Loop Haven
12 guests
6 bedrooms
Chicago Loop, Chicago
Welcome to The Jordan! Nestled in Chicago's iconic Chicago Loop, this urban oasis provides a tranquil retreat amidst the bustling cityscape.
Rent Illinois Homes with Swimming Pools
We selected the 6 homes worth renting in this location
Home spotlights
Large Glass of Red
24 guests
8 bedrooms
Napa County, California
Just outside of the village of Calistoga in the northernmost tip of the Napa Valley, you'll encounter this rustic yet refined retreat surrounded by acres of verdant vineyards and lush gardens. With no nearby neighbours, enjoy that all-too-rare feeling of seclusion, yet the convenience of only being a mile and a half from downtown Calistoga.
Redwood & Palm
6 guests
3 bedrooms
Santa Cruz County, California
Surrounded by hiking trails, golf courses, and stretches of Pacific coast, this home in Santa Cruz not only has an enviable location, but it’s bursting with the potential for plenty of memories made. The backyard, alone, has a private swimming pool, tiki bar, and a swath of green turf that the kids will love running around on – especially when they’re hiding from the dinosaur.
Chicago Heights
4 guests
2 bedrooms
Chicago Loop, Chicago
This pet-friendly apartment in Downtown Chicago puts the city right at your feet, with Millennium Park, The Art Institute, theatres, and shopping just a stroll away. Inside, floor-to-ceiling windows in the main bedroom frame the skyline, while a sleek kitchen with a breakfast bar and a light-filled living space make staying in just as tempting as going out.
We selected the top 3% holiday homes in Illinois Homes with Swimming Pools
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You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Illinois, United States. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Illinois Home to Rent with a Swimming Pool today, and set up a holiday to remember.
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