Holiday rentals with a pool in South Bend

4.85 out of 5 average rating, 109 reviews

A large screened front porch is furnished with several wooden rocking chairs and a wicker seating area. Natural light filters through the screens, showcasing the surrounding greenery. A small table sits centrally, creating an inviting space for relaxation and conversation.

Cabin in Three Oaks

Cabin with POOL in family resort!

Nestled within a gated 67-acre resort and just minutes from the shores of Lake Michigan, this charming cabin offers a peaceful retreat ideal for couples, families, or solo travelers, blending rustic décor with modern comforts. Guests can spend their days exploring nearby nature trails, lounging by the pool, paddling across the lake, or unwinding on the porch. The perfect vacation for exploring nearby orchards and countryside, catching live music or theater, or just slowing down and recharging!

4.98 out of 5 average rating, 117 reviews

The heated in-ground pool features a diving board and a slide, surrounded by a spacious deck with lounge chairs and a shaded patio area. The inviting turquoise water reflects the clear sky, creating a relaxing outdoor space for leisure and enjoyment.

Home in Milford

Summer of fun Pool, Hot Tub, Huge Game Room CLEAN

From the heated in-ground pool, to the large hot tub, to the huge heated/a/c game room, you will love your stay at our Milford location. Created with comfort and fun in mind there is no end of things to do and places to unwind and enjoy the relaxation of a home away from home. With sizzling hot Wi-Fi, this place is perfect for a girl's weekend, a couples retreat, an extended stay with your family, or a work trip. All the details are well thought out to create a perfect getaway for every group.

4.92 out of 5 average rating, 121 reviews

A modern dining area features a wooden table surrounded by sleek black chairs. Behind it, a vibrant mural of South Bend adds color to the space. A cozy living area with a large sectional sofa and ample natural light can be seen through the open layout.

Home in South Bend

Large, Cozy, Theatre, Pool, Walk to ND Restaurants

Centrally located to walk & explore Notre Dame, restaurants, and all South Bend offers! Spacious 6-bedroom luxury home with open concept design, master suite w/ spa shower & jacuzzi, and balcony overlooking the pool with lounge deck. Theatre room w/ recliners, poker table & Xbox. Two large entertainment areas w/ 65” & 85” TVs, surround sound, blazing-fast WiFi, granite kitchen, large charcoal grill, fire pit, and comfy beds. Indoor & outdoor games make it perfect for families & game weekends.

4.99 out of 5 average rating, 219 reviews

Home in Vandalia

Quiet Couples' Retreat, Stock Tank Pool, Nature

Escape to you own private sanctuary in the heart of Michigan's beautiful countryside--surrounded by trees, birds, and wildlife. Leave the noise behind and reconnect in this romantic setting. Imagine sunning in our little stock tank pool, reading a book, or enjoying a cool drink. It is the perfect place for some serious soul care. Or visit the 45 minutes away touristy locations.....Amish Country Shipshewana, Lake Michigan, or Wine Country. Then, come back and enjoy the peace and quiet.

An outdoor view of the property showcases a wooden deck surrounding a heated plunge pool. The brown exterior of the house is framed by lush greenery, with seating areas and a gas BBQ grill visible. A secondary building is partially seen to the right.

4.99 out of 5 average rating, 106 reviews

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

SUMMER IS BOOKING FAST at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. ONE WEEK RENTALS ONLY DURING SUMMER, FRIDAY CHECK IN. This designer-owned haven offers both deep seclusion + an open-format layout that invites connection, healing + memory-making. Whether you’re gathering with family, reuniting with old friends, or seeking a rejuvenating escape, we deliver an experience that’s as comfortable + stylish as it is energetically charged.

4.86 out of 5 average rating, 223 reviews

A spacious green house features a traditional design with multiple windows on the upper level, bordered by well-maintained landscaping. A large driveway extends in front, accommodating parking for several vehicles, leading to a three-car garage with white doors.

Home in Union Pier

New Buffalo / Union Pier Pool Hot tub 7 Bedroom

Relax with the whole family at this peaceful home with Classic European style meets Lake Michigan! This astonishing turnkey home is the perfect escape from life in the busy city. The home is ideal for entertaining Famliy . 7 bed , 4 bath , hot tub and gas grille , close to union pier beaches and wine country . Property is nestled in a quaint country road location 1/2 mile off red arrow highway. Room for 10 cars,blue stone patios,ping pong table / game room . Pool open 5/20 to 10-1

4.97 out of 5 average rating, 236 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!

