Vacation rentals with a pool in Illinois

Highwood Haven/Indoor Pool/Hot Tub/Arcade

Unwind at Highwood Haven, an opulent McHenry getaway with a heated indoor pool and arcade. Savor culinary delights in our chef's kitchen, enjoy al fresco entertainment, and relax in sumptuous bedrooms. An hour from Chicago, it's ideal for luxury retreats and family fun. Revel in our nine-person hot tub, outdoor lounge with TV, and serene bedrooms. Make memories with both lively entertainment and tranquil moments, all within a luxurious setting. Your perfect destination for an upscale vacation.

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.

Cozy Garden Studio in Lake Linda Barn w/swimspa

This spacious studio in a shady forest is a clean newly remodeled open unit. A 50 in smart TV is provided. It has a comfy queen sized bed, a full sized fridge, sink and microwave and a new cozy gas stove/fireplace. Guests have access to a shared space with electric stove, washer and dryer and additional bathroom with large shower. You will be surrounded by scenery consisting of a 44 acre lake, gardens, and woodlands filled with animals and a vast variety of birds and a new swimspa to share.

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

*Fall Fun* *Hot tub-Fire-3 king beds-Game room*

Relax, unwind, & explore at this fall retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful fall 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 pit 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 adventure!

Detached, private guest house! a ms

Come stay in our carriage house turned guest house!, the property has a swimming pool available during swimming season, which is June thru September. a separate Hot Tub and new BBQ for your private use; please indicate if you intend to use the pool during your stay, we need an hours notice to remove the cover; the hot tub is always ready to use. You will be sure to enjoy the proximity to restaurants, shopping in Ottawa, parks such as Starved Rock, and a variety of festivals.

Lake Cabin in the Woods

🌲Looking for a relaxing getaway? Need a peaceful stopover on your Midwestern travels? Craving tranquility in a remote setting? Look no further—Lake Cabin in the Woods is your perfect retreat! Nestled about 60 miles from both Effingham, IL and Evansville, IN, our cabin offers the solitude you’re seeking without being too far from major highways. Located between Interstate 70 and Interstate 64, it’s a serene escape with easy access to wherever your journey leads.

Platypus Hills, Lake, Heated Pool, Hot tub,Firepit

This cozy 2-bedroom country house sits on 8 acres, sleeps and overlooks Clinton Lake with amazing views. We offer a hot tub, heated pool, kayaks, and 10 miles of hiking, hunting, and horse trails. The boat ramp is located at the end of the driveway. We are located 30 minutes between Bloomington & Champaign. All guests must be 18+. An additional $50 per person per night over 2. Pool open May-Sept. PLEASE READ THE ENTIRE LISTING TO ENSURE IT MEETS YOUR NEEDS.

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.