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

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

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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

Guest favourite

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, 8 reviews

Event Space Glamping Yurt, Cabin & RV sleeps 25

Look no further! This unique experience on 2 acres of land will leave you and your guest full of memories. Host your event & enjoy a glamping sleepover. Glamour + Camping=Glamping! Opened May 1-Nov 1 Swimming/2 hot tubs Sauna/Volley/ Basketball court 4 grills and hibachi-30' Event yurt-20' Safari yurt-Cabin w/bathroom RV w/bathroom-Game room Suite w/bathroom- Tent-Screened in Gazebo. Spacious Event Space Yurt & Pavilion also includes: Seating, Cold Buffet t, Throne Chairs, tables & more!

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.

Home in Lemont

New place to stay

hacjenda - where memories are made

family reunion, birthday party, or just any gathering to celebrate the special occasion, hacienda is a place to stay. beautifully located on the hill, with ample amount of parking, large living room finished in cedar,wood burning fireplace, 3bedrooms 2bathrooms,patio with a large table, grill,swimming pool( open june- August)bonfire area for late night talks. open for events up to 30 people. prices vary depending on number of people, event and few other factors. look forward to have you !

Tiny homes in Crete

Luxury Indoor Glamping! 38 minutes from Chicago

This is not your traditional camping experience! This is one of 3 different luxury trailer styles. Hosts are allowed to have up to 20 guests to entertain until quiet hours at 11:30 pm. Additional fees may apply for additional guests over sleeping capacity. Check out our photos to see everything we have to offer! From our indoor mechanical bull, outdoor theater screen, pool table, outdoor club, playground, basketball, volleyball & horses you'll definitely be entertained. Please message us

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

4.84 out of 5 average rating, 70 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

4.49 out of 5 average rating, 83 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

Guest favourite

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

4.96 out of 5 average rating, 101 reviews

Game-room lower-level suite/hot tub w/add on Yurt

Activities includes: PS5 Disc w/TV Xbox Series X w/TV Outdoor heated Jacuzzi 27' above ground pool Pool and Air hockey table Arcade machine with 12 games Life Size Connect 4 Board games Basketball machine Electric fire place Queen & full size beds Full size 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) Event Yurt add on $225 up to 25 additional guest

Top guest favourite

The camper is shown with its door open, revealing easy access. Two padded camp chairs face a smokeless fire pit, which emanates a vibrant flame. An outdoor griddle is positioned nearby on a patterned rug, offering a cozy atmosphere for gatherings.

Camper/RV in Plainfield

5 out of 5 average rating, 10 reviews

The Amanita

Welcome to The Amanita, a unique camper nestled in our spacious backyard, offering a rare retreat with over an acre of land in downtown Plainfield. This space offers privacy and a serene atmosphere with high-speed Wi-Fi, a kitchen, outdoor griddle, a family-friendly environment, and chickens! Experience the tranquility of nature and the excitement of downtown, including the Warehouse 109 district. Ideal for singles, couples, and small families, the Amanita awaits your visit!

Superhost

A sparkling pool is framed by a spacious patio, featuring lounge chairs and tables for relaxation. Nearby, a playground is visible, along with a covered seating area and a Blackstone grill, all surrounded by greenery and a serene setting.

Home in Plainfield

4.77 out of 5 average rating, 53 reviews

30 mins to CHI|3 Kings|BBQ Grill|TV| Spacious

Discover the Farmhouse on Main! 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!

A single-story house is set against a backdrop of trees, featuring a stone facade and a sloped roof. A winding driveway leads to a two-car garage on the right. Lush green grass surrounds the home, contributing to a serene environment.

Home in Lockport

4.39 out of 5 average rating, 23 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

4.73 out of 5 average rating, 30 reviews

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.