4.97 out of 5 average rating, 132 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.

4.92 out of 5 average rating, 334 reviews

A backyard oasis is showcased at dusk, with a heated pool reflecting warm lights strung overhead. Colorful pool floats gently rest on the water's surface, while a fire pit table is positioned nearby surrounded by Adirondack chairs, enhancing the inviting atmosphere.

Home in South Bend

Pool | Hot Tub | Backyard Oasis | Game Room | Fun

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!

Guest house in Cassopolis

An aerial view showcases a fenced-in pool area surrounded by lush green lawns and mature trees. A small patio with outdoor seating is visible beside the pool. The gravel driveway leads to the property, with an adjacent structure and a pergola enhancing the outdoor space.

4.97 out of 5 average rating, 193 reviews

Cottage for two with pool & 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.

4.92 out of 5 average rating, 115 reviews

A sparkling saltwater pool is surrounded by a spacious wooden deck, featuring lounge chairs and a shaded seating area beneath a roof. Lush green trees and vibrant landscaping provide a natural backdrop, while a fire pit is visible nearby, creating a relaxing outdoor retreat.

Home in Niles

Bibi's Retreat- Grand 7 Bedroom Private Escape

Bibi's Retreat-Nestled among 6,000 trees along 15 acres of secluded property. This is the ultimate private getaway. Located in Niles, MI, the home offers 7 true bedrooms with plenty of space for multi-family living. We are within 30 min of 15 wineries and breweries. We are within 20 min of 10+ golf courses and 20 min to Notre Dame. Ladies Retreat, Golf Getaway or Winery Tours, this home is perfect for large groups.

4.77 out of 5 average rating, 123 reviews

A wooden deck features two lounge chairs positioned for relaxation, overlooking a 24-ft above-ground pool surrounded by lush greenery. The deck showcases steps leading down to the pool area, enhancing outdoor accessibility.

Home in South Bend

Year Round Hot Tub, Outdoor Pool, 3 Bedroom & Bar

Experience the ultimate South Bend getaway! This charming 3-bed, 1.5-bath home is just steps from Notre Dame. Enjoy a 24ft pool 🏊‍♂️, 5-person hot tub ♨️, spacious deck with outdoor dining, and a BBQ grill. Inside, relax with a full kitchen, bar area, and washer/dryer for total convenience. Perfect for game days, family trips, and summertime fun—make lasting memories at The Poolside Retreat! ☀️🏡

Popular amenities for South Bend rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.86 out of 5 average rating, 44 reviews

A serene swimming pool reflects the soft colors of the sunset, surrounded by a cooling deck and lounge chairs. The peaceful ambiance is enhanced by the presence of trees and garden features in the background, creating an inviting outdoor space.

Home in Berrien Springs

FARM OF DREAMS

4.93 out of 5 average rating, 14 reviews

A bright and spacious backyard features a private pool surrounded by a wooden deck. Comfortable lounge chairs are arranged poolside, with a three-season porch visible in the background. Green grass frames the pool area, enhancing the outdoor relaxation space.

Home in Bridgman

The Poolside Escape | Hot Tub | Arcade | Ping Pong

4.95 out of 5 average rating, 20 reviews

A private swimming pool is surrounded by a spacious patio featuring a hot tub and comfortable seating areas. The home is positioned in the background, with large windows allowing natural light. A white picket fence encircles the area, providing privacy.

Home in Saint Joseph

Private Pool, Hot Tub & Outdoor TV

4.98 out of 5 average rating, 93 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

Heated Pool | Quiet Area | Huge Fenced Yard

4.96 out of 5 average rating, 92 reviews

Home in Sawyer

Atomic Acres-POOL, Summer 2026 Awaits!

A large heated saltwater pool is set in a manicured grassy area, surrounded by trees. The spacious house features multiple windows, reflecting natural light. Comfortable seating options are visible on a deck beside the pool, inviting relaxation in a private outdoor setting.

