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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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, 77 reviews

Beautiful Spanish style Home (w/inground pool)

BethanyRating, 5 stars1 month ago

Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!

A sparkling saltwater swimming pool is featured, surrounded by a textured concrete deck. The pool's clear blue water reflects light, and the edge is lined with a decorative coping. Shade from nearby trees creates playful patterns on the pool's surface.

Home in Olympia Fields

4.56 out of 5 average rating, 43 reviews

Luxurious South Suburban Villa

LanceRating, 5 stars4 months ago

My team thanks you for your comfortable home, it is what the crew needs after a day working outside on a large solar field array. Whenever on an extended out of town work trip we like to stay at an Airbnb, a much better value than several rooms at hotels. Your home was roomy & comfortable, we enjoyed our stay and thank you for being a great host.

Home in Lemont

Celebrate at Hacjenda house

DianeRating, 5 stars2 months ago

I had such a great time at the Hacjenda House! I came here with my dog for a peaceful getaway and it was exactly that. Lena set up the fireplace inside for me and I was cozy all night. Plenty of firewood in their backyard. Super spacious and beautiful inside and out. Their tub upstairs is also so spacious for a bath. Lena was so kind by checking in on me throughout my stay. I didn’t want to leave. I definitely want to come back.

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, 86 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

Superhost

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

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

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

4.59 out of 5 average rating, 68 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, 109 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!

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Popular amenities for Will County rentals with a pool

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House rentals with a pool

Guest favorite

Home in Plainfield

4.94 out of 5 average rating, 77 reviews

Beautiful Spanish style Home (w/inground pool)

BethanyRating, 5 stars1 month ago

Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!

Home in Olympia Fields

4.56 out of 5 average rating, 43 reviews

Luxurious South Suburban Villa

LanceRating, 5 stars4 months ago

My team thanks you for your comfortable home, it is what the crew needs after a day working outside on a large solar field array. Whenever on an extended out of town work trip we like to stay at an Airbnb, a much better value than several rooms at hotels. Your home was roomy & comfortable, we enjoyed our stay and thank you for being a great host.

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

4.81 out of 5 average rating, 59 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

TiffanyRating, 5 stars1 month ago

I really enjoyed my stay. The owner was very helpful and quick to respond when I needed help. I definitely will keep this Airbnb in mind!

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

4.55 out of 5 average rating, 11 reviews

Hidden GEM OASIS in Chicagoland

BesjanaRating, 5 stars3 weeks ago

Everything was great! The place was just as imagined.

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

4.72 out of 5 average rating, 39 reviews

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

YajairaRating, 5 stars1 month ago

Such a great and responsive host for such a beautiful home! I definitely have to come back so I can enjoy the pool in the summer. It was a great home away from home. Spacius and well maintained. Would stay again!

Home in Lemont

Celebrate at Hacjenda house

DianeRating, 5 stars2 months ago

I had such a great time at the Hacjenda House! I came here with my dog for a peaceful getaway and it was exactly that. Lena set up the fireplace inside for me and I was cozy all night. Plenty of firewood in their backyard. Super spacious and beautiful inside and out. Their tub upstairs is also so spacious for a bath. Lena was so kind by checking in on me throughout my stay. I didn’t want to leave. I definitely want to come back.

Home in Bolingbrook

Peaceful backyard oasis. Unique!

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Vacation rentals with a pool in Will County

Top-rated rentals with a pool in Will County

Vacation rentals for every style

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House rentals with a pool

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