among 6,000 trees along 15 acres of secluded property. This is the ultimate private getaway. Located in Niles, MI, the home offers 7 true bedrooms with plenty of space for multi-family living. We are within 30 min of 15 wineries and breweries. We are within 20 min of 10+ golf courses and 20 min to Notre Dame. Ladies Retreat, Golf Getaway or Winery Tours, this home is perfect for large groups.

Family Tides at Harbor Shores

The ultimate family retreat awaits at this 3BR townhouse, boasting captivating marina views. Unwind in comfort with two restful king beds for a good night's sleep after family adventures. Explore charming cafes, exciting water sports, golfing, and Silver Beach. Embark on riverside strolls along the paved walkway, let the kids splash in the inviting heated pool, and stay seamlessly connected with fast Wi-Fi.

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 and hot tub. Property on 6 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 6 acre property, this home and 1 guest home ( rented separately) .

Just Updated in Lakeside | Pool + Hot Tub + Porch!

Enjoy a newly updated cottage with unique finishes, an enormous screened porch, and a private pool and hot tub. Located just down the street from central Lakeside in Harbor Country, Michigan. A five-minute bike ride to the lake and a 10-minute drive from downtown Sawyer, New Buffalo, and Three Oaks - Lakeside Landing is a relaxing escape in any season to enjoy all that Southwest Michigan has to offer.

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.