Holiday rentals with a pool in Douglas

4.96 out of 5 average rating, 130 reviews

An aerial view showcases a spacious backyard with a fenced, in-ground pool surrounded by lounge chairs. A patio area with outdoor seating is visible next to the house, which is set amidst green grass and trees. The nearby road and horse ranch add to the serene landscape.

Home in Holland

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

4.97 out of 5 average rating, 228 reviews

A modern ranch-style home is surrounded by lush greenery and manicured landscaping. The exterior features a combination of grey siding and a welcoming front porch. A paved driveway leads to the entrance, framed by trees and shrubs, creating a serene wooded environment.

Home in Fennville

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.

4.9 out of 5 average rating, 134 reviews

A comfortable living area is displayed with a light-colored sofa, two matching armchairs, and a round coffee table, all set on polished hardwood flooring. Natural light enters through the windows, illuminating decorative elements such as cushions and a wall mirror.

Condo in Saugatuck

Robyn's Nest Riverside-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, wifi & SEASONAL access to the Ship n Shore Hotel Pool &hot tub (May-Sept)

4.94 out of 5 average rating, 116 reviews

A charming cabin features a wooden exterior with a steeply pitched roof and multiple gabled sections. Lush greenery surrounds the structure, and a welcoming porch is adorned with a wooden railing. Large windows allow for ample natural light, contributing to the inviting atmosphere.

Cabin in Saugatuck

Luxury Cabin Retreat for Families or a Get Away

This cabin is perfect in every way. Whether a romantic hideaway for a weekend getaway, a family vacation with the kids, or with a group of friends; you will be delighted with this fantastic cabin. You'll find a clean, cozy, warm and down to earth place - with the little luxuries and amenities that make your vacation complete, memorable and fun! From the pool to the fire pit to the cozy back porch, the cabin has everything you will need to feel comfortable and pampered during your stay with us.

An enclosed indoor pool area features a large, clear swimming pool surrounded by spacious tile flooring. Illuminated by natural light from the ceiling, several lounge chairs are positioned at the poolside, providing a relaxing atmosphere for guests.

4.97 out of 5 average rating, 104 reviews

The Northern Anchor: Your Perfect Getaway!

The new enclosed subdivision pool & hot tub are now open! Enjoy our beautiful vacation house. 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.

4.92 out of 5 average rating, 168 reviews

An outdoor heated swimming pool is surrounded by a secure fence, featuring multiple turquoise umbrellas and lounge chairs. Lush green lawns and trees provide a scenic backdrop, enhancing the tranquil atmosphere. The pool area is well-lit by the sun, inviting relaxation.

Home in Fennville

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.

4.93 out of 5 average rating, 54 reviews

The open-layout living area features a cozy sofa facing a gas fireplace, with two green armchairs positioned nearby. Large windows allow natural light to fill the space. A colorful wall art piece adds a touch of design, complemented by a coffee table with magazines.

Condo in Douglas

Northern Lights 2 Bed 2 Bath With Pool

Welcome to Pure Michigan! Discover the charm of Saugatuck/Douglas, named one of America's best small towns. Dive into our shared pool (open Memorial Day to Labor Day) and unwind by the gas fire pits. Explore the finest Great Lakes beaches nearby. Indulge in the open-layout living space with a fully equipped kitchen, gas fireplace, and SmartTV. Grill and relax on your private patio or enjoy outdoor games in the green space. Experience the perfect blend of relaxation in Saugatuck and Douglas!

4.97 out of 5 average rating, 154 reviews

Home in West Olive

Book New Years!- Mini Resort Indoor Pool&Sauna

Stay for Christmas, New Year’s or Spring break Current availability 12/16-26 Christmas! 12/31-1/5 New Years! *NO PARTIES&no persons outside of your originally contracted group may visit the property during your stay.* This property is a perfect getaway situated between Holland, Grand Haven & Grand Rapids right on Lakeshore Dr. Our home sits up on a hill overlooking a beautiful 6 acre pond. You will feel as though you are at your own personal resort w/private heated indoor pool & sauna!

4.97 out of 5 average rating, 233 reviews

A spacious living area features a brown leather sofa adorned with colorful pillows. A wooden coffee table is placed in front. A mounted television is positioned above a cozy gas fireplace, complemented by blue walls and natural light filtering through white shutters. A small dining area is visible in the background.

