Vacation rentals with a pool in Will County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Will County

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Guest favorite

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. An island with bar seating is positioned in the foreground, while a spacious archway leads to an elegantly designed hallway featuring artwork and natural light.

Home in Plainfield

4.94 out of 5 average rating, 80 reviews

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!

An expansive outdoor space showcases a landscaped backyard with an in-ground pool, surrounded by a protective fence. Loungers are positioned around the pool, and a covered seating area is visible, providing shaded relaxation options. Nearby, a well-maintained lawn extends into the background.

Home in Plainfield

4.76 out of 5 average rating, 46 reviews

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 spacious, 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!

The spacious bedroom features a king bed with soft bedding, complemented by an accent chair and a lamp. Large windows offer a panoramic view of Chicago’s skyline, allowing natural light to fill the room while city details are visible outside.

Condo in Oak Lawn

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

A group of deer is observed grazing in a grassy area, surrounded by trees. The warm light of dusk casts a gentle glow over the scene, highlighting the soft contours of the landscape and the deer's slender forms.

Home in Bolingbrook

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.

Guest favorite

A large outdoor heated Jacuzzi is illuminated with soft blue lights, surrounded by cushioned headrests. Steam gently rises from the surface of the water, creating a relaxing ambiance for year-round enjoyment.

Guest suite in Homewood

4.98 out of 5 average rating, 88 reviews

Cozy Fun Game Room Suite & Hot Tub w/Yurt add on

Cozy intimate family/friendly fun space that includes: Large outdoor heated Jacuzzi opened year round 27' above ground heated pool (seasonally) until Oct. Pool and Air hockey table Arcade machine with 12 games Life Size Connect 4 Board games Basketball machine Electric fire place Queen size bed Queen Sofa pull out sleeper Gazebo with two twin beds (seasonal) Fresh Eggs with chickens seasonal Gas Grill-propane included Romantic Robe for 2 (in colder months must request) 1 dozen fresh eggs

Guest favorite

The interior of the event yurt features a high, domed ceiling with wooden beams. Tables are set with plates and utensils, surrounded by white chairs. Decorative elements include greenery and balloons, creating a festive atmosphere. A TV screen and a stage area are visible.

Yurt in Homewood

5 out of 5 average rating, 5 reviews

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

A spacious living area is highlighted by two navy blue sofas and a modern coffee table, with a wood piano situated against the wall. Large windows allow natural light to flow in, illuminating the soft carpeting and neutral wall colors.

Home in Glenwood

4.83 out of 5 average rating, 63 reviews

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!

An outdoor area features a spacious swimming pool surrounded by a wooden deck, offering ample space for relaxation. Lush trees provide privacy, with the home visible in the background. The deck shows a gentle slope leading toward the water, facilitating easy access to the pool.

Cabin in New Lenox

4.56 out of 5 average rating, 71 reviews

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

Top guest favorite

An above-ground pool is set amidst a lush green lawn, surrounded by trees. The deck area features steps leading up to the pool's edge, where colorful pool floats are visible. The peaceful outdoor space invites relaxation and enjoyment.

Yurt in Homewood

4.97 out of 5 average rating, 113 reviews

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 4 beds w/sofa sleeper Game Room w/bathroom 1 bed & sofa sleeper 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!

Home in Lockport

4.56 out of 5 average rating, 16 reviews

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.

The exterior of the home is displayed, featuring a welcoming entrance with a centered front door flanked by large windows. A well-maintained lawn and landscaped garden surround the home, with carefully arranged stones and shrubs leading to the entry. Trees offer shade in the yard.

Home in Orland Park

New place to stay

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.