Vacation rentals with a pool in McHenry County

5 out of 5 average rating, 72 reviews

An indoor heated pool reflects vibrant blue water, surrounded by colorful lounge chairs. Nearby, an arcade room features classic pinball machines and video game consoles, set against polished wooden flooring. Large windows allow natural light to fill the space, creating a bright and energetic atmosphere.

Home in Janesville

*Family Retreat* *Indoor Pool* *Arcade*

The Pool House is the perfect family retreat for any group that wants quality time with quality amenities. Come enjoy everything our home has to offer and make all those wonderful memories with the ones you love. The indoor heated pool is perfect for that private party experience that can be followed up with the fully loaded arcade room. Enjoy the pinball machines and great classic arcade games then go off to the full size Golden Tee and Buck Hunter and see if you can get the new high score.

A patio area features multiple seating options and a glass door leading into the condo. Lush greenery and colorful flowers border the concrete walkway, providing a serene outdoor setting. A second-level balcony is visible above, adding depth to the outdoor space.

4.98 out of 5 average rating, 206 reviews

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

Superhost

An outdoor space features a gazebo and comfortable seating, framed by vibrant flowers. The heated above-ground pool is visible, surrounded by a wooden deck. Lush greenery serves as a backdrop, creating a serene setting enhanced by soft evening light.

Home in Carol Stream

4.42 out of 5 average rating, 24 reviews

Amazing Summer Pool Awaits You!

Vacation, Staycation or Business, you will love your stay at this beautiful paradise with heated pool and tri-level entertainment deck equipped with grill and outside seating and gazebo! Semi-secluded backyard, walking distance to bike path, playground, skate park, walking trails, restaurants and even the gym! Relax on the magnificent deck while watching the sunset This home is pet free and smoke free. Pool is available May-Sept. WiFi is available throughout and Smart TV in the family room.

Guest suite in Saint Charles

A clear blue pool is showcased, surrounded by a smooth concrete patio and a white picket fence. Adjacent tennis courts are visible in the background, along with a grassy area that enhances the outdoor space.

5 out of 5 average rating, 287 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

An outdoor pool area is surrounded by well-maintained landscaping, featuring several lounge chairs and tables. A patio with umbrellas provides shaded seating options. The pool is enclosed by a fence, with a clear view of greenery in the background. An adjacent gazebo offers additional space for relaxation.

4.96 out of 5 average rating, 138 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

Enjoy your stay at our family's Serene Lake condo with outdoor pool. NEWLY UPDATED Stylish and comfortable with amenities for any family to feel at home. Part of Interlaken community and set on Lake Como, we are surrounded by peaceful woods and often seen wild life, yet a quick drive into down town Lake Geneva, William's Bay and Fontana. Enjoy golfing, dining, water sports and all the region has to offer, then cozy up and relax with a view. NO RV, BOAT or TRAILER parking is allowed.

Condo in Fontana-on-Geneva Lake

A dining area features a round wooden table surrounded by four wicker chairs. A brick accent wall and green paneling provide texture, while natural light enhances the space. A doorway in the background leads to additional areas of the villa.

5 out of 5 average rating, 12 reviews

Luxurious Condo Experience at Lakeside Villa |Pool

Vacation memories await at this 2 bedroom, 2 full bathroom Abbey Villa at the West end of Geneva Lake. A true standout within the association, Lakeside Villa has been finished with thought and detail to deliver a luxurious condo experience. Walk-able to everything Fontana has to offer, including restaurants, boat rentals, and the beach- not to mention, the fantastic Abbey Villa pool that is just steps away! Book today to discover why guests return to the Abbey Villas year-after-year!

The spacious living room features a large sectional sofa in neutral tones, focused around a gas fireplace. A flat-screen smart TV is mounted above the brick hearth. Sliding glass doors open to the outdoor patio, allowing natural light to fill the space.

4.98 out of 5 average rating, 142 reviews

Cozy Lake Geneva Retreat | Amenities | WiFi

Discover Blue Lakes Escape, a newly-redecorated condo, steps away from Lake Como. Relax in the spacious great room with a smart TV, fireplace, desk area & access to quaint patio. Sit outside with a coffee, a good book, or a delicious BBQ. Enjoy free access to the shared amenities, including an outdoor pool, sports courts, & walking trails. Lake Como – 6 min walk Lodge Geneva National – 6 min walk Downtown – 8 min drive Book For Lasting Memories In Lake Geneva—See Details Below!

Superhost

A serene outdoor area features a clear swimming pool surrounded by a spacious stone patio. Lush green trees provide natural shade, and several lounge chairs are arranged around the pool, offering ample seating. A gazebo and additional seating are visible in the background.

Chalet in Ingleside

4.84 out of 5 average rating, 387 reviews

"A" Frame Brandenburg Lake

Getaway to a cozy 1 bedroom w/loft for 2, up to 6 people. Full kitchen 1.5 bath all season getaway. There is a piano as well. A tranquil home steps from a private lake. Oak and Pine surround you plus a stone fireplace, it feels like the North Woods. The A Frame guest house shares a 5 acre compound ( total 20 Acres) with the owners residence and caretaker cottage. The Volo Bog 800ft away. No hot tub Nov - May. Swimming pool usually June-October often cool to use in early June.

Superhost

An open living area features hardwood floors and a white brick fireplace. Comfortable red leather sofas are arranged around a white coffee table. A dining area is visible, adjacent to the kitchen, with a wooden table and chairs. Natural light filters through large windows.

Condo in Fontana-on-Geneva Lake

4.78 out of 5 average rating, 180 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

Enjoy a fun romantic get away or time away to connect with family and friends in Fontana-on-Geneva. Condo is an open concept kitchen, dining, and family room with fireplace. Enjoy the outdoors while relaxing on the screened in porch attached to the great room. First floor Master Bedroom has a semi-private full bath. Downstairs has a large second bedroom and full bath. There is also an office area which has a large double bed and a common area with TV and 2 extra twin beds.

4.98 out of 5 average rating, 51 reviews

A spacious indoor heated pool is visible, featuring clear blue water. Sturdy stairs lead into the pool, and a lounge chair is positioned nearby. The pool area is brightened by overhead lighting, with a staircase and doors leading to an adjacent space.

Home in Grayslake

Family-sized Indoor Heated Pool & Movie Theater!

**HUGE INDOOR HEATED POOL**THEATER**SLEEPS UP TO 18 MAX** Set on a private and quiet property, this home boasts a 24/7/365 huge heated indoor in-ground pool attached to the house that is yours to use exclusively. The house has a private movie theater and fully stocked gourmet kitchen! Our occupancy is 18 max visiting or staying. Bring your well-behaved, house-trained dog to join you for no additional fee! **30 day rental available** You will not be disappointed!

A breathtaking view of the sunset over Lake Como is framed by large glass doors. The patio features comfortable seating, adorned with potted plants, while the tranquil lake and lush greenery create a serene backdrop.

4.97 out of 5 average rating, 146 reviews

Magnificent waterfront views & cozy fireplace

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

A view from the balcony captures a well-maintained lawn with a cloudy sky backdrop. A tennis court is visible in the foreground, while trees and a body of water create a serene atmosphere in the background.