Holiday 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 favourite

Home in Plainfield

4.94 out of 5 average rating, 77 reviews

Beautiful 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!

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.

Home in Plainfield

4.71 out of 5 average rating, 38 reviews

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

Discover the classic 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!

Home in Glenwood

4.81 out of 5 average rating, 58 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!

Guest favourite

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 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 must request)

Cabin in New Lenox

4.58 out of 5 average rating, 67 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 favourite

Yurt in Homewood

4.97 out of 5 average rating, 107 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

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!