Vacation rentals with a pool in South Haven

An indoor heated pool is surrounded by sleek tile flooring and ceiling-mounted ventilation. A colorful mural depicting a sunset over water enhances the space. Pink inflatable flamingos float on the water, alongside blue inner tubes. Comfortable lounge chairs with striped cushions are arranged nearby.

4.96 out of 5 average rating, 100 reviews

Nautical Retreat – Indoor Pool, Sauna, HotTub MORE

Chill & Thrill Nautical Retreat is a spacious 4BR/3BA home that sleeps 12, perfect for family vacations or group getaways. Just a short walk from downtown and central to both beaches, it offers endless fun for all: unwind by the indoor heated pool, relax in the 7-person hot tub, or play arcade games in the loft. Lounge in the hammock triangle, play lawn games, or enjoy cozy nights by the fire pit. Create lasting memories in the ultimate vacation retreat, with South Haven as the perfect backdrop!

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.

5.0 out of 5 average rating, 259 reviews

Driftwood Shores/SH Fall colors & a beautiful lake

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.

5.0 out of 5 average rating, 117 reviews

The exterior of a two-story home is visible, featuring a welcoming front entrance. A large tree provides shade, with a swing hanging from one of its sturdy branches. Ferns line the landscape, creating a natural border around the property, complemented by a well-maintained lawn.

Home in St. Joseph

4 Bedroom home w/pool in St. Joseph

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

4.92 out of 5 average rating, 193 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.

4.98 out of 5 average rating, 126 reviews

Halloween & Christmas Fun- Pool - South Haven, MI

Celebrate the holidays here - Decorated for Halloween in October and Christmas in December! Year round community pool! The ultimate family getaway! Perfect for families with kids or for groups/individuals looking for a fun 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.

4.97 out of 5 average rating, 102 reviews

Apartment in South Haven

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

Central Lofts condos used to be the old Central High School. We are located in downtown South Haven. Stay 2 blocks from the Farmer’s Market, also an ice skating rink in winter. The building has a shared indoor pool and hot tub, 2 old fashioned private movie theaters (seats 12), fire pit, and an exercise room. This cute condo has a king bed and twin sized trundle bed in master bedroom, and two pullout couches in living room. Walk to town & the beach, .7 miles to S. Beach and 2 blocks to town.

4.99 out of 5 average rating, 102 reviews

Apartment in Coloma

Awesome Family Escape with pool and private beach

Fun summer getaway with the family or a group of friends at this hidden gem in Southwest Michigan! This peaceful condo features 2 bedrooms with 3 brand-new beds(1 king and 2 queen) comfortably sleeping 6, and 2 full bathrooms. Equipped with two work-from-home desks and high-speed internet, it’s perfect for balancing work and relaxation. Enjoy the full kitchen, washer and dryer, cable TV, and all you need for fun!! Relax on the private beach, just a short walk or hang at the private pool.

4.96 out of 5 average rating, 206 reviews

The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.

Home in Michigan City

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Beautiful home in the heart of Beachwalk, across the street from Lake Kai, pools, basketball & tennis courts and 2 blocks to Lake Michigan. This home is bursting with charm. Front porch runs the width of the house. Dining area opens up to family room with a lovely fireplace. Stunning master bedroom w/walk-in closet and beautiful new bathroom with all the finishes. 3 more bedrooms upstairs, one with full bathroom attached and the other 2 sharing bathroom. 5th bedroom on the lower level.

4.97 out of 5 average rating, 120 reviews

A bedroom features a spacious bed adorned with white linens and a navy throw blanket. Exposed brick walls add character, complemented by framed ocean-themed art. A mirrored dresser and a closet with hanging space provide ample storage. Natural light filters through a nearby window.

Apartment in South Haven

Indoor pool & hot tub: Walk everywhere: Gym

✨Upscale historic loft building 🚶WALK EVERYWHERE 🕑 2:00 PM CHECK-IN ⭐️Central Loft amenities⭐️ ♨️ Hot tub 🏊‍♂️ Indoor heated pool 🎬 2 movie theaters 💪 Workout room 🏖️ Beach necessities included 🌊 1/2 mile to Lake Michigan 🛍️ A block from downtown SoHa 🍷 Near The Lakeshore Wine Trail 🍺 Close to several breweries 🧺 Washer & dryer in condo ☕️ Keurig & standard brewing coffee pot 🧑‍🍳 Fully stocked kitchen ⚡️ High speed internet 📺 Smart TV

4.96 out of 5 average rating, 104 reviews

An inviting pool area is surrounded by a wooden deck, featuring comfortable seating arrangements and a large red umbrella providing shade. Lush greenery stands tall in the background, complementing the serene atmosphere of the private fenced space.

Home in Lakeside

Lakeside with heated pool & pvt beach access!

LAKESIDE COTTAGE - POOL, HOT TUB & RARE semi-private Lake Michigan access to gorgeous beach shared by just 10 homes, so it’s never crowded! Beach access is a 7-min walk away (no parking). The pool will close Sept 16th, 2027 this year! Charming, sun-filled cottage sleeps 8 (3BR + pull-out). Heated 85 degree pool (May 22–Sept 15), new hot tub, fire pit, gas fireplace, spacious deck, bluestone patio & grill. 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!

4.97 out of 5 average rating, 139 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.

