Holiday rentals with a pool in South Bend

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!

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.

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.

Anchors Away - Sawyer, MI

Welcome to our home! We are so excited to get to share our home with you! Our family-friendly has a cozy living room, fireplace and a full kitchen! On site is a heated pool, laundry mat, and it’s home to the Beach Bucket the best spot for amazing ice cream, homemade popcorn and fudge! Directly across the street is Warren Dunes State Park. The 3/4 mile walk, drive or bike ride gets you to the beach for a fun filled day! Climb the dunes, lay in the sand, go for a swim, relax-you’re on vacation!

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.

Play @ The Hideaway - hot tub, sauna, gymnasium

Accommodating up to 22 guests, this expansive 5,891 sqft property is set on 22.6 acres, creating a private oasis complete with a pool, hot tub, sauna, and gymnasium. The residence features a Great Room, fireplace, fire pit, and a private trail, making it an ideal setting for relaxation and recreation. With 3 king-size beds, 4 queen-size beds, and 2 bunk beds with trundles, comfortably catering to the needs of large groups. This venue offers enjoyable experiences for guests of all ages.

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.

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.

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!

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.

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.

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! ☀️🏡