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 Detroit 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.

What Sets Terra2 Apart for Your Family Gathering?

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    Ownership & Management

    Our vacation homes are personally owned and managed. This means personalized care and prompt assistance directly from us.

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    Carefully Curated Homes

    We offer expansive, hand-selected homes with unique features, from free-to-play arcades to private heated indoor pools.

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    No-Chore Checkout

    Focus on family, not a checklist. Enjoy a true vacation, right up to the last minute.

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    Professionally Cleaned

    Arrive to high standards for cleanliness and enjoy our hassle-free checkout—no chore list required.

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    Book Direct & Save

    Booking directly on our website ensures you receive the best prices, no hidden fees, and access to future savings.

Amenities That Create Unforgettable Moments

Private indoor pool at a Terra2 rental

Luxury Indoor Pools & Spa Sanctuaries

Dive into luxury in our exclusive, heated indoor pools, promising year-round delight. Many homes also feature rejuvenating outdoor hot tubs and saunas, creating a private, spa-like experience for your family.

Private arcade room in a Terra2 rental

Private Arcades & Cinemas

Step into an exhilarating world of fun. Our homes feature entertainment-packed game rooms with free-to-play classic arcade games, billiards tables, and private cinemas for an unforgettable play experience for all ages.

Gourmet kitchen in a Terra2 family reunion rental

Large Gourmet Kitchens

The kitchen serves as the heart of the home, where culinary magic and communal joy blend seamlessly. Our fully stocked, gourmet kitchens feature state-of-the-art appliances and grand dining tables ready for your family feasts.

Spacious living room for family gatherings at Terra2

Expansive Gathering Spaces

Discover huge spaces where families and friends can relax and enjoy each other. From spacious living rooms with plush seating to expansive outdoor patios with fire pits, you'll find the perfect, elegant setting for connection.

Explore Our Collection of Luxury Pool Rentals

Our exclusive rentals feature private, heated indoor pools, offering year-round aquatic retreats just a short drive from major metro areas such as Chicago, Minneapolis, Indianapolis, and Detroit.

Terre Haute, IN

Deer Run Lodge

Set on 12 scenic acres, Deer Run Lodge offers families an exquisitely designed escape featuring an indoor pool, sauna, hot tub, arcade, and golf cart exploration.

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Chicago, IL

Highwood Haven

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

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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. 

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Cerro Vista Pool 2
Minneapolis, MN

Valley View

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

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Valley View Pool
Milwaukee, WI

Wooded Hills

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

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Wooded Hills Pool 2
Indianapolis, IN

Windrush

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

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Detroit, MI

Timberline

Escape to this 4-bedroom Shelby Township ranch featuring a private indoor pool, game room, and gourmet kitchen.

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Shelby Township 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.