Vacation rentals with a pool in McHenry County

A cozy living area is highlighted by a gas fireplace and a large Smart TV mounted on the wall. A sliding glass door leads to a balcony with views of the green courtyard. Comfortable seating is arranged around a rustic coffee table that complements the relaxed atmosphere.

4.97 out of 5 average rating, 140 reviews

Cozy LG Retreat! King Bed! Fireplace! WiFi!

Your cozy & relaxing getaway begins in a newly redesigned condo with balcony (courtyard view), and is conveniently located between Lake Como and Lake Geneva in peaceful Interlaken Resort community! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, and more! The resort community is located by Lodge Geneva National (formerly The Ridge Hotel), which adds additional restaurants and available amenities at an additional charge. Walk to the

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, 211 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.

4.96 out of 5 average rating, 213 reviews

A serene outdoor area features a curved pool surrounded by a wooden deck and lush greenery. Potted flowers add color to the scene, while a shaded umbrella provides seating comfort. Tall trees offer natural privacy, enhancing the tranquil ambiance of the space.

Guest suite in Bartlett

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.

The image showcases a clear swimming pool surrounded by a concrete deck. A shallow area is indicated, with safety signage specifying '3 ft 0 in No Diving.' Poolside loungers and umbrellas provide shade, while pool steps offer easy access for swimmers.

4.87 out of 5 average rating, 101 reviews

Lake Geneva relaxation!

4 mi to Downtown Lake Geneva, WI. Rent kayaks on Lake Como. New pool and tennis courts, amazing wildlife. Snowboard, cross country ski, sled on hills during our amazing Wisconsin winters. Dine at The Ridge restaurant CRAFTED or just buy a bottle of wine from the guest store and watch the sunset. Quiet corner of the condominium complex. Completely furnished. Beautiful comfortable King size bed, kitchen, cook and eat in! Balcony overlooking peaceful grounds. Private entry, laundry in building.

Guest suite in Saint Charles

A spacious bedroom features a queen bed dressed in crisp white linens, accompanied by decorative pillows. Soft lighting is provided by a bedside lamp, while an accent rug adds warmth to the wood floor. A built-in shelf displays various decorative items.

5 out of 5 average rating, 292 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, 141 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.

4.91 out of 5 average rating, 144 reviews

Home in Highland Park

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!

4.84 out of 5 average rating, 388 reviews

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

"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

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.

4.78 out of 5 average rating, 181 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.

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, 155 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.

4.96 out of 5 average rating, 188 reviews

Relaxing Villa with Amazing Amenities!

Resort day passes included with booking! Hot tub, indoor and outdoor pool, outdoor bar and fire pit, sauna, the list goes on! Only five minutes from downtown Lake Geneva, this second floor condo offers the best of both worlds. Enjoy the laid back Lake Como attractions, or have a blast in Lake Geneva! This hidden gem is perfect from golfers (only 5 minutes from Geneva National) to families. Give us a try, and enjoy a discount on your second stay!

5 out of 5 average rating, 5 reviews

A fenced-in backyard features a landscaped yard with well-maintained grass surrounding a heated in-ground pool. The pool area includes a comfortable covered patio, providing shade with ample space for relaxation. Lush green trees and shrubs create a serene atmosphere.

Home in Crystal Lake

In Ground Pool, Full Ranch Home

In ground pool!! Rent this entire home, experienced hosts, near town, 5 min drive to Crystal Lake main beach OR Three Oaks Beach/Recreation. Clean, Updated Home, with fenced in yard and pet friendly. 4 beds total (3 bedrooms) and 1 full bath. Fully stocked kitchen with all cooking supplies that you need. Basketball hoop in driveway, bags set in yard, great summertime home! Walk to Marianos/CVS/Walgreens, near it all!

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Popular amenities for McHenry County rentals with a pool

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House rentals with a pool

An inviting swimming pool glistens under a bright sky, surrounded by lush greenery. The spacious patio features a covered area and lounge chairs, while the elegant home showcases large windows and a welcoming design, inviting relaxation in a serene outdoor setting.

