Holiday rentals with a pool in Lake County

4/2 Modern Luxury Home on Pistakee Lake with Pool

Welcome to "The Grand View on Pistakee Lake" — a stunning 4-bedroom, 2-bath lakefront Home perfectly positioned to capture breathtaking panoramic views over the water. This unique property offers the best of both worlds — Lake Life amenities and a prime location just steps from Fox Lake’s vibrant downtown. This unique property is the Penthouse Suite "so to speak" on top of a future fine dining restauraunt location, so it sits high above the water for breath taking views. And this is Pet Friendly

Kalo House | Mid-Century Modern Retreat with Pool

Step into a beautifully preserved mid-century modern home designed by noted architect Edward Humrich. The Kalo House blends iconic architecture with warm, curated interiors—clean lines, expansive windows, and thoughtful design throughout. Peaceful and stylish, it’s the perfect retreat for design lovers visiting Chicago’s North Shore, Lake Michigan, or nearby Great Lakes Naval Station. Thoughtfully, curated and hosted with care…Perfect for Navy graduation stays and gathering families together.

Bunk House at Susanna Farms

Just a short drive from Chicago, this charming small farm offers a chance to experience rural living. Nestled by nature preserves, you’ll feel immersed in the countryside while being conveniently near shops and services. Greet the friendly horses, chickens, goats, and sheep. Gather around a firepit or relax in the comfy seating or spacious dining area in the great room. The property features a complete kitchen, ample living space, and a comfortable bedroom. Please note, no parties, no pets.

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 throughout your stay! 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!

Navy Graduation Retreat- 4BR Home by Great Lakes

Wonderfully remodeled multi-level home ideal for Navy Bootcamp Graduation stays and family visits, located between Chicago and Milwaukee. With four true sleeping areas (3 BR/2 BA upstairs plus a private lower-level BR/BA), the home is well-suited for multi-generation comfort. Features include a large yard backing to a golf course, game room, screened porch, and seasonal in-ground pool (weather permitting). 📍 8 miles from Great Lakes Naval Base | 📍 5.5 miles from City of Hope – Zion

"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, June-October often cool to use in early June.

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.

Beautiful 137 Year Old Farm Home (3night min)

This beautiful north suburban farm home has updated and decorated for living a good life! Lake Forest public golf course is 1 block away. Downtown Lake Forest is withing a mile and the beach is 2 miles. Chicago is 30 miles with train access.

New Net Zero Energy Building- 5 day minimum

This unique place has a style all its own.