Holiday rentals with a pool in South Haven

4.96 out of 5 average rating, 131 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, 229 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.

5 out of 5 average rating, 204 reviews

The exterior of the cottage features vibrant blue siding and a covered porch with white railings. Lush greenery and landscaped beds surround the entrance, creating a serene and welcoming façade. A pathway leads to the front door, inviting guests into the home.

Home in New Buffalo

Designer Cottage - walking distance to downtown

Dream cottage getaway just over an hour from downtown Chicago. Walking distance from the beach, restaurants and all of downtown New Buffalo. Close to the casino, wineries and breweries. Whether driving in or taking the train, The Bradford is a relaxing yet sophisticated getaway. Eat, drink, and enjoy the beach, the pool, the shops and incredible summer sunsets, all within walking distance! Please note pool/bathhouse open late May - September and is shared with our association.Permit C22-0051

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, 105 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.

4.88 out of 5 average rating, 135 reviews

A stone pathway leads through lush greenery and colorful flowerbeds toward a light-filled, glass-fronted structure. Towering trees create a natural canopy, enhancing the serene atmosphere of the garden setting.

Home in Three Oaks

Experience Fall Beauty & Harbor Country Charm!

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closes October 10, 2024 through Memorial Day 2025 After a day of exploring the waters of Lake Michigan, Warren Dunes, or nearby wineries, find your sanctuary at Mae's Place. Recharge by soaking in the inviting hot tub, sizzle up a delicious meal on the grill or in the kitchen and end the evening roasting marshmallows around the fire pit or watching an outdoor movie on the pool deck.

4.97 out of 5 average rating, 236 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.

Apartment 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, 124 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)

4.96 out of 5 average rating, 226 reviews

A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.

Cottage in Union Pier

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today! Create lasting memories!

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

Romantic getaway and/or family adventure Quiet updated farmhouse on a quiet road 5 miles from South Haven and Lake Michigan.The Black River runs along the property and there are 3 ponds.There is secluded in ground pool,woods and landscaped grounds for walks Great local markets A guest made a video about his time at the cottage that you can see on You Tube. GoozyVision Trip to South Haven,Michigan July 2017 The video also shows the beach and the town

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, 227 reviews

Driftwood Shores-Enjoy a Winter Getaway!

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.

Guest house in Cassopolis

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.

4.98 out of 5 average rating, 174 reviews

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, 137 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 South Haven rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.78 out of 5 average rating, 9 reviews

A spacious screen porch is highlighted by large windows allowing ample natural light. Comfortable seating arrangements include black wicker chairs and a circular coffee table, with a view of the private heated pool visible through the glass. The wood-paneled ceiling adds warmth to the space.

Home in Union Pier

Union Pier Home With Private Pool!

4.88 out of 5 average rating, 8 reviews

A spacious outdoor pool area is framed by a stone patio, featuring several lounge chairs arranged neatly around the pool. The modern vacation home is visible in the background, with large windows allowing natural light to fill the interior. Lush greenery surrounds the property.

Home in Union Pier

Living My Best Life w/ Private Gordon Beach Access

4.94 out of 5 average rating, 166 reviews

A private hot tub is set in a wooden enclosure, surrounded by a serene natural landscape. Steps lead up to the hot tub, offering easy access. Two white Adirondack chairs are positioned nearby, inviting relaxation in the peaceful outdoor setting.

Home in Union Pier

Winter & Holiday Couples getaway Pvt Hot tub

The exterior of a modern cottage is showcased, featuring a two-story design with white siding, black shutters, and a charcoal-colored stone accent. A well-maintained front yard with shrubs and decorative gravel complements the entrance, which includes a covered porch and a single-car garage.

4.97 out of 5 average rating, 60 reviews

Luxury cottage, near beach & town, pool & hot tub

The cottage features a light blue exterior with a covered front porch that includes rocking chairs and a welcome sign. Bright windows allow for natural light, while lush greenery borders the property, providing a serene setting. The two-story structure boasts a classic design with white railings.

5 out of 5 average rating, 5 reviews

Downtown Dream

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

The exterior of a two-story house is shown, featuring light grey siding and a welcoming entrance with lavender double doors. A spacious deck with white railings provides access, surrounded by a green landscape and blue sky.

5 out of 5 average rating, 24 reviews

The Peacock

A tastefully arranged living room features a spacious leather sofa and black armchair, accompanied by a light wooden coffee table. A patterned area rug adds warmth, while large windows invite natural light. Contemporary artwork adorns the walls, contributing to the modern design aesthetic.

4.97 out of 5 average rating, 64 reviews

Modern Koi Getaway: 3BR Near Lake Michigan Beaches

Apartment rentals with a pool

4.88 out of 5 average rating, 180 reviews

A bright living area features a red couch adorned with blue and white decorative pillows. Two patterned armchairs complement a white coffee table, set on polished wooden flooring. Large windows allow natural light, enhancing the warm atmosphere of the space.

Apartment in Saugatuck

Robyn's Nest Riverside-Nautical Nest #6

5 out of 5 average rating, 17 reviews

Apartment in Saugatuck

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

5 out of 5 average rating, 21 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.

Apartment in South Haven

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

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.

Apartment in Douglas

Northern Lights 2 Bed 2 Bath With Pool

5 out of 5 average rating, 5 reviews

An outdoor pool is surrounded by lounge chairs, providing a relaxing area for guests. The three-story building features balconies on the upper floors. Clear blue skies add to the inviting atmosphere, enhancing the setting for relaxation and leisure.

Apartment in New Buffalo

Fall 2 nt min Perfect Location Condo Pools Walk to

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.

Apartment in Coloma

Amazing Beach Condo with pool and great sunsets!

5 out of 5 average rating, 24 reviews

Apartment in South Haven

South Haven North Shore condo

4.91 out of 5 average rating, 34 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.

Apartment in Saugatuck

Birds Nest | 2BR | Downtown Saugatuck

Other holiday rentals with a pool

5 out of 5 average rating, 28 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.

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.

Flat in South Haven

North Shore Hideaway

Townhouse in Saint Joseph

5 out of 5 average rating, 9 reviews

Marina Sunset: Savor Fall Flavors in Saint Joseph

Campervan/Motorhome 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*

Holiday home in Stevensville

An aerial view captures a lakeside community featuring numerous chalet-style homes. Lush greenery surrounds the area, with the shimmering expanse of Lake Michigan visible in the background. A swimming pool and recreational facilities can be seen, along with parking areas and sandy volleyball courts.

4.93 out of 5 average rating, 69 reviews

A-Frame On Lake Michigan - beach, sports, + pool

5 out of 5 average rating, 3 reviews

Flat in Douglas

Modern Coastal Retreat w/ Pool – Walk to Downtown!

4.97 out of 5 average rating, 34 reviews

Home in Saugatuck

Waterfront Retreat w/ Pool • Walk to Downtown