4.94 out of 5 average rating, 17 reviews

Woodhaven, a Luxury Lake Geneva HotTub-Pool Estate

KarinRating, 5 stars1 month ago

Woodhaven was the perfect house for our women’s weekend away! The large living room and beautiful kitchen were perfect for our group of 10 but we were fortunate to have nice weather to be able to check out the downtown and spend most of our time outside on the patio. Even when the pool was still closed, we thoroughly enjoyed the backyard and patio space. Thanks for opening your home!

An aerial view of Elssys Ranch reveals a spacious estate surrounded by lush green fields and distant views of Lake Geneva. The well-maintained grounds feature a private pool and a sun deck, inviting relaxation amid the serene natural landscape.

5 out of 5 average rating, 13 reviews

Elssys Ranch 80 Acre Lake Geneva Retreat

AlexRating, 5 stars3 weeks ago

We had an amazing time at Nick’s property, and Nick was a great host from booking through the end of our stay. The property is incredible and a perfect location between Lake Geneva and Lake Delevan. We used the pool and fire pit every night, and the space comfortably fit 12 guys for our golf trip. We will definitely be looking to rent this property again in the future! Thanks for everything Nick

An outdoor seating area features a wooden picnic table with benches, surrounded by colorful autumn trees. A grill is covered nearby, and a glimpse of the pool can be seen in the background. The deck provides a spacious area for relaxation and gatherings.

5 out of 5 average rating, 33 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

DanielRating, 5 stars2 days ago

Sasha’s place was even better than expected. We all felt at home and it was very relaxing. We had plenty of room to accommodate all of the guests.

Two black Adirondack chairs and a small side table are positioned on a patio, overlooking a lush green landscape under a cloudy sky. The view encompasses rolling hills and tree foliage, providing a serene outdoor setting.

5 out of 5 average rating, 40 reviews

Newly Updated Modern Lake Condo

LaurenRating, 5 stars3 weeks ago

Loved this house! It was in a great location, a few mins away from town, walking distance to Lake Como and super easy to find and navigate. Everyone had a great time. Only drawback was a tiny kitchen for multiple people but the rest of the living areas were great!

4.82 out of 5 average rating, 74 reviews

Home in Wonder Lake

Great Kayaking, biking, hiking get away

RandallRating, 5 stars5 months ago

Check in was easy, and everything was as described. Julie’s place met our needs for a place to stay while visiting family. Her place is clean and well supplied. Lots of room which we didn’t use all of it. The fenced in area was nice to be able to let our dogs out.

A spacious outdoor pool area is presented, surrounded by a clean concrete deck. Several round tables with chairs are arranged around the pool, providing seating. Lush greenery and trees are visible in the background, contributing to a serene environment.

4.96 out of 5 average rating, 73 reviews

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

CynthiaRating, 5 stars1 month ago

We loved this place! Super fresh and clean, lots of natural light, great views, peaceful, private and super comfy beds. Perfect place for a couple of days to get our 22 year old out of the big city for some family time and renewal. Steven is a thoughtful host. Highly recommend!

4.89 out of 5 average rating, 63 reviews

An above ground pool with a diameter of 20 feet and a depth of 4 feet is surrounded by a grassy area and shaded by tall trees. A ladder provides access to the pool, and colorful floats are visible on the water's surface.

Home in Woodstock

Grand 1800s Victorian Gem: Updated/by Downtown

MikeRating, 5 stars2 days ago

Fantastic home, we all loved it and had such a great time! Deirdre was right on top of things, so friendly, it was a delight working with her. The home was beautiful, and looked just like the pictures. What a fantastic experience!

4.92 out of 5 average rating, 26 reviews

Home in Schaumburg

Schaumburg Oasis:Private Pool & Enchanted Garden

SarahRating, 5 stars4 days ago

We stayed here while our floors were being refinished and Marzena’s Oasis did not disappoint! You can tell she takes great pride in her listing; everything was as described and more. The home was very clean with plenty of linens, dishes, and kitchen/pantry supplies. My kids left more crumbs on the floor than usual during breakfast one day…I could not find a broom so I messaged Marzena. She dropped off a stick vacuum AND some delicious treats. Above and beyond to make us feel welcome and comfortable. Thank you for a home away from home!

