Holiday rentals with a pool in Will County

Relaxing 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!

Best view and luxury style, Located in Downtown

Experience the best view of your life Chicago's iconic landmarks from this high-rise apartment. Located downtown,you can see Wacker Drive, the lake, Navy Pier, the river,Trump tower from your balcony and room , The place features a spacious bedroom with a king bed , comes fully equipped with essentials, kitchen. large TV, and high WiFi. With premium amenities pool, spa, hot tub, library ,work area,computers,gym, bar. offers the perfect blend of luxury, comfort for a best city life experience

Glamping Yurt&RV Gaming Room Pool/Hotub/Court more

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Mini Resort Includes: RV w/bathroom - 2 beds & sofa 20' Safari Yurt - 4 beds Gaming Room w/bathroom 1 bed & sofa sleeper Xbox Series X & PS5 Disc Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Breakfast included is 1 dozen fresh eggs! Additional Event Yurt add on $180 up to 15 additional non/overnight

Peaceful backyard oasis. Unique!

Minutes from Naperville, 30 minutes to Chicago yet you feel like you are in the country in the backyard. The home backs up to wooded lands. Sipping coffee in the backyard you’ll have many choices of where to hang out. You’ll see Blue Jays, Cardinals, yellow finches, woodpeckers, hummingbirds among many other water birds and high flyers. You may even see a coyote or two roaming. In the evening you’ll see many deer and beautiful skies at sunset. Pool, pool table and fire pit. Large rooms.

Special Occasion Glamping & Event Space Yurt

Look no further for your small event space! This unique Glamping experience on 2 acres of land will leave you and your guest full of memories! Opened May - Oct. Pickleball/basketball/volleyball Court Swimming-2 hot tubs-a sauna-Game Room- 4 grills and hibachi-30' Event yurt-20' Safari yurt-A-Frame cabin w/bathroom-RV w/bathroom-Game room Suite w/bathroom-20' Tent-Screened in Gazebo. Spacious Event Space Yurt & Pavilion also includes: Seating, Hot & Cold Buffet, Throne Chairs, Tables

Spacious Family Glenwood Estates Home w/ Hot Tub!

Find your new favorite spot in the suburbs of Chicago when you stay at this 4-bedroom, 2.5-bathroom vacation rental! This spacious home has a fantastic backyard to relax in with a seasonal pool, a hot tub, and an outdoor dining table. Head downtown to explore the area with shopping on the Magnificent Mile, dining with a view on the Navy Pier, or sightseeing on the Chicago Riverwalk. On your way home, grab some Chicago-style pizza and relax in the living room next to the fireplace!

Hidden GEM OASIS in Chicagoland with inground POOL

STRICTLY NO PARTIES and EVENTS Allowed. Automatic cancellation with No refund will be applied if this rule is violated. Nestled on 2 1/2 acres, this 4 bedroom, 2.5 bath oasis boasts a host of desirable features. The corner lot location ensures privacy, complemented by a relaxing screenhouse and a spacious outside patio, perfect for entertaining or quiet evenings under the stars. Pool Season June 1 -sept 22 2025.

New! Modern Retreat with Private Pool & Yard

Discover the perfect blend of comfort and convenience at this stylish Orland Hills getaway! This spacious vacation home features a private backyard oasis complete with a sparkling pool (**Undergoing Repair/Replacement**), perfect for relaxing summer days or entertaining the family. The fully fenced yard offers both privacy and peace of mind, whether you're enjoying a quiet morning coffee or an evening cookout.

Tranquil Coachhouse Studio Apartment

Relax in a Skylit Second floor Studio apartment on a Private Lane in a Tranquil setting. Near I-57. 40 minutes south of downtown Chicago. Check-in and out time is usually flexible.