Holiday rentals with a pool in Lake County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lake County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Home in Highland Park

4.91 out of 5 average rating, 145 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Guest favourite

Chalet in Ingleside

4.84 out of 5 average rating, 392 reviews

"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.

Guest favourite

Home in Grayslake

4.98 out of 5 average rating, 62 reviews

Family-sized Indoor Heated Pool & Movie Theater!

**HUGE INDOOR HEATED POOL**THEATER**SLEEPS UP TO 18 MAX** Set on a private and quiet property, this home boasts a 24/7/365 huge heated indoor in-ground pool attached to the house that is yours to use exclusively. The house has a private movie theater and fully stocked gourmet kitchen! Our occupancy is 18 max visiting or staying. Bring your well-behaved, house-trained dog to join you for no additional fee! **30 day rental available** You will not be disappointed!

Farm stay in Lake Villa

4.82 out of 5 average rating, 73 reviews

Bunk House at Susanna Farms

Within an hour of Chicago, you and your family can enjoy country life on this beautiful small farm. Surrounded by forest preserves on a quiet road so you feel like you're out in the country while still close to lots of stores and amenities. Say hello to the horses, chickens, goats, and sheep. Have a bonfire to roast marshmallows outside or enjoy cozy seating or large dining table in the great room. Full kitchen. Large living space and bedroom. No parties allowed!

Top guest favourite

Home in Waukegan

5 out of 5 average rating, 18 reviews

Great Lakes Family Getaway

Wonderfully remodeled multi-level home perfect for Navy family graduation stays or those returning to the area to visit. With 3 bedrooms/2 baths upstairs and 1 bedroom/1 bath on the lower level, there's plenty of room to spread out. You'll truly enjoy time with your loved ones in this beautiful retreat with a large yard that backs up to a golf course and includes a game room, screened porch and in-ground pool (weather permitting). 8 miles from GL Navy Base.

Home in Riverwoods

Riverwoods Nature Retreat

Make some memories at this unique and family-friendly place. A peaceful zen mid-century modern oasis. Relax in the hot tub. Play in the tree house. Tell stories by around the outdoor fireplace Curl up to a book in the hammock. Snuggle by the indoor fireplace and play Pictionary. Central to downtown Chicago, Lake Michigan, Milwaukee and Kenosha. We are a mid century paradise.