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Condo rentals with a pool

A living room features a comfortable recliner and a smart TV positioned near a cozy fireplace. A large sliding glass door provides access to outdoor space, while the adjacent dining area is furnished with a wooden table and four chairs, complemented by a decorative rug.

5 out of 5 average rating, 3 reviews

Cozy Condo at Interlaken! Stay & Play on Lake Como

BrianRating, 5 stars2 weeks ago

Was a really nice little place with lots of beautiful tress surrounding it, and the lakes amazing. It was easy to find the place and just a great weekend overall

A private balcony offers stunning views of the tranquil lake at sunset, framed by lush greenery and a well-manicured lawn. The sky is painted with soft hues of orange and blue, reflecting on the calm water's surface.

5 out of 5 average rating, 8 reviews

Glass Vista: Modern 2BR Condo, Stunning Views

JasonRating, 5 stars3 months ago

This place was exactly what I was looking for a weekend with my girlfriend. It was super clean, premium environment, amazing view, and had all the things we would need for a weekend away from home!

The spacious living area is illuminated by natural light from large windows. A leather sofa is paired with an accent chair, while a round rug centers the space. A modern coffee table sits atop the rug, and a dining counter with two bar stools is positioned nearby.

5 out of 5 average rating, 18 reviews

Chic Condo in Lake Geneva.

ZoeRating, 5 stars1 week ago

I absolutely loved staying here! Morgan was extremely responsive and super friendly whenever she reached out! The condo was very clean and had everything we needed for a nice weekend trip! And, compared to a lot of other places in Lake Geneva, I think the condo was very reasonably priced. I would absolutely love to come back here :)

Condo in Fontana-on-Geneva Lake

A circular swimming pool is surrounded by a spacious patio with numerous lounge chairs. Lush greenery and trees frame the area, while nearby, a gazebo offers shaded seating. The multi-story condominium buildings in the background complete the inviting outdoor environment.

5 out of 5 average rating, 58 reviews

2 BD 2 BA Abbey Villa with Pool

GavinRating, 5 stars9 months ago

Great spot! The condo was clean, comfortable, and quiet. It was a short walk to the beach and restaurants. Mandy’s detailed directions and instructions made checking in a breeze. Our group of four had a fantastic time.

4.91 out of 5 average rating, 44 reviews

An outdoor pool area is enclosed by a black fence, surrounded by lounge chairs and umbrellas. Lush green grass leads to the area, with trees and a nearby building visible in the background. Clear blue skies create a bright and open atmosphere.

Condo in Geneva

Quaint, quiet condo minutes from Lake Geneva

AlenaRating, 5 stars1 month ago

Lively apartment, beautiful area, attentive host. Place was clean and spacious. We enjoyed our stay. Could hear the neighbors from upstairs. Didn’t bother me, but if you are not used to having neighbors it can be distracting.

A private balcony is showcased with two green chairs, offering a view of the shared outdoor pool below. Lush trees provide shade in the distance, and clear skies suggest a bright day. The railing provides safety while enjoying the surrounding scenery.

4.7 out of 5 average rating, 43 reviews

Poolside Lookout at the Cove Hotel |Downtown LG

DianaRating, 5 stars2 months ago

If you're looking for a relaxing, peaceful yet close to everything getaway....Samantha's place is it!! From the minute you walk into the Cove, you guide yourself straight into a restful oasis. Entering Samantha's place, I was amazed at how spacious it all was. From the very modern kitchen, all of the utensils and kitchen necessities to the wide tub in the bathroom and big bed in the bedroom, everything felt like home. Relaxing in the living room with a beautiful view to the outdoors and the balcony was enjoyable. I highly recommend Samantha's place for your next stay in Lake Geneva.

4.93 out of 5 average rating, 15 reviews

A cozy living area is presented, featuring a light blue sofa adorned with various throw pillows. A matching armchair sits nearby, and a coffee table with decorative items occupies the center. Natural light enters through a glass door, highlighting the warmth of the space.

Condo in Geneva

Cozy 2 Bedroom Condo - Lake Geneva

AnnaRating, 5 stars8 months ago

Nice comfortable space, and a good easy location. Walking distance from the lake. Space was even larger than it looked in the pictures, and clean and comfortable.