Vacation rentals with a pool in Illinois

4.9 out of 5 average rating, 20 reviews

A brightly lit neon sign for 'Log Cabin' is positioned in front of a lively street scene, showcasing quaint storefronts and a bustling atmosphere during twilight. In the lower segment, a foosball table is visible within a well-lit game room, featuring arcade machines and hardwood flooring.

Townhouse in Galena

Townhome - Indoor Pool, Arcade, Hiking, Skiing

KendallRating, 5 stars3 weeks ago

Hannah was wonderful to work with! We had questions using the lock & she responded right away and was able to help. When we had questions about the temperature she was there right away to answer. The space is adorable and had everything- from baby items to games! I highly recommend!!

4.89 out of 5 average rating, 121 reviews

Home in Putnam

The Beach House

Christopher CharlesRating, 5 stars7 months ago

Amazing house, great views, great communication with owner, and overall great experience! It does technically fit 10 people but that’s assuming that 8 people have to share a bed with someone else which was less than ideal for our group but could be totally someone else could be looking for. Definitely 5/5 stars and would not change a thing about our experience!

An outdoor swimming pool is featured with a gentle slope, surrounded by lounge chairs. A water slide is visible next to a shaded pavilion. Green planters with foliage add a natural touch to the area, enhancing the inviting atmosphere of the recreational space.

4.87 out of 5 average rating, 123 reviews

Sweet Escape~Galena Territory~Hot Tub~Pool Table

MiaRating, 5 stars3 weeks ago

We stayed here for a friends reunion with a group of 10, and it was absolutely perfect! The house had plenty of space, lots of bedrooms, and everything was super clean. The neighborhood was quiet and peaceful—exactly what we were hoping for. We especially loved all the amenities, the hot tub, pool table, and cozy fireplace made our stay extra fun and relaxing. We did run into a little hiccup with the self check-in, but one quick call to Jennifer and she helped us out quickly and efficiently. It was a great deal for such an amazing place, and we’ll definitely book again if we’re back in Galena with a big group. Highly recommend!

5 out of 5 average rating, 8 reviews

An inviting inground heated pool is surrounded by a spacious deck featuring comfortable lounge chairs in blue and black tones. Lush greenery serves as a backdrop, contributing to a serene outdoor atmosphere. A sloped entry to the pool accommodates easy access.

Home in Rockford

5 Acres of Solitude and Fun!

MariahRating, 5 stars1 month ago

I love love loved Dawns BEAUTIFUL home the pictures are good but you have to see it in person! Very spacious big enough for me and 10 of my relatives and it was very clean, it felt like home! Big tvs in every room, cabinet full of board and card games, outside activities to do like bags or basketball…. I can go on and on about this place! I didn’t want to leave lol we will definitely be booking again!

4.96 out of 5 average rating, 194 reviews

The swimming pool is surrounded by a white fence, framed by trees and greenery. A covered patio area sits nearby, providing shaded seating options. The clear water reflects the sky and the surrounding landscape, creating a calm and inviting setting.

Guesthouse in Lebanon

Pool, Hot Tub and Dog Paradise

GretaRating, 5 stars5 months ago

We enjoyed our stay at Amy’s Pool House! It was perfect for our trip visiting family during thanksgiving. Close to everything we needed and easy to find and access. The house was well stocked, esp plenty of towels! It was perfect for our dog too. He loved their yard and it was perfectly quiet for him. There is plenty of space and its comfy. We really enjoyed using the tv, and the hot tub! You could see the stars at night. :) We found the pool house a bit chilly at times and the bed was not our preference but overall we really enjoyed our stay! Amy was also very responsive and kind! We would come back here to stay again! :)

4.99 out of 5 average rating, 249 reviews

A serene view of the Pool House from the swimming pool, showcasing a welcoming porch adorned with colorful flowers. The pool's clear blue water reflects the bright sunlight, and vibrant, large-colored balls float gracefully on the surface.

Guesthouse in Carbondale

Carbondale Pool House - Sauna, Hot Tub, Dogs OK

KellyRating, 5 stars1 month ago

If you’re looking for a peaceful, family and dog friendly, design focused place to stay, this is your spot. The garden was incredible with spring ephemerals and flowering cherry blossoms blowing in the wind. This was the perfect home base for exploring wineries and the Shawnee National Forest. The loft was the perfect spot to set up our young toddler’s pack-n-play, though fair warning that there is little sound insulation from the kitchen and main living to the upstairs while your little one is sleeping. We wouldn’t hesitate to book this glorious pool house again with our babe in tow! 10/10

The modern home is set against a backdrop of trees, with a flat grassy area in the foreground. The structure features large windows and a prominent stone chimney, offering ample outdoor seating on the deck. The natural surroundings create a peaceful atmosphere.

4.9 out of 5 average rating, 119 reviews

Modern Home w/Amazing Views, Hot Tub, Game Room

RobinRating, 5 stars3 weeks ago

We had such a great time! We took the whole family (10 people) and there was plenty of room. The basement was great for keeping the kids entertained. They were wore out from playing video games, air hockey, basketball, and hot rubbing. The area has beautiful views, and feels very private even though there are houses close buy - which we prefer just in case we would need help. We all wished we could have stayed longer! We highly recommend and will definitely be back!

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!

