Holiday rentals with a pool in Will 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!

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

30 mins to CHI•3 Kings•BBQ Grill•Spacious•Pool

Discover the timeless charm of this 2,400ft² farmhouse, where character meets comfort. Soak up the sun by the in-ground pool with loungers, or enjoy a firepit for cozy nights. Fire up the BBQ grill or sip drinks at the granite bar. Inside, relax in the cozy seating areas, gather around the large dining table, and enjoy the immense, fully equipped kitchen. ★ 5 minutes to downtown Plainfield ★ 20 minute drive to Naperville ★ Just a 30 minute drive into Chicago Come enjoy Plainfield with us!

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!

Your favorite vacation spot

Tucked away on its own private spot sits a home you will truly enjoy. This 4 Bedroom 3-1/2 Baths oversized Quad level home catering to every family member’s needs from a relaxing to an activity filled day, it is 5 mins away from forest preserves and less than an hour from Chicago’s downtown. Sitting on 2 acres of tree lined land inside you'll find this home has been custom built with exceptionally large spaces. It has a beautiful outdoor swimming pool and a sunroom with jacuzzi

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, 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.