Holiday rentals with a pool in Stevensville

The Oasis Retreat

The Oasis Retreat is a newly remodeled home with a private heated pool & hot tub, just 4 blocks from downtown South Haven & close to Lake Michigan beaches, marina, trails, restaurants, bars & shops. Perfect for families & groups, the private backyard has an outdoor bar, fire pit, gas grill, pizza oven, ping pong, outdoor shower & detached guest unit w/ seasonal bath/shower. Inside: kitchen, laundry, fast WiFi, Roku TVs, heat/AC, sleeper sofa & upstairs loft. Pool: May-Oct Hot tub: Year-round

Family · Value · Condition

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.

Location · Value · Checkout

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)!

Family · Location · Check-in

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.

Family · Location · Amenities

Modern Lake House w/ Private Pool near New Buffalo

A quick 90-min drive from Chicago - This modern, minimalist, airy, newly constructed home nestled in private sand dunes steps away from Lake Michigan beaches, Grand Mere State Park, and all that SW Michigan has to offer! Relax in the hot tub after a day of hiking, touring wineries/breweries, fine dining, or enjoying the beach. Complete with its own private pool, fire pit & hot tub, ‘The Wedge' offers you a unique escape to connect with nature - a perfect getaway with friends & family!

Family · Value · TV

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.

Location · Family · Bathroom

Lake Michigan Beach Cottage + Pool + Games

Escape to our newly remodeled chalet that is steps away from Lake Michigan. With 6 beds, it's the perfect getaway for couples, families, or small groups. Enjoy access to a private and public beach, pools, sports courts, fishing ponds, and playgrounds. Located next to Lincoln Township Park and near Grand Mere State Park plus nearby breweries, wineries, and distilleries. Relax, explore, and create unforgettable memories at this cozy lakeside retreat. Your perfect vacations awaits!

Family · Location · Wi-Fi

Cozy Cabin

The Cozy Cabin is a freshly renovated woodland retreat situated on 150 private acres, ideal for families, couples, or groups of friends. Sleeps up to 6 with 2 bedrooms, 1 bath, a full kitchen, Smart TV, Xbox, Wi-Fi, and board games. Enjoy wooded trails, peaceful ponds, a fire pit, cornhole, a playground, and a seasonal shared pool with paddleboats. Dog-friendly and just a short drive to Lake Michigan beaches, wineries, U-pick farms, and local attractions. Perfect for nature escapes.

Family · Value · Amenities

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!

Value · Family · Accuracy

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 · Checkout

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) .

Family · Value · Access

Studio apartment for two with pool & hot tub!

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.

Location · Family · Getting around