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 hallway features arched openings along white walls, accented by warm lighting that highlights the dark wood flooring. Dark doors are positioned at either end, providing a clean and sophisticated look.

Home in Plainfield

4.93 out of 5 average rating, 75 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!

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

Relax and enjoy the luxury of this beautiful Chicagoland villa. Exquisite interior finishes with black bamboo flooring, large comfy couches, several large flat-screen TVs. A fully stocked kitchen with high end appliances two microwaves one with air fryer. Enjoy the large outdoor space with a heated saltwater swimming pool, quality poolside outdoor furniture, large Treager pellet grill. Home also has plenty of grassy area in the front and back, with a paved basketball court on the side.

The bedroom features a spacious bed adorned with soft linens and decorative pillows. Large windows allow natural light to fill the room, complemented by elegant sheer curtains. A distinctive floral accent wall adds character, and a bedside lamp provides warm illumination.

Home in Plainfield

4.7 out of 5 average rating, 37 reviews

30 mins to CHI +3 Kings + Fireplace+W/D+Workspace

Discover the classic charm of this 2,400ft² turn-of-the-century farmhouse, where character meets comfort. Relax in the serene outdoor space featuring a flat-top grill and granite bar countertops. Inside, unwind in the cozy seating areas, gather with loved ones around the large dining table, and take advantage of the spacious, fully equipped kitchen. ★ 5 minutes to downtown Plainfield ★ Quick 20 minute drive to Naperville ★ Just a 30 minute drive into Chicago Come enjoy Plainfield with us!

Guest favorite

A view of the large above-ground heated pool is presented, surrounded by a spacious patio. A dining table with chairs is visible on a wooden deck, adorned with a vase and decorative items, while greenery defines the serene outdoor setting.

Guest suite in Homewood

4.98 out of 5 average rating, 85 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 table Air hockey table Arcade machine with 12 games Life Size Connect 4 Board games Basketball machine Indoor 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 available must request)

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

4.8 out of 5 average rating, 56 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

4.58 out of 5 average rating, 66 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 favorite

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!

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, 106 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

Superhost

A circular pool is surrounded by a wooden deck, featuring steps for entry. Lush greenery and trees provide a natural backdrop, enhancing the serene atmosphere. Two lounge chairs are positioned nearby, inviting relaxation in the private outdoor space.

Farm stay in Monee

4.85 out of 5 average rating, 40 reviews

Rock Creek Farm 5BD with Pool

Welcome to Rock Creek Farm! Discover our private oasis with 5 bedrooms, 2.5 baths, a pool, fire pit, hammock, and trails on 40 acres of land. Just 25 minutes from Cedar Lake and 40 minutes from downtown Chicago, it's the perfect place to relax and disconnect. Pool open Memorial Day to Labor Day. Book now!