Vacation rentals with a pool in Allegan

Summerset Cottage & Suites, King Suite

Welcome to Summerset Cottage & Suites. Kick back and relax in this stylish, newly built properties King guest suite with a private entrance. Located on the edge of the city limits of Douglas overlooking a large meadow with a beautiful saltwater pool, it's strategically located close to Lake Michigan and downtown Douglas. The large 2nd floor King Suite has been thoughtfully designed with a small kitchenette, fireplace and a beautiful light filled sitting area. 15.5% Airbnb rate has been added

Family · Location · Beach

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.

Location · Value · Check-in

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.

Location · Value · Sleep quality

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

Family · Location · Biking

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.

Location · Family · Hospitality

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.

Family · Value · Comfort

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!

Family · Location · Condition

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.

Family · Location · Checkout

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.

Family · Location · Amenities

Luxury Escape • Hot Tub, Game Room, Heated Pool

Chillin Away is tucked between South Haven and Saugatuck. Relax in a heated seasonal pool, or unwind in the year-round hot tub. With 3 king suites, a custom bunk room, a fully stocked chef’s kitchen, arcades, shuffleboard, this retreat is crafted for families and friends seeking comfort, connection, and resort-style amenities in complete privacy. This newly built, professionally designed home offers resort-level amenities rarely found in private rentals near Lake Michigan.

Location · Family · Getting around

Robyn's Top Notch Nest#7

Nestled in the heart of downtown Saugatuck, this top notch nesting location has you perched on the top floor, surrounded by the towns best attractions! Robyn's Nest Riverside is your key to RNR poolside at the Ship n Shore Hotel! Walk across the street to enjoy included access (5/15-9/15) to Saugatuck’s best waterfront pool and hot tub! Enjoy taking in the boat traffic with iconic views of Mt Baldhead, Saugatuck Chain Ferry and the Star of Saugatuck paddle boat

Location · Family · Nearby

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.

Value · Family · Amenities