Holiday rentals with a pool in Benton Harbor

Pool House near the Indiana Dunes

Open-concept home with a private heated pool May - October. Take a hike, climb a dune & run back down to the lakeshore in downtown Chesterton, a perfect getaway weekend at the Indiana Dunes. Fenced yard, grill, and cozy fire pit. Local markets, festivals, orchards, and farms. Just a few miles from the beach and national park. Saturday's European Market offers a wonderful healthy, fun, entertaining shopping & dining experience for all. Fresh produce, food trucks, mimosa brunches, and candy shops.

Guest favorite! Quiet setting w/heated pool & more

Welcome to our SW Michigan retreat! This freshly updated home in a quiet country setting feels far away from it all but is close to everything Harbor Country has to offer including beaches, dunes, breweries & shopping. With 5 bedrooms & 3.5 baths, there's enough space for your large family or multiple families to relax & enjoy plentiful amenities including heated pool (seasonal), hot tub, trampoline, fire pit, large yard, multiple outdoor dining areas, woods with paved walking path, WiFi & more!

Luxury 5BR Pool-Hot Tub Retreat

Unforgettable Memories Await at Luxurious 5-Bedroom Retreat. Escape to tranquility in our spacious 5-bedroom, 3-bathroom home, just 3 blocks from downtown Douglas and 5 min drive to Saugatuck. Comfortably accommodates up to 9 guests with four queen beds and one twin bed. Unwind in our sparkling pool, relax in the soothing hot tub, or gather around the fire pit for an evening of laughter and stargazing. The house is a perfect haven for families, groups of friends, or anyone seeking a retreat.

The Splash Pad- a secluded pool/hot tub oasis

The Splash Pad is a perfect getaway for families and groups. Our goal is to bring people together for quality time so we created spaces that everyone will love: the (non heated) pool, hot tub, patio, volleyball net and horse shoes, fire pit, indoor gas fireplace, and a spacious living room with a 55in TV. We hope you explore all the local attractions like: beaches, shops, restaurants, breweries, and hiking trails- all within 4 miles of The Splash Pad! Just added a Level 2 EV charger!! Available

Robyn's Mt.Baldhead Nest #3 WaterView of Mt.Baldy

Located at the heart of downtown Saugatuck, this top floor, king bed, nesting spot with river view of Mt. Baldhead, surrounds you with the best of Saugatuck! Enjoy being steps away from the water, park, rentals, Chain Ferry, Star of Saugatuck, restaurants, bars, galleries and shops! RNR nesters also enjoy included seasonal access (Memorial-Oct/7/2024) to the Ship n Shore Hotel waterfront pool & hot tub! RNR is minutes from Lake Michigan, Oval Beach, outstanding wineries, breweries and orchards!

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

'Pool Barn' w/Games & Hot Tub near Indiana Dunes

The Pool Barn offers a great location & unique experience. 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. pool, hot tub, grill, firepit, playground, & we are on hike/bike trail. Inside is ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 6 beds, couch, & full kitchen. *pool table is currently broken due to guests attempting attempting to move it*

Poolside Oasis - Private Heated Pool + Fun Games

Escape to our stunning 4-bed, 1.5-bath home with a private in-ground pool! Bright living spaces, a fully equipped kitchen, cozy bedrooms, and an amazing heated pool await. Conveniently located near charming Saint Joseph, Michigan, with Lake Michigan's sandy shores and vibrant downtown nearby. Indulge in local cuisine, explore nature trails, then return to the comfort of our inviting home. Your ultimate vacation experience awaits! Book now for an unforgettable getaway!

The Poolside Escape | Hot Tub | Arcade | Ping Pong

Welcome to "The Poolside Escape" brought to you by Book N Gather vacation rentals. Discover a beautifully renovated single-story ranch with a finished basement, just minutes from Southwest Michigan’s best beaches, state parks, and wineries. Perfect for families or friends, The Poolside Escape offers modern amenities, including a private pool, hot tub, and entertainment options, to make your getaway truly unforgettable. Pool open Memorial Day to September 15th