Vacation Rentals With Private Indoor Pools

Looking for a vacation rental with a private pool that delivers relaxation and fun on your own terms? Terra2 offers vacation homes that combine privacy, poolside comfort, and Midwest charm. Our collection of homes near Chicago, Milwaukee, Minneapolis, or Cleveland delivers peace and quiet with impeccable amenities and splash-ready enjoyment.

A a house with a private indoor pool means you can swim regardless of the weather. Whether it’s rainy or snowy outside, your indoor pool remains available. Heated, well-lit, and secluded, these pools offer moments of calm, fun, or quiet laps any time of day or night.

Cleveland, OH

Bluffside Retreat

Escape to Bluffside Retreat in Willoughby Hills, where tranquility and luxury converge, just 30 minutes from downtown Cleveland’s vibrant scene. 

Learn More
Bluffside Retreat Pool
Chicago, IL

Highwood Haven

Unwind at Highwood Haven, an opulent McHenry getaway with a heated indoor pool and arcade. 

Learn More
Highwood Haven Pool 2
Rockford, IL

Cerro Vista

Discover the grandeur of Cerro Vista Estate, where luxury meets leisure in Rockford’s most sought-after vacation home. 

Learn More
Cerro Vista Pool 2
Minneapolis, MN

Valley View

Step into luxury at our expansive 5BR Twin Cities retreat, perfectly marrying comfort with elegance. 

Learn More
Valley View Pool
Milwaukee, WI

Wooded Hills

Discover the allure of our 5BR Wisconsin retreat, where spacious elegance meets comfort. 

Learn More
Wooded Hills Pool 2
Indianapolis, IN

Windrush

Less than an hour from Indianapolis, this unique retreat offers endless fun.

Learn More
Timberline Pool

Homes That Deliver Both Space and Amenities

Each of our vacation houses is designed for comfort and connection. Expect open layouts, chef-style kitchens, cozy living rooms, game areas, and hot tubs—all centered around the indoor pool. Our homes cater to families, groups, or multi-generational travelers. Stays in homes like Highwood Haven (Chicago area), Timberline (near Detroit), Cerro Vista (Rockford), and Valley View (Minneapolis region) offer room to relax, play, and gather easily.