Condo in Douglas

Cozy condo with fireplace perfect for fall fun.

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.

The exterior of a two-story gray and green house is showcased, featuring a stone-accented garage and white-trimmed windows. Lush shrubs line the entrance, and a gravel driveway leads to the garage, set against a backdrop of greenery and a clear blue sky.

5 out of 5 average rating, 226 reviews

Driftwood Shores-Thanksgiving in South Haven!

South Haven is a great place for a Fall or Winter getaway! 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. The Resorts Indoor/Outdoor Pool with retractable roof and outdoor hot tub is open year around from 7 AM to 10 PM. It is included with your stay.

4.95 out of 5 average rating, 288 reviews

The exterior of a blue and white two-story guest house is featured, showcasing large windows and a covered outdoor bar area. A paved patio area can be seen in the foreground, bordered by landscaping with rocks and plants, with a black fence enclosing the outdoor space.

Guesthouse in Zeeland

Honey Bee Ridge Guest House

Our Guest House is located on a quiet country road 15 minutes from beautiful downtown Holland and 20 minutes from beaches, downtown Grand Rapids and Saugatuck. The property sits on 5 acres with the owners home next to the Private Guesthouse. You'll have access to the pool, your own patio with comfortable seating, and a wood fire pit. A 600 acre park with paved running/biking/cross country ski and mountain biking trails is located across the street.

4.93 out of 5 average rating, 135 reviews

A rustic cabin is embraced by lush greenery, featuring warm wooden siding and a welcoming porch. Several large windows allow natural light to illuminate the interior. Landscaping with a variety of bushes and stones enhances the inviting outdoor setting.

Cabin in Saugatuck

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.

Popular amenities for Douglas rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 3 reviews

Home in Saugatuck

The House Secret of Saugatuck Sts 4B/3B Sleeps 14

4.94 out of 5 average rating, 123 reviews

A cozy living room is featured, showcasing two sofas with complementary cushions and a coffee table at the center. Natural light filters through sheer curtains, illuminating the space. A wall-mounted television is positioned near a window with a decorative tree artwork nearby.

Home in Caledonia

GRPoolcation : Work + Play + Stay (GR-Caledonia)

A secluded in-ground pool is surrounded by lush greenery and landscaped gardens. Several lounge chairs are arranged near the pool, which reflects the sky above. Flowering plants and shrubs frame the scene, creating a peaceful outdoor retreat.

4.83 out of 5 average rating, 185 reviews

Experience Nature-Charming Cottage

4.91 out of 5 average rating, 11 reviews

The exterior of a charming two-story farmhouse is surrounded by vibrant autumn foliage. A gravel driveway leads to the entrance, flanked by colorful landscaping. The house features a mix of dark siding and white trim, complemented by a welcoming front porch adorned with seasonal decorations.

Home in Saugatuck

Allegan Gardens

4.95 out of 5 average rating, 20 reviews

A seasonal above-ground pool is surrounded by a wooden deck, reflecting clear blue skies and greenery. Sunlight enhances the inviting appearance of the pool, which is situated in a spacious backyard, bordered by trees and a nearby house.

Home in Holland

1 Happy Acre

The modern home features a two-story facade with a combination of wood and stone accents. Large front windows allow natural light to illuminate the entryway, while a cozy outdoor seating area with white chairs invites relaxation.

5 out of 5 average rating, 76 reviews

Idlewood Cottage, 5BR Home Beaches, Pool & Hot Tub

A warm living area features a stone fireplace beneath a large television displaying a scenic image. Comfortable leather and accent chairs are arranged around a coffee table. Natural light enters through the windows, highlighting the wood flooring and inviting decor.

4.97 out of 5 average rating, 76 reviews

Marina Resort/2 Spacious Living Room/game RM Bar/

4.79 out of 5 average rating, 52 reviews

A spacious outdoor deck surrounds a refreshing pool, featuring reclining lounge chairs and a grill for alfresco cooking. A distinct lighthouse structure stands by the pool, enhancing the charming outdoor ambiance. This inviting area offers ample space for relaxation and gatherings.

Home in Coloma

SouthwestMi Paradise.

