Holiday rentals with a pool in Illinois

The Pool House 1-Bedroom Home with Hot Tub & Pool

Soak in the hot tub or relax poolside at The Pool House! Its country setting is perfect for a relaxing stay, romantic getaway, business trip or spending time with your family. Enjoy a full kitchen, electric fireplace and spacious bedroom. *No parties allowed *No pets allowed *No smoking allowed *No photo shoots allowed Maximum of 5 guests We DO NOT have a TV, but you're welcome to bring one. We DO have WIFI. **Military discount is available. Please message us first by clicking "Contact host

Haven Estates_: Cozy Barn, Hot Spa & heated Pool

Enjoy a peaceful countryside retreat at this charming Barndominium set on 6.5 private acres, accommodating up to 8 guests This spacious getaway features an 18' x 36' private pool with a hot spa and a solar-heated pool room for year-round relaxation. The Great Room offers open-concept living with comfortable seating, recreation space, and four sleeper sofas. The cozy bedroom includes a king-size bed, while the fully equipped chef’s kitchen boasts an oversized island & a stove with an air fryer.

Private, Galena Log Cabin

This custom log cabin is the perfect getaway for friends & family seeking the solitude of the Galena Territory and fine dining and shops just 10 minutes away on Galena's Main Street. Each of the 3-levels offers an owner's suite with bath. Cozy up to 2 fireplaces, grill on the deck, or make 'smores at the firepit. The cabin has high speed, fiber internet and the lower-level walkout features a 55” flat screen TV. Guests can access swimming pools & pool tables at the Owner's Club 7 minutes away.

Family Fall! Hot Tub•Fire In/Out•Game Room•3 Kings

Relax, unwind, & explore at this Fall Retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and fall/winter adventure!

Embers of Murphysboro

Escape to the beauty of Embers of Murphysboro.  The sprawling landscapes and cabin with high end amenities have everything to offer for a weekend getaway or larger gathering.  Sucumb to the beauty of nature around you that will awaken your inner senses and relax your mind.  Nestled upon a  26 acre property the cabin will astound you with picturesque landscapes and a lodging infused with both character and luxury.  Explore local wineries, hiking trails, fishing,  boating , dining and more...

Secluded and Stunning Lodge - Hot Tub, Hiking

Hi, hello there, welcome! Bring your friends and family and get ready to relax. Our spacious lodge is the perfect getaway for those looking for some peace and privacy. Located adjacent to Ferne Clyffe State Park, you can lace up your hiking boots and wander straight onto the trails. The Southern Illinois Wine Trail and multiple state parks are a short drive away, but you'll soon find yourself back in the privacy of our 28 acre retreat. Come and enjoy all that our unique cabin has to offer!

Ottawa Oasis. Billiards. Pool. Pet Friendly!

Welcome to the Ottawa Oasis! 🐕🏠 This pet friendly house comprises a downstairs unit with an in-law suite above. 🥾 Just a 1 mile walk to downtown Ottawa and short drive to starved rock. 🏊‍♂️ 🥽 Come back home after a long day hiking and cool off in the private inground pool. 🍳🍽 Cook dinner in either of the two kitchens in the house. 🎱🕹Enjoy family game nights in the enclosed porch, playing pool, arcade games (contains 14 different games), ax throwing, and giant connect 4!

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

Pool, Arcade, Hot Tub and more @16th and Aldeen

Do you want to be the Hero? Hero spouse, hero golf buddy, even Guitar hero?! You can be that and more at our hole-in-one nestled at the end of a quiet street right by a top 50 rated public golf course. Get in a round then head back to the hot tub to soothe that putting shoulder while the kids play in the pool. Then head inside to the arcade to play guitar hero till you win that Grammy you always wanted. Top it off with a family movie night! Pet fee $50/night per dog max 2 dogs

Golden Meadows Escape: A Luxurious Country Retreat

"This home is flawless! From the serene, private location to the abundant amenities, our trip was perfect. My kids especially loved the theater room and gaming console." – Sadie Golden Meadows Escape offers the perfect blend of tranquility and entertainment, with easy access to everything Galena has to offer. This beautifully designed home rests on a spacious 2+ acre lot, ensuring endless peace and family fun. "A taste of luxury with all the charm of the countryside" – Matt

Cozy Cottage on Mumford

Fully renovated, cozy, and with ample amenities. Centrally located in Urbana, Illinois. Just 2 miles from the University of Illinois campus, 10 minutes away from downtown champaign, and a short walk away from multiple parks. Designed for entertaining with an open concept living area, 70" tv, and a saltwater pool out back. Access to many games, bags set, and bbq grill out back. Pool will be open Memorial day to Labor day. House also has an electric car charger free to use.

Private Cabin w/Pool on Lake Centralia, sleeps 12.

Welcome to Deer Creek Cabin on Lake Centralia. Relax with the whole family at this peaceful private retreat. A large deck surrounds the pool for all your family fun. Fishing and kayaking are just steps away. Enjoy your morning coffee in the screened-in porch overlooking a quiet cove of the beautiful lake. It is common to see deer, geese, ducks, turtles, and blue heron. As night falls, cozy up around the fire pit to make more family memories.