Vacation rentals with a pool in Will County

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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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Home in Plainfield

4.81 out of 5 average rating, 36 reviews

30 mins to CHI*3 Kings*Fireplace*2 Desks*BBQ Grill

Experience the tranquility of this 2,400ft² charming turn-of-the-century farmhouse. Brimming with character, its serene outdoor space features a state-of-the-art flat top grill and elegant granite bar countertops for delightful meals. Relax in the cozy seating area, complete with a warm outdoor fire table, or take a refreshing dip in the inviting pool! ★ 5 minutes to downtown Plainfield ★ Quick 20 minute drive to Naperville ★ Just a 30 minute drive into Chicago Come enjoy Plainfield with us!

Home in Olympia Fields

4.53 out of 5 average rating, 40 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.

Guest favorite

Yurt in Homewood

4.97 out of 5 average rating, 101 reviews

Glamping Yurt&RV;Game Room;Pool;Sauna;Hotub Courts

Glamping Experience to the next level now open all year. Spring/Summer & Fall/Winter Mini Resort Includes: RV - Spring/Summer 20' Safari Yurt - Spring/Summer 30' Event Yurt w/beds all year Outdoor wooden Barrel-Sauna 27' above ground swimming pool 6-7 Person outdoor hot-tub Gazebo twin beds, TV Game Room w/bathroom, pool/air hockey table Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Spring/Summer May - Oct sleeps 14 Fall/Winter - Nov - Apr sleeps 8-10

Rental unit in Park Forest

5 out of 5 average rating, 4 reviews

Quaint Park Forest Apartment - Near Golf Courses!

Whether you're attending a concert at the Credit Union 1 Amphitheatre, visiting the Tinley Park Convention Center, or teeing off at surrounding golf courses, this convenient 1-bedroom, 1-bathroom vacation rental is your perfect home base! Take advantage of the outdoor community pool in the summer, or walk to the park and play a match of tennis. Staying inside? This charming Park Forest apartment also features a well-stocked kitchen, an in-unit laundry area, and a Smart TV for movie nights!

Home in Glenwood

4.79 out of 5 average rating, 53 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 gazebo, 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!

Cabin in New Lenox

4.56 out of 5 average rating, 57 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

Camper/RV in Plainfield

5 out of 5 average rating, 9 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!

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Condo in Oak Lawn

5 out of 5 average rating, 4 reviews

2flr Big-3bedrms 2bath with Garage Parking

Comfortable 3 bedroom, 2 bath Condo. The whole group will enjoy easy access to everything from this centrally located-Big Condo. New Furniture, Full size Sofa bed, 2 workstations, Washer/dryer in basement. Great Views. Garage Parking and Driveway. Everything you need for your stay. Restaurants, hospitals, Amazon Fresh. Bus stops, Metra train station. Close to Dan Ryan expressway I-90/94. Easy access to Expressways to head Downtown, Southside, South and West Suburbs.

Guest favorite

Guest suite in Homewood

4.97 out of 5 average rating, 72 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 Spring/Summer/Fall Gas Grill-propane included Romantic Robe for 2 (ask to include)

Guest favorite

Condo in Oak Lawn

5 out of 5 average rating, 7 reviews

1flr Spacious-3Bedrooms/2 Bath w Garage Parking

Very Comfortable, 1st flr- Big Condo. Great Location. King size, Queen, 2twin beds, 1.5 bath. 3 T.Vs, Wifi. Garage parking. Midway Airport, Metra Train, easy access to Expressways I90/94 to downtown 20mins, Toll Road I-294. Walk to Walgreens, Jewel, Target, Andy’s Custard, Portillo's Rest., Amazon Fresh, Christ/Children’s, OSF Hospital. No pets, No smoking. If guests can't verify Identity I will decline reservation.