Holiday rentals with a pool in Allegan County

FennWoods - A Modern, Wooded Retreat

Serene, nature-filled escape in Fennville. Vacation or just feel like you’re on vacay while you remote school/work from the woods. Modern 3 bd ranch on 10 tree-covered acres. Minutes from downtown Fennville & easy access to Saugatuck/Douglas & beaches. Above ground heated pool in season, hot tub, fire pit, playset. Two living rooms & open kitchen/dining. When you’re not taking in all the outdoors have to offer, unwind in front of the fireplace. Wifi, TVs with complimentary streaming, & laundry.

Robyn's Chain Ferry Nest #2 Water-Chain Ferry View

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, wifi & SEASONAL access to the Ship n Shore Hotel Pool &hot tub (May-Sept)

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.

Cute condo with pool open through September

Beautifully updated vacation condo with association pool perfect for 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. Relax on your own front porch or walk a few steps to Isabel’s, a wonderful eatery right on site. 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.

Luxury Retreat | Pool | Pickleball | Theater & Gm

✨ Escape to your private retreat near Lake Michigan—just minutes from Holland, Saugatuck & Laketown Beach! Sleeps up to 16 guests and packed with resort-style amenities: 🏖️ Heated pool (5/1–10/30, fee), 🔥 hot tub & firepit, 🎥 theater room, 🕹️ game room, 🥒 pickleball, 🎯 cornhole & a chef’s kitchen perfect for hosting. Whether it’s a family vacation or group getaway, this home delivers space, style & unforgettable vibes. Message us to elevate your stay with concierge services!

7bd|8bt Spa, Pool, GameRm, Sauna

Welcome to Grapes&Vines, a breathtaking modern chalet, nested near famous Modales and Fenn Valley Wineries and Virtue Cider. The house was built and renovated in Nov'24 with a professional designer meticulously crafting every space to make your trip unforgettable. It boasts a movie theater, a professional tiled pickleball court, an in-ground heated salt water pool (open mid Apr-Oct), a game room, a sauna and stunning 7bd|8bth that can comfortably accommodate up to 20 ppl.

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

Heavenly 7 Retreat Luxury Cabin -Kingfisher Cove

Our cozy 3 bedroom, 2.5 bath luxury rustic cabin features all the comforts of home and more. Fully furnished for your comfort with towels, linens and other necessities. This cabin sleeps 8 comfortably. A heated pool and lake access are available from Memorial Day to mid September. Full-size washer & dryer in the cabin for your convenience. For larger groups, ask about availability to also rent one of our affiliated cabins nearby.