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Vacation rentals with a pool in McHenry County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in McHenry County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Villa in McHenry

4.95 out of 5 average rating, 20 reviews

Fabulous Cabin

WELCOME TO WATERFRONT LOG-SIDED HOME! ARTISAN CRAFTMANSHIP HOME OFFERS A BACKYARD OASIS SITUATED , NESTLED ON A PRIVATE POND, Heated POOL(closed till April 1st), GAZEBO, FIRE PIT, FISHING! 4 BEDROOMS AND 4.5 BATHS The homes sits on the highest point in the neighborhood and has stunning views in the front & backyard! Enjoy the mornings sitting on your front porch. The main floor is completed by an office, den and laundry room! The finished walkout basement in with a custom built bar, game area

Condo in Lake Geneva

4.98 out of 5 average rating, 196 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.

Guest suite in Bartlett

4.96 out of 5 average rating, 207 reviews

Cozy & Spacious Suite in Quiet Neighborhood

This 950 sq. ft. guest suite is in a quiet, upscale neighborhood, less than 1/2 mile from Bartlett Hills Golf Club and a mile from Metra Train Station. 50 min. train ride to downtown Chicago. 10 min. walk to downtown Bartlett. A private entrance makes check-in easy and convenient, while offering privacy during your stay. Full kitchen, accessible bathroom, WIFI, and cable provided. Washer/Dryer available upon request. Pool is for registered guests only. Owners on site to assist if needed.

Guest suite in St. Charles

5 out of 5 average rating, 274 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.

Home in Highland Park

4.91 out of 5 average rating, 140 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Chalet in Ingleside

4.84 out of 5 average rating, 383 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.

Condo in Fontana-on-Geneva Lake

4.78 out of 5 average rating, 179 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.

Condo in Lake Geneva

4.95 out of 5 average rating, 128 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

Enjoy your stay at our family's Serene Lake condo with outdoor pool. 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 Lake Geneva

4.98 out of 5 average rating, 120 reviews

Magnificient views in a Lakefront condo, 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. Your stay promises a perfect balance of peaceful relaxation and recreational activities creating unforgettable memories in this beautiful Wisconsin setting.

Condo in Lake Geneva

4.97 out of 5 average rating, 106 reviews

Lake Geneva Retreat! King Bed! Fireplace! WiFi!

Your cozy getaway begins in a newly remodeled, ground level condo with patio, conveniently located between Lake Como and Lake Geneva in Interlaken Resort! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, and more! The resort community is located by The Ridge Hotel, which adds additional restaurants and available amenities at an additional charge. Many local areas to explore & visit will await your arrival.

Home in Wonder Lake

4.82 out of 5 average rating, 71 reviews

Great Kayaking, biking, hiking get away

Great get away for family and friends. This home has plenty of rooms to accommodate large groups --a long with great pricing for small groups. Pet friendly - There is a fenced in back yard with a patio, fire-pit and grilling—you need to supply the wood and charcoal. Jacuzzi tub and fireplaces inside the house to relax to also. Special girls get away to add massage/spa event at the house. Reach out for details Pet fee is refundable ask for details

Condo in Lake Geneva

4.97 out of 5 average rating, 76 reviews

LG Quaint Condo on Lakeshore Dr.

1+1 condo off Lakeshore Blvd, just minutes from downtown LG. Home is the perfect balance of quaint meets modern touch. Wake to a full coffee and tea station, cook in your own full kitchen. Walk to the lake, take a boat out just a few blocks away, or enjoy a scenic drive downtown. Experience the quiet and original charm of Lake Geneva without sacrificing the convenience of being close to DT LG. Book alone or with another condo in the same building.

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Popular amenities for McHenry County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Lake Geneva

4.93 out of 5 average rating, 14 reviews

Woodhaven, a Luxury Lake Geneva HotTub-Pool Estate

Home in Milton

4.84 out of 5 average rating, 208 reviews

Tree Top House with mini indoor pool and sauna

Home in Lake Geneva

5 out of 5 average rating, 4 reviews

Luxury 80 Acre Private Lake Geneva Estate

Home in Delavan

5 out of 5 average rating, 21 reviews

Winter Specials ~ Family friendly & dogs welcome!

Home in Lake Geneva

5 out of 5 average rating, 30 reviews

Newly Updated Modern Lake Condo

Home in Bensenville

5 out of 5 average rating, 16 reviews

New! Arcade+Sauna+Slots+Karaoke+more by O’Hare

Home in Lake Geneva

4.95 out of 5 average rating, 59 reviews

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

Home in Woodstock

4.87 out of 5 average rating, 52 reviews

Grand 1800s Victorian Gem: Updated/by Downtown

Condo rentals with a pool

Condo in Fontana-on-Geneva Lake

5 out of 5 average rating, 58 reviews

2 BD 2 BA Abbey Villa with Pool

Condo in Elk Grove Village

4.95 out of 5 average rating, 74 reviews

Just remodeled apartment close to airport and mall

Condo in Geneva

4.93 out of 5 average rating, 40 reviews

Quaint, quiet condo minutes from Lake Geneva

Condo in Lake Geneva

4.84 out of 5 average rating, 68 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

Condo in Lake Geneva

4.87 out of 5 average rating, 98 reviews

Lake Geneva relaxation!

Condo in Lake Geneva

4.63 out of 5 average rating, 269 reviews

Flexible rental In Lake Geneva Area

Condo in Lake Geneva

4.92 out of 5 average rating, 26 reviews

Best Location in Lake Geneva!

Condo in Lake Geneva

4.8 out of 5 average rating, 30 reviews

Historic Hayloft Lodge |Ziplining |Pumpkin Patch

Destinations to explore