Vacation rentals with a pool in Michigan

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

Family · Location · Biking

Beachfront- Lake Michigan-Hot Tub-Heated Pool

Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

Location · Family · View

Hilltop Cove- Beautiful 2 bed/ 2 bath in Beachwalk

Welcome to Hilltop Cove! Your perfect getaway at our stunning 2-bedroom, 2 full bathroom cottage in the desirable Beachwalk resort community. Nestled just a short walk or golf cart ride away from the incredible amenities this vibrant community has to offer such as a pool, lake and park. Our property promises a relaxing and fun-filled stay for all guests. Book your stay at our Beachwalk spot and experience the ultimate in comfort, convenience, and coastal charm. We look forward to hosting you!

Family · Location · Decor

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 **

Family · Location · Indoor spaces

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)!

Location · Family · Backyard

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.

Value · Family · Hot tub

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.

Family · Value · Walkability

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!

Family · Location · Bathroom

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.

Family · Location · Pool

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 optional . 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 after payment of grounds fees.

Family · Value · View

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) .

Value · Family · Layout

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.

Family · Location · Check-in