Holiday rentals with a pool in Kalamazoo

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.

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.

4.97 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.

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)

Welcome to GR Poolcation: Ideal for families & remote working pros! Enjoy a fully equipped office, cozy living room, deck & patio, and an underground pool (pool will be closed from Oct 1st to end of April 30th). Please note that pool heating is available upon request for an additional fee. Embrace togetherness & camaraderie in our entire home. Make meals, memories, & explore nearby attractions. Book now for productive, convenient, and fun stay! Caledonia, MI (Grand Rapids Suburb)

4.97 out of 5 average rating, 126 reviews

An aerial view showcases the spacious outdoor area, featuring a blue tennis court adjacent to a rectangular pool surrounded by lounge chairs. Lush greenery and trees frame the property, while a well-maintained lawn offers additional recreational space.

Villa in Niles

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

Waterfront property with a private hot tub, pool, and tennis court, making it an ideal destination for those seeking both relaxation and recreation. Visit beautiful Southwest Michigan and stay at the St. Joe Overlook. Take a swim in the pool, unwind in the hot tub, take the kayaks out for a river cruise, or sit by the fire. Enjoy this stunning location and top-notch amenities. A trip to the St Joe Overlook is the perfect place to gather & reconnect. Maximum Guest Count 16.

4.91 out of 5 average rating, 309 reviews

A game room features a multi-game table for pool, air hockey, and ping pong, surrounded by comfortable bean bag seating. Bright, geometric lighting enhances the space, while classic arcade machines and a large wall Connect 4 game add fun to the cozy environment.

Home in South Bend

Hot Tub | Backyard Oasis | Game Room | |Coffee Bar

Discover The Glendale Treasure 🏡, your perfect getaway hosted by Home Away From Home! This 4-bedroom, 2-bath home is packed with fun—swim in the heated pool 🏊, soak in the hot tub ♨️, or unwind around the firepit table 🔥. Inside, enjoy the coffee bar, the ultimate game room 🎮 with pool, air hockey, ping pong, and arcade classics. With cozy spaces and nonstop entertainment, it's ideal for families or groups. Book your stay today and make unforgettable memories!

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.

4.98 out of 5 average rating, 173 reviews

A fenced-in pool area features a clear water pool surrounded by a concrete deck. Lounge chairs and a dining set are positioned nearby, while a red umbrella offers shade. A slide is visible in the pool, with cornfields extending in the background under a cloudy sky.

Guesthouse in Cassopolis

Couples cottage with hot tub!

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our Blackstone or fire pit. Located in a small hobby farm setting with sheep roaming the pasture. We also have a couple cats that claim the pool area as their own. The long driveway and gravel road are perfect for a leisurely stroll to enjoy the great outdoors. Take a swim in the pool or a soak in the hot tub and let the worries of life melt away during your stay.

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 Kalamazoo 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, 27 reviews

A modern kitchen is presented with sleek white cabinetry and stainless steel appliances. An island with bar stools is centered, complemented by pendant lighting. Large windows offer a view of the outdoor area, allowing natural light to enhance the space.

Home in New Carlisle

Luxury home with pool.

5 out of 5 average rating, 39 reviews

Luxury Lake Michigan Escape w/Spa. Holiday ready!

4.95 out of 5 average rating, 42 reviews

Home in Saugatuck

Cedarwood Lodge

Superhost

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

The exterior of the house features a welcoming gray facade with a spacious porch. Colorful flower beds surround the property, and flags are displayed near the entrance. A curving driveway leads up to the home, enhancing its charm and accessibility.

5 out of 5 average rating, 37 reviews

Fern Creek | Pool, Hot Tub, Fire Pit, Chess | Dogs

4.96 out of 5 average rating, 79 reviews

An elevated wooden deck surrounds a circular blue pool, providing views of the nearby lake and trees. Multiple seating areas are arranged with tables and chairs, complemented by a shaded umbrella. Steps lead from the deck to the yard, enhancing accessibility.

Home in Allegan

Spacious Lakefront House - Amazing Views and Pool

4.98 out of 5 average rating, 148 reviews

A private in-ground swimming pool is surrounded by lush green grass and tall trees, offering a serene outdoor setting. Sun loungers are positioned nearby, with an umbrella providing shade. A colorful inflatable unicorn floats on the water, inviting relaxation in the sunny atmosphere.

Home in Douglas

Rustic Mid Century Pool Oasis. Steps from town!

5 out of 5 average rating, 40 reviews

A heated saltwater pool is framed by a sunlit deck with multiple lounge chairs overlooking a lush, tree-lined area. Surrounding greenery adds a sense of privacy, creating a tranquil outdoor space for relaxation.

Home in Saugatuck

Renovated Golf Course Home | Private Pool/Hot Tub

Condo rentals with a pool

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

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

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

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!

4.91 out of 5 average rating, 33 reviews

A spacious kitchen features warm wooden cabinetry and an expansive granite countertop. A round breakfast bar with stools provides seating, and modern appliances, including a refrigerator, are visible. Natural light floods the area through multiple windows, enhancing the inviting atmosphere of the space.

Condo in Saugatuck

Birds Nest | 2BR | Downtown Saugatuck

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

5 out of 5 average rating, 9 reviews

Cabin in Fennville

Lux Cabin Twin Peaks East • Private Pool & Hot Tub

4.99 out of 5 average rating, 89 reviews

A charming ranch-style house is situated on a spacious green lawn, surrounded by mature trees. The front features a welcoming porch with seating, and a driveway leads to an attached garage on the right. Lush landscaping enhances the tranquil setting.

Home in Sawyer

Fall Fun | Quiet Area | Huge Fenced Yard

5 out of 5 average rating, 11 reviews

A private heated pool is surrounded by a spacious deck shaded by lush trees. A hot tub is positioned nearby on the deck, complementing a rustic cabin with a blue metal roof. Outdoor furniture provides a comfortable space for relaxation.

Cottage in Sawyer

Harbert Home With Private Pool and Hot Tub

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

4.98 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

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

5 out of 5 average rating, 31 reviews

A spacious bedroom features a queen-sized bed with a striped duvet and matching pillows. Light blue walls complement the natural light from the window. A comfortable armchair and a decorative tree enhance the inviting space, while framed landscapes adorn the walls.

Apartment in Douglas

Summerset Cottage & Suites Queen Suite