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.

AlleganFields:Sleeps24,Pool,HotTubFireplaceFirepit

Luxe peaceful private retreat, expansive views, yet steps to town - Sleeps 24 - Open kitchen - Private heated pool (fees apply see house rules) - Private outdoor hot tub (open 24/7/365 no fee) - 2 indoor fireplaces - Outdoor FirePit - Game room: PingPong, mini pool table, 14 arcade games (PAC-MAN, etc) - Blue tooth sound system - Local area: Saugatuck/Douglas ("Art Coast of MI"), award-winning destination: restos, antiques, boat, hike, golf, wineries, breweries. Near Lake MI beaches/sand dunes

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)

Renovated Golf Course Home | Private Pool/Hot Tub

Check out those sunset views over Clearbrook Golf Course! Newly renovated single-family home vacation rental across from golf course (and walkable to the Clearbrook Grill Room) with your own HEATED POOL, hot tub and firepit. Talk about convenience for all you golf enthusiasts (and plenty to appease even for those who are not)! Clearbrook Cottage is also only a short distance to downtown Douglas or Saugatuck for dining, shopping, or boating. See why everyone loves this Art Coast of Michigan!

Beach-Themed Game Room & Pool Near Lake Michigan

The Northern Anchor: Year round community pool & hot tub! The ultimate family getaway! Fully furnished with loads of thoughtful details. Perfect for families with kids or for groups/individuals looking for a relaxing 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 Open through Oct | Theater | Fire Pit

Fall pool season is here at Fisher 3’s flagship luxury estate. Heated to 85° through the end of October ($100/day), the pool, hot tub, fire pit, and private 6-acre lake make this the perfect fall getaway. Just a scenic 1.2-mile walk to downtown Saugatuck on walking paths. Fully redesigned in 2026 with 5 bedrooms, luxury theater, immersive game room, chef’s kitchen, and expansive outdoor spaces. Ideal for golf trips, bachelor/bachelorette weekends, or unforgettable family escapes.

Lux Cabin Twin Peaks East • Private Pool & Hot Tub

Escape to a peaceful, woodland retreat with this high-end A-frame cabin in Fennville, Michigan. This 5-bedroom, 3-bath cabin features three floors, two living rooms, an inground pool and fire pit offering the perfect balance of modern luxury and nature. Located just minutes from the vibrant Saugatuck-Douglas area and its welcoming, inclusive community. This is the ultimate destination for groups, families, and friends seeking quality time, adventure and tranquility.

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.

Fun condo with open pool through September!

Beautifully updated vacation condo with association pool perfect for spring summer or fall vacation. Close to Lake Michigan and all of the fun activities Saugatuck-Douglas has to offer. Less than 1 mile to Lake Michigan. Close to Douglas and Oval Beaches. Enjoy a drink on your own front porch. One bedroom one bath with a cozy gas fireplace. Additional sleeping for two on pull out couch in the living room. Close to bike path to downtown.