Vacation rentals with a pool in Allegan

Driftwood Shores-SH is a great fall getaway!

September and Fall is starting to book! Enjoy a trip to beautiful South Haven along the shores of Lake Michigan. Driftwood Shores is a charming 1,680 sq. ft. home in the Harbor Club Resort. It has everything you need to enjoy a peaceful family vacation, friends getaway, or girls weekend out. NOTE: AirBnb has changed its pricing structure so that now the host pays the 15.5% service fee (instead of the guest.) Your overall cost hasn't changed, but the nightly rate reflects this new payment system.

Vintage Splendor Historic

My place is good for couples, solo adventurers, families (with kids), big groups, Girls night outs, and furry friends - with a pet cleaning fee. Vintage Splendor is a beautiful, charming historic home with all today's amenities. We are located in the Village of Douglas and are on The Historic Home Walking Tour. This large home boasts 3 formal bedrooms, 2-1/2 Bathrooms and a den that serves as a 4th bedroom. This Victorian home sleeps 10 with 6 beds (Two King, Two Queen, & a pull out Trundle.

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 Chain Ferry Nest #2

Enjoy nesting in the heart of downtown Saugatuck with a view of the water, park & Chain Ferry, a designated parking spot, hardwood floors throughout, bedroom w KING bed adjoining full bathroom, 40”smart tv, w/ privacy door to living area, w/ sofa bed, 50” smart tv w/YOUTUBETV streaming access w/600MBPS WiFi service, equipped kitchen w/ cooktop, oven, microwave, full refrigerator, dishwasher, washer, dryer, coffee maker, SEASONAL access to Ship n Shore Hotel waterfront Pool &hot tub (May-Sept)

Lakeshore Woods Escape

Walk to the beach from this stylish, 6 bed, 6.5 bath home. With accommodations for 20, this house has it all for your family vacation, friends getaway, or group retreat. Surrounded by woods with a pool, hot tub, fire pit, lush lawn, game rooms, and an entertainer's kitchen - your vacation home is ready for you! Wineries, farmers markets, and the charming towns of Saugatuck, Douglas, Fennville, and South Haven are a short drive. Close by is a park with restrooms, play area and beach access.

AlleganOrchardsSleeps25Pool,HotTubFireplaceFirepit

ALLEGAN ORCHARDS: Luxe private retreat 5min. to Saugatuck/Douglas/Fennville Lake MI beaches/sand dunes. - Open kitchen - Private heated pool (fees apply - see house rules) - Private outdoor hot tub (open 24/7/365, no fee) - Indoor fireplace - Outdoor fire pit - Screened porch - Game room: Ping pong, billiards, game table, arcade games - Blue tooth sound throughout - Local area: Saugatuck/Douglas ("Art Coast of MI"), award-winning destination: Restos/Antiques/Boat/Hike/Golf/Wineries/Breweries.

Halloween & Christmas Fun- Pool - South Haven, MI

Celebrate the holidays here - Decorated for Halloween in October and Christmas in December! Year round community pool! The ultimate family getaway! Perfect for families with kids or for groups/individuals looking for a fun get away. Close to everything: beaches, downtown shopping, wonderful restaurants, award winning golf courses, pick your own orchards, beautiful wineries and much more. Visit us year round - from snowy woods to sandy beaches - the Northern Anchor has something for everyone.

Cheerful Cottage, Walk to beach, Private Pool

You will love our Airbnb with its light, airy design and easy access to beautiful Lake Michigan. Drink your morning coffee on the wide, covered front porch or on the screened -in back porch. Enjoy a splash in the in-ground, heated, private pool or walk to a wide sandy beach. Play pickleball or ping-pong. In the evenings, grill out on the gas grill and enjoy dinner under the pergola. Take an evening stroll to the beach for the glorious sunsets and then make s'mores by the campfire!

Heated Pool Until 10/31 | Pickleball | Theater Rm

The ultimate midpoint landing for premium lakeshore group takeovers. Located exactly ten minutes from downtown Holland and Saugatuck, this luxury estate captures total privacy with immediate access to pristine coastal hubs. Engineered around elite amenity sequencing, the property features a private pickleball court, heated pool, custom hot tub, and fire pit. Indoors, a premium theater, game room, and chef's kitchen deliver unmatched utility. Reserve remaining peak summer dates.

Fairview | Luxe Pool Paradise!

Step into timeless charm at this designer-owned, beautifully restored 1857 gem, reimagined through the decades. Where old-world character meets modern comfort, every detail - from original architecture to curated art - tells a story. Antiques, vintage finds, and warm interiors invite you to linger. Wake to sunlit mornings, unwind in luxurious rooms, and embrace the calm of a slower pace. Fairview is more than a stay—it’s a soulful retreat that feels like home.

The Garden House Cottage at Redbud Farm

It's summer at Redbud Farm! The Garden House Cottage is a beautifully remodeled old farm barn. Modern boho farmhouse style. This place has charm galore. You'll love the peace and quiet of the country and the gardens are professionally landscaped and maintained. Enjoy the views of the English potager style garden right out the window while relaxing on the queen bed. Traveling with friends/family? Check out my other listing The Granary at Redbud Farm.

Christine's Cottage | Heated Pool Through Sept!

Soak up the last days of summer in Saugatuck! September brings warm days, cooler evenings and fewer crowds—and our heated pool remains open for it all. Christine’s Cottage is a family-friendly summertime oasis just minutes from downtown Saugatuck. The spectacular backyard is made for making memories—swim in the heated pool, unwind in the hot tub, enjoy grilled meals al fresco on the expansive patio, and end perfect days roasting s’mores under the stars.