
Vacation rentals with a pool in Michigan City
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Michigan City
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Romantic Spa Getaway -Private Jacuzzi, Sauna, Pool
Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

Private Cottage in Gated Nudist Community
We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is mandatory. Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental.

Charming 2BR/2BA Cottage with Full Kitchen & Patio
The cottages, or townhouses, are situated steps away from the main inn, providing an added sense of privacy while still feeling the vibe of the community. This cottage has two bedrooms (one with a queen bed in the downstairs bedroom + another with 2 twin beds in the upstairs bedroom). Two bathrooms (one upstairs, one downstairs) keep things fresh with a queen sleeper sofa. The upstairs loft space provides extra room for rest. An in-unit washer/dryer and high speed WiFi makes things easy.

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.

Wabi Sabi Chic at The Flamingo Ranch in Lakeside
NOW BOOKING SUMMER 2026 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 Barn Camper' w/Hot Tub near Indiana Dunes
Hot tub open all year! Pool will reopen May 1. Fully equipped RV sleeps 5, has bathroom w/shower, stove, microwave, TV, heat & A/C, & running water all year. Located on the bike trail & only minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hike in the Indiana Dunes National Park along the Little Calumet River & the historic Bailley homestead, only 1 block from the RV. Enjoy our large pool, hot tub, grill, campfire, & playground too. Schedule your visit today!

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!

Casa Playa - Union Pier Home w/ Pool & Private Spa
This 4 bedroom getaway is located in the heart of Harbor Country and is just a 10 minute walk or 3 minute drive to the best beach in Union Pier! Casa Playa has EVERYTHING a vacation house can offer: an association POOL, a private HOT TUB, high speed internet that accommodates many people working from home, a cozy indoor fireplace, an outdoor fire pit, an outdoor deck & grill, 2 smart Tvs, ALL brand new appliances, and games for the whole family!

Cozy cottage for two 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.

Lagunitas Coach House in Beachwalk, Lake Michigan
Lagunitas Coach House is a sought after location on the quaint Thomas blvd cul de sac. It is the coach house to Gooch Life. It is the perfect get away spot for a couple or small family wanting to escape to the beautiful beach of Lake Michigan. Lagunitas and Gooch Life share the property but are separate structures. Lagunitas has a private entrance, amenities, and parking. Lagunitas sleeps 6, see pictures for bed configuartion.

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 and hot tub. Property on 6 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 2 new homes on 6 acre property, this home and 1 guest home ( rented separately) .

Beautiful home in Beachwalk/Notre Dame weekends
Enjoy the open concept family room/dining area, flat screen TV, fireplace, and a farmhouse table that seats 12. You can also enjoy the sunset from the top floor "birds nest" with views of the Chicago skyline. The lower level is perfect for kids to watch TV and play games and is equipped with bunks that sleep up to 7 people. A Staircase leads to a private walkway for access to Lake Michigan.
Popular amenities for Michigan City rentals with a pool
House rentals with a pool

Luxury home with pool.

The Poolside Escape | Hot Tub | Arcade | Ping Pong

Fall Fun | Quiet Area | Huge Fenced Yard

Lake House – Pond & Pool Access

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

Hilltop Cove- Beautiful 2 bed/ 2 bath in Beachwalk

Private Pool, Game Room, Fire Pit, Near Downtown

Winter Wonderland- Perfect Family Getaway!
Condo rentals with a pool

Large 3BR w/ pool and parking - near everything

(2026 OPEN!) Union Pier Condo With Heated Pool.

2026 Open Perfect Location Condo Pools Walk to all

Nightingale Dunes - Modern beach town retreat

New Buffalo Condo with Association Pool and Beach!

Sunset Pointe Chalet #31: Beach+ Pool + Games

Sunset Pointe Chalet #32: Beach + Pool+ Sports

New Buffalo Getaway Condo
Other vacation rentals with a pool

Marina Sunset: Snowy Saint Joseph Awaits You

| Fire Pit | Hot Tub | Dog Friendly

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

Stay Gold, a Sawyer retreat

Cozy Mid-Century Home•Private Pool• Dog-friendly!

Family Tides at Harbor Shores

Farm Themed Guesthouse!

Resort Villa with Pool and Hot Tub
When is the best time to visit Michigan City?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$72,663 GYD | G$62,282 GYD | G$80,967 GYD | G$80,344 GYD | G$106,918 GYD | G$144,288 GYD | G$154,668 GYD | G$154,876 GYD | G$94,877 GYD | G$80,967 GYD | G$63,113 GYD | G$86,365 GYD |
| Avg. temp | -4°C | -3°C | 3°C | 9°C | 15°C | 20°C | 22°C | 22°C | 18°C | 11°C | 4°C | -1°C |
Quick stats about vacation rentals with a pool in Michigan City

Total vacation rentals
Explore 140 vacation rentals in Michigan City

Nightly prices starting at
Michigan City vacation rentals start at G$18,685 GYD per night before taxes and fees

Verified guest reviews
Over 2,140 verified reviews to help you choose

Family-friendly vacation rentals
130 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
140 of Michigan City vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Michigan City rentals

4.8 Average rating
Michigan City stays are highly rated by guests—averaging 4.8 out of 5!
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Soldier Field
- Guaranteed Rate Field
- The Field Museum
- Warren Dunes State Park
- University of Notre Dame
- Wicker Park
- Oak Street Beach
- Garfield Park Conservatory
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Washington Park Zoo
- The 606