4.94 out of 5 average rating, 143 reviews

Home in New Buffalo

New buffalo Farmstead main home pool hot tub

5 bedroom 2 bath 2200 sq ft modern farmstead , 2 minutes to new buffalo and beach and all its offerings , 18x36 new heated shared pool open 5/20 to 10/ 20 and hot tub open year round maintained at 104 f . Property on 3 acres with plenty of room for kids to play , 26 apple trees and woods , ride host bikes to new buffalo .. Best of both worlds in country , close to town .There’s 1 other home on 3 acre property, this home and 1 guest home ( rented separately) .

Popular amenities for South Haven rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 103 reviews

Home in Sawyer

Atomic Acres- Pool, Hot tub, Fire pit & more

4.85 out of 5 average rating, 112 reviews

A spacious outdoor area features a hot tub beside a well-maintained pool. Lounge chairs are positioned around the pool, with a covered seating area in the back. A wooden pergola provides shade, while string lights add a touch of ambiance.

Home in Three Oaks

Play @ The Hideaway - hot tub, sauna, gymnasium

4.94 out of 5 average rating, 170 reviews

A spacious deck surrounds a hot tub, with comfortable loungers positioned nearby. In the background, lush greenery frames an open field, and a wooden bridge spans a small area, enhancing the natural setting of the property.

Home in Berrien Springs

18-acre pond retreat | Heated pool & hot tub

4.94 out of 5 average rating, 108 reviews

A hot tub is shown with bubbling water, positioned beside a spacious heated pool surrounded by lush green grass and trees. A wooden deck features a gas BBQ grill, and lounge chairs are placed nearby for relaxation.

Home in South Bend

Pool | Kayaks | Hot Tub | Game Rooms | Sleeps 15

4.95 out of 5 average rating, 153 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

4.98 out of 5 average rating, 100 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 Bridgman

Cozy Ranch | Huge Fenced Yard| Fall Fun

4.82 out of 5 average rating, 177 reviews

A gated pool area is shown, featuring a vibrant blue swimming pool with floating toys. Surrounding the pool is a concrete deck and a green fence. A white chair and a basketball hoop are visible in the background, adding to the outdoor recreation space.

Home in Holland

Welcome Home *Near Lake Mi Beaches and Downtown*

The outdoor area features a sparkling pool surrounded by lounge chairs and umbrellas. A spacious patio is equipped with a large dining table and additional seating, offering a perfect setting for relaxation in a beautifully landscaped backyard.

4.97 out of 5 average rating, 32 reviews

Resort Pool Home | Walk to Beach | 7 BR | Dogs

Condo rentals with a pool

4.98 out of 5 average rating, 123 reviews

Condo in South Haven

SunKissed Sanctuary + Pool + Hot Tub +CentralLofts

4.97 out of 5 average rating, 271 reviews

Condo in Douglas

Fun condo with open pool through September!

4.89 out of 5 average rating, 150 reviews

A charming two-story building is framed by mature trees with vibrant green leaves and autumn accents. The front door, painted bright yellow, is flanked by decorative lanterns, while large windows with dark shutters provide a welcoming facade. Lush greenery surrounds the entrance.

Condo in Saugatuck

Robyn's Chain Ferry Nest #2

4.93 out of 5 average rating, 105 reviews

A modern living room features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, while two lamps provide soft lighting. Artwork adorns the wall above, accompanied by a round mirror reflecting the space.

Condo in New Buffalo

Nightingale Dunes - Modern beach town retreat

4.9 out of 5 average rating, 101 reviews

A dining area features a wooden table surrounded by six chairs, creating a space for gathering. A spiral staircase leads to an upper level, while nautical-themed decor adorns the walls. An adjacent open doorway reveals additional kitchen space, enhancing the home's inviting layout.

Condo in New Buffalo

New Buffalo Getaway Condo

5.0 out of 5 average rating, 27 reviews

A studio condo features a queen-size Murphy bed with a light-patterned blanket and a cozy futon nearby. A small dining area with a table is positioned adjacent to the fully equipped kitchenette. Soft blue walls and natural light create a relaxed ambiance.

Condo in South Haven

Private Beach/Pool on Lake MI Condo

4.98 out of 5 average rating, 65 reviews

Condo in Saugatuck

Couples waterfront getaway close to beach & trails

5.0 out of 5 average rating, 21 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 vacation rentals with a pool

4.89 out of 5 average rating, 122 reviews

The cabin exterior features a warm wooden facade under a canopy of trees. A spacious covered porch with a wooden railing is visible, enhancing the inviting entrance. Two dormer windows add character to the sloping roof, providing a cozy appearance.

Cabin in Saugatuck

Foxtail Hideaway-Luxury Cabin in Kingfisher Cove

4.99 out of 5 average rating, 68 reviews

Cottage in South Haven

Cheerful Cottage, Walk to beach, Private Pool

4.97 out of 5 average rating, 75 reviews

Modern Koi Getaway: 3BR Near Lake Michigan Beaches

5.0 out of 5 average rating, 24 reviews

Cabin in Fennville

Lux Cabin Twin Peaks East • Private Pool & Hot Tub

5.0 out of 5 average rating, 7 reviews

Cherry Blossom Cottage New 6-person LSV/Golf Cart

4.95 out of 5 average rating, 42 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, 69 reviews

A modern home is situated on a sandy lot beside a small private lake. Large windows reflect the surrounding greenery, while a sloped roof adds to the architectural design. The outdoor seating area is visible, enhancing the tranquil setting.

Home in Stevensville

Bright & Modern Home: Heated Pool Open 5/20-10/13