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

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.

Winter Fun! Hot tub-Fires in/outdoor-Game room!

Escape to our cozy luxe cabin in Galena Territory, the perfect retreat for fall! Start your mornings sipping coffee by the gas fireplace, then warm up each evening in the hot tub! Enjoy friendly competition with arcade games, board games, air hockey, and darts. With 10 amenity cards, you can access the owner’s club for swimming and exercise including indoor pickle ball-rackets and balls at the house! Experience relaxation and adventure in this tranquil haven—your unforgettable getaway awaits!

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.

Couples Getaway! Hot Tub, Lake, Fire Pit, Trails

Private entrance to a stunning master suite.A VERY unique property.Sliding suite door opens to screened in pool room. Hot tub all year overlooking my private lake. Pool closed Oct. 1st. Seating area & TV to watch while lounging & swimming. (2) Kayaks 4 you. Walking & bike trails. I am minutes from everything U want. Grill, have a fire in the fireplace&fire pit.Bring your fishing poles! Time 2 RELAX in privacy. When not traveling, I live in main part of home. You won’t see me. No extra guests.

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...

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

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.

Carbondale Pool House - Sauna, Hot Tub, Dogs OK

Rated in “Top 1%” by Airbnb, the Pool House is a separate cottage surrounded by gardens and swimming pool, with retro "Danish Modern" furniture, a gourmet kitchen and plush beds. We have recently added a Finnish Sauna and Japanese Ofuro Soaking Tub. We accept well behaved dogs for a fee of $35 a night. We allow only guests and friends of the Pool House on the grounds, gardens or pool. Hosts are Jane, anthropologist and D. a retired photojournalist for the New York Times.

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.

Aspen House - A Secluded Getaway In Nature

Relax with your loved ones at the peaceful Aspen House. A Miner's Cottage nestled in a beautiful stand of aspen trees = a quiet retreat just for you! The property is surrounded by protected wooded green space with the Taylor Run trail adjacent on the northwest side. The Owners Club, pools & lake are accessible by hiking/ 5 minute drive. Enjoy bird watching, fishing, hiking and picnicking without driving anywhere!