Vacation rentals with a pool in Kane County

Beautiful Spanish style Home (w/inground pool)

Experience a mix of old and new at this recently renovated Spanish style villa. Casa Dra’eh – less than an hour from Chicago! Staying for business or leisure, this stylish retreat offers the perfect blend of sophistication and comfort. Relax on the private rooftop balcony overlooking the backyard , featuring a pool and veranda ideal for dining. Cook in the chef’s kitchen or unwind in modern Spanish decor. With Chicago just a short drive away, enjoy the best of both worlds. Book your stay today!

Grand 1800s Victorian Gem: Updated/by Downtown

Step back in time with this Victorian, pet friendly, home featuring original pocket doors, gorgeous inlaid floors, & sparkling leaded glass windows. You will feel right at home with the comfort of the updated kitchen and baths with tons of space for all sized groups. This home is just three blocks from downtown Woodstock where you can dine, shop, & visit the famous opera house. Don't forget to visit the many scenes the movie Groundhog Day was filmed at throughout town and toast to world peace!

Haven Estates_: Cozy Barn, Hot Spa & heated Pool

Enjoy a peaceful countryside retreat at this charming Barndominium set on 6.5 private acres, accommodating up to 8 guests This spacious getaway features an 18' x 36' private pool with a hot spa and a solar-heated pool room for year-round relaxation. The Great Room offers open-concept living with comfortable seating, recreation space, and four sleeper sofas. The cozy bedroom includes a king-size bed, while the fully equipped chef’s kitchen boasts an oversized island & a stove with an air fryer.

Spacious 3 Floor Townhome

Beautiful spacious 3 floor townhome in perfectly located area. Driveway parking for up to 2 vehicles, backyard area with grill, making your stay comfortable and giving a home vibe. NO parties or events are allowed to be hosted .Master bedroom comes with King size bed , walk in closet , and half closet. Property is by I90 for quick access to O’Hare and Chicago. Walking distance to convince stores and 5 miles or less to Woodfield Mall, Golf Courses , Congo River Mini Golf and so much more.

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

"A" Frame Brandenburg Lake

Getaway to a cozy 1 bedroom w/loft for 2, up to 6 people. Full kitchen 1.5 bath all season getaway. There is a piano as well. A tranquil home steps from a private lake. Oak and Pine surround you plus a stone fireplace, it feels like the North Woods. The A Frame guest house shares a 5 acre compound ( total 20 Acres) with the owners residence and caretaker cottage. The Volo Bog 800ft away. No hot tub Nov - May. Swimming pool usually June-October often cool to use in early June.

Cozy & Relax Escape

You are booking a Cozy, Modern, and SPACIOUS Basement Apartment with a Private Entrance, and a large open-concept Guest Suite! Located in one of West Chicago incorporated quiet neighborhoods. Host occupies the separate 1st floor. You’ve your own private entrance & space. No SHARING!! Why Share if you can have your own private space for a reasonable rate. Pool is available for rent.. Max 15 people allowed! Inground heated pool with deep & shallow end. Pool size 16x22.

Upscale, Smoke and Pet Free, Washer Dryer, Balcony

If you’re looking for the ideal place to feel at home that's affordable, close to Downtown Chicago, Wheaton, Oakbrook, shopping, dining, highways, there’s nothing better than this fully furnished Penthouse unit. It's recently renovated, offers the modern conveniences you could want. It includes everything you need from free parking, linens to dishes, cookware, cable, wireless internet, king size bed, in-unit washer - dryer, 2 smart TV’s, LED fireplace, and Netflix.

Cloud 9: 4BR, Pool, Fully Fenced

This inviting two-story home is designed for comfort, entertainment, and relaxation. The pool is officially open for the season! Kids love this place—there’s a sandbox, water table, and swings to keep them busy for hours. Enjoy the open-concept layout, a loft for work or reading, and a fun lower-level game room with a pool table. Outside, soak up the sun with outdoor dining, lounge chairs, and plenty of space to unwind. This 4 bedroom home is perfect for your stay!