5 out of 5 average rating, 35 reviews

Private! Cherry Beach Pool House

Home in Chikaming Township

4.92 out of 5 average rating, 51 reviews

Stay Gold

5 out of 5 average rating, 93 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 Saint Joseph

4 Bedroom home w/pool in St. Joseph

Apartment rentals with a pool

Apartment in Stevensville

An aerial view of a resort area by Lake Michigan showcases several chalet-style buildings arranged around a spacious parking area. Lush green trees line the shoreline, and the calm water reflects the natural surroundings, emphasizing a serene environment. A sandy beach is visible nearby.

4.98 out of 5 average rating, 52 reviews

Sunset Pointe Chalet #31: Beach+ Pool + Games

A screened-in porch features a wooden circular table accompanied by four matching chairs. A cozy seating area with blue cushions and decorative pillows is also present. Natural light filters through the surrounding trees, enhancing the serene atmosphere.

4.73 out of 5 average rating, 11 reviews

Union Pier Condo with Association Heated Pool.

An outdoor dining area is featured on the screened-in porch, equipped with a wooden table surrounded by six metal chairs. A wall clock is mounted nearby, and a vase of flowers adds a pop of color to the table. Lush greenery is visible beyond the railing.

4.4 out of 5 average rating, 5 reviews

Union Pier Condo With Association Pool!

Apartment in Stevensville

An aerial view captures a cluster of charming chalets arranged in a semi-circle along the shoreline. The surrounding lush greenery and open parking area enhance the setting. Nearby, amenities such as pools and recreational spaces are visible, blending nature with community living.

5 out of 5 average rating, 66 reviews

Sunset Pointe Chalet #32: Beach + Pool+ Sports

A shared heated pool is featured in an outdoor area, surrounded by lounge chairs and greenery. A covered patio with seating is visible in the background, along with trees providing shade. Umbrellas offer additional sun protection over certain seating areas.

Union Pier Condo Close To Everything!

A screened-in porch is equipped with a large dining table surrounded by six chairs. Two lanterns are positioned on the table, enhancing the space's functionality. The porch features a blend of natural light and green walls, with a comfortable seating area for relaxation.

4.7 out of 5 average rating, 10 reviews

Union Pier Condo With Heated Pool.

A heated association pool is surrounded by a gated area and features a smooth, blue surface. Lounge chairs are positioned nearby, and a second level of the building is visible in the background, showcasing a spacious screened-in porch and a balcony.

5 out of 5 average rating, 6 reviews

Association Pool and Walking to Downtown!

Union Pier Condo With Heated Pool!

Other holiday rentals with a pool

A private pool area features a sparkling blue pool with a shallow entry and a floating pool lounge. Six lounge chairs are positioned under large umbrellas on a sun-soaked patio, offering shaded spaces for relaxation. The surrounding green trees provide a serene backdrop.

5 out of 5 average rating, 28 reviews

Updated Lakeside | Pool (Open!) + Hot Tub + Porch

4.97 out of 5 average rating, 29 reviews

The cabin features a wooden exterior with a large covered porch that spans the front. Surrounded by lush greenery, the expansive lawn leads up to the structure, creating a natural and serene setting perfect for outdoor activities.

Home in Union Pier

Private Cabin Retreat - Heart of Harbor Country

4.97 out of 5 average rating, 90 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!

A modern courtyard features a clear swimming pool surrounded by a paved area. Comfortable lounge chairs are positioned nearby, and lush greenery frames the space, enhancing the serene environment. Large windows provide visibility into the adjacent indoor areas, creating a seamless connection with nature.

5 out of 5 average rating, 19 reviews

Harbor Country Meets Modern- Pool, HotTub, EVChrgr

4.85 out of 5 average rating, 75 reviews

A clear view of the pool area is presented, showcasing a refreshing blue pool surrounded by a concrete patio. Lounge chairs and a dining set with an umbrella are positioned nearby, while a trampoline is visible in the background. The house features a deck with steps leading down to the pool.

Home in Saint Joseph

Updated 3 bdrm house w/ pool near beach & country

A spacious living area features high wooden ceilings and large windows allowing natural light to illuminate the room. Comfortable seating is arranged around a fireplace, with a small side table positioned nearby. A soft rug lies underfoot, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 39 reviews

Woodside

4.97 out of 5 average rating, 73 reviews

An overhead view of a well-equipped kitchen displays dark cabinetry and stainless-steel appliances. A light-colored marble countertop is accented by three round stools. A cozy seating area features a pair of blue chairs, with large windows allowing natural light to brighten the space.

Tiny home in Sawyer

Sandy Feet Retreat