Condo rentals with a pool

4.56 out of 5 average rating, 25 reviews

The exterior of the spacious condo is shown, surrounded by lush greenery and mature trees. A patio area with outdoor seating is visible, and the structure's multiple levels reveal balconies overlooking the green lawn, inviting relaxation and enjoyment of nature.

Condo in Saugatuck

Amazing Bayview: Pool, Views, Downtown, Balcony

Love the Sun in MI

5 out of 5 average rating, 23 reviews

Holiday Hill Apartment 701

5 out of 5 average rating, 20 reviews

An indoor swimming pool is framed by large windows allowing natural light to fill the space. Comfortable chairs are positioned around the pool area. A shallow section with stairs is visible, alongside a section designated for lounging. The ambiance is relaxed and welcoming.

Condo in South Haven

Lake Effect Loft +Beach+Downtown+Pool+Hot tub

5 out of 5 average rating, 15 reviews

Condo in Saugatuck

Waterfront condo -pool-beach-bike-hike-shop-chill

5 out of 5 average rating, 24 reviews

Condo in South Haven

South Haven North Shore condo

4.97 out of 5 average rating, 35 reviews

A spacious deck is shown, featuring a wooden table with an umbrella and string lights illuminating the area. The view of the ocean is visible in the background, with a sunset casting soft colors in the sky. The side of the building is also visible, with multiple windows.

Condo in Coloma

Amazing Beach Condo with pool and great sunsets!

5 out of 5 average rating, 12 reviews

An indoor heated pool is enclosed by large glass windows that allow natural light to fill the space. Comfortable lounge chairs are arranged nearby, alongside a pool ladder leading into the clear blue water. The brick walls contribute to a modern and inviting ambiance.

Condo in South Haven

Schoolhouse Suite: Indoor assoc. pool, hot tub!

Other holiday rentals with a pool

4.92 out of 5 average rating, 24 reviews

Steps lead down through lush greenery to a sandy beach beside Lake Michigan. The calm blue water stretches into the horizon, while the clear sky creates a bright and open atmosphere. The wooden steps provide easy access to the beach area.

Apartment in South Haven

North Shore Hideaway

4.96 out of 5 average rating, 48 reviews

A spacious heated pool is surrounded by neatly arranged lounge chairs and green shrubs. The sun shines brightly in a clear blue sky, and nearby trees provide a sense of privacy. A light blue canopy is positioned over one section of the pool area.

Apartment in Douglas

Douglas/Saugatuck Duplex Come See The Fall Colors!

4.96 out of 5 average rating, 71 reviews

An open-concept living space features large windows with natural light illuminating the room. A spacious kitchen with dark wood cabinetry is visible in the background, complemented by a long dining table. A comfortable sofa with decorative pillows faces the seating area, promoting relaxation.

Apartment in South Haven

Old School Condo/Loft in South Haven

Campervan/RV in South Haven

The spacious fifth wheel RV is parked on a paved lot, with an extended awning providing shade. Several outdoor seating chairs and a picnic table are positioned nearby. A black and white patterned rug enhances the outdoor space, while green grass surrounds the unit under a clear blue sky.

4.97 out of 5 average rating, 29 reviews

Luxury Camping/Group or Family/*no site fees*

Townhouse in Saint Joseph

A spacious balcony features a small table and chairs, overlooking a serene marina. The sun shines brightly on the water, reflecting off the surface, while the surrounding docks and distant buildings create a tranquil atmosphere.

5 out of 5 average rating, 9 reviews

Marina Sunset: Savor Fall Flavors in Saint Joseph

4.95 out of 5 average rating, 63 reviews

A collage of images showcases a cozy living space with a gray sofa and natural wood accents. The dining area features a circular table set with tableware. The bedroom includes a king bed adorned with soft bedding. Kitchen amenities are highlighted in soothing colors.

Apartment in South Haven

Downtown Loft: Indoor Pool, Hot Tub, Gym, Theater

4.98 out of 5 average rating, 59 reviews

The modern farmhouse is showcased with crisp white siding against a backdrop of green trees. Features include a metal roof, large windows, and a porch with outdoor seating. A shaded area with a screened porch is visible, enhancing the inviting exterior space.

Cottage in South Haven

Cheerful Cottage, Walk to beach, Pool coming 2026