Holiday 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.

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)

Holiday Hill Cottage 722

The rentals at Holiday Hill sit atop a dune with a commanding view the Kalamazoo River and the city of Saugatuck. The Sundeck and pool area provide front row seats for catching rays and watching boats on the river. The hilltop offers a retreat from the bustle of summer yet is only steps away from the chain ferry to town shops, art galleries, and restaurants, and only a short walk to the beach. Morning coffee on the Sundeck as the town awakens is as magical as evening cocktails under the stars.

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.

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!

Harbor Club Home | YEAR-ROUND Heated Pool, Hot Tub

Welcome to your dream getaway in sought after Harbor Club. This cheerful home, built in 2021, is just a hop, skip, and a splash away from the shared community hot tub and heated pool, which has a retractable roof for year-round fun. Enjoy grilling from the home’s new paver patio. Harbor Club offers golf cart rentals, and a second outdoor pool by the marina along with boat rentals. Dive into comfort in this beautifully furnished space, perfect for creating unforgettable memories. Sleeps 14.

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.

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.

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.

NEW! Two Oaks: Pond-side oasis with pool/hot tub

Brand new secluded home on 5 acres with pool and hot tub. This home boasts 5 bedrooms with 5.5 baths and can sleep 14. The home has too many features to list but a few of them are: Pool, hot tub, fire pit and outdoor kitchen outside. Professional Thermador Kitchen, Sonos sound system, Home theater, full bar, screened in porch, fully fenced rear yard and for our eco conscious friends, solar panels and a geothermal heating and cooling system

Fun condo perfect for summer and fall fun.

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.