Annika SusanRating, 5 stars2 weeks ago

We really enjoyed our family weekend. The house had plenty of space for everyone. The pool added so much fun and we really appreciated how secure the door to the pool was. We traveled with a 7 year old and it was comforting that he could not get into the pool room without an adult. The theatre in the basement was great and made the UFC fight even more fun. We chose to cook all our meals at the house. We found everything we needed in the fully loaded kitchen. We also took advantage of the fire pit in the private backyard. My husband and I enjoyed a nice walk around the neighborhood. We felt very comfortable and safe. Also the coffee shop “something’s brewing” is close by and a must stop. We appreciated plenty of towels and blankets. Thank you namestay for hosting us! Great house for a staycation!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Illinois rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.75 out of 5 average rating, 4 reviews

A two-story house with a black and white exterior features a covered front porch with seating. The entrance is flanked by green shrubs and trees displaying autumn foliage, enhancing the home's inviting presence. A concrete pathway leads to the front steps.

Home in Beardstown

Nostalgia on 5th St

CynthiaRating, 5 stars3 months ago

We would love to stay here again. I appreciate your flexibility—a wonderful host.

4.94 out of 5 average rating, 48 reviews

A clear swimming pool is surrounded by lush greenery and a wooden deck. Lounge chairs are placed nearby, and a colorful inflatable pool float rests on the water's surface. Sunlight reflects off the pool, enhancing its inviting blue color.

Home in Bloomingdale

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars2 weeks ago

Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again

4.94 out of 5 average rating, 146 reviews

Awesome Lodge in Galena Territory

RoseanneRating, 5 stars4 days ago

Beautiful home, with awesome view of golf course. Plenty of space to move about , large deck to sit and relax. Alex was very accommodating on check in time and was very responsive. Gave us detailed instructions for checking in and checking out. Lighting was labeled so there was no guessing on which switches controlled which lighting which was very helpful

4.88 out of 5 average rating, 60 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

BeckyRating, 5 stars1 week ago

Deidre is an amazing host. She goes above and beyond for each guest. We always appreciate her welcoming us into her home and her attentive and responsiveness to our requests. Highly recommend!

4.95 out of 5 average rating, 38 reviews

Home in Washington

A Luxe Pool & Hot Tub Retreat~ Westgate Oasis

GraceRating, 5 stars2 months ago

Absolutely wonderful experience from beginning to end. Well-maintained, relaxing, soothing, and just all around beautiful. Hope to visit again.

4.93 out of 5 average rating, 15 reviews

An in-ground pool is surrounded by a white fence, with stairs leading into the clear water. Comfortable lounge chairs are positioned nearby, offering a place to relax. Lush greenery and a spacious yard extend beyond the pool, creating an open view of the countryside.

Home in Geneseo

Charming Geneseo Farmhouse

DonaldRating, 5 stars1 week ago

Beautiful clean home with great character. The host was very professional and responsive. We will definitely come back in the summer months and enjoy the pool house/pool.

4.93 out of 5 average rating, 29 reviews

The backyard features a circular swimming pool surrounded by a red wooden deck. A spacious two-story house sits in the background, with a patio area containing an umbrella over a table. Lush greenery provides a natural border, enhancing the outdoor space.

Home in Lyndon

Waterfront,hotTB,swimming pl,pickleball,billiard

WalterRating, 5 stars7 months ago

This house suited us perfectly! Nemira had it ready for us on short notice which was very much appreciated!

A two-story home is set within a green landscape, featuring a dark exterior with light trim. A covered porch offers seating and welcomes guests. The sloping lawn leads to a manicured pathway, while trees provide a natural backdrop. A screened area is visible on the right.

4.82 out of 5 average rating, 293 reviews

Galena Retreat - Eagle Ridge Territories

TracyRating, 5 stars5 months ago

Really enjoyed our stay! Clean and comfortable and felt right at home. Thanks Sandy!

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Condo rentals with a pool

4.92 out of 5 average rating, 13 reviews

The aerial view captures a recreational facility featuring a large outdoor pool and a smaller children’s pool, both surrounded by lounge chairs and blue umbrellas. Lush greenery and hills provide a natural backdrop, while pathways lead to various amenities and buildings.

Condo in Galena

Beautiful Lake Galena Views - Walk to Stonedrift S

KerryRating, 5 stars7 months ago

We just returned from a 3-night stay at this incredible Airbnb, and I can't recommend it enough! Our group of four had an absolute blast – it truly exceeded all our expectations. First and foremost, the cleanliness was top-notch. You could tell the hosts take pride in maintaining a space that makes guests feel welcome and comfortable from the moment they step inside. The amenities were thoughtfully curated – we didn't want for a single thing during our stay. From the kitchen to the bedrooms to the living areas, every detail was considered to create a home-away-from-home atmosphere. But what really made our stay special was the peaceful surroundings. The quiet, relaxing environment was the perfect antidote to our busy lives. We left feeling refreshed and rejuvenated. If you're looking for a stress-free, comfortable getaway... look no further. We can't wait to come back and create more amazing memories.

5 out of 5 average rating, 35 reviews

A welcoming living area is filled with natural light, featuring a circular dining table surrounded by four upholstered chairs. A comfortable seating arrangement is positioned nearby, complemented by a ceiling fan and a flat-screen TV mounted on the wall. A modern fireplace adds warmth to the space.

Condo in Champaign

Modern Feel Condo 2 bd /2 bath 1 car garage

אליעדRating, 5 stars1 month ago

Damon's place was perfect for us! Really nice and cozy and had all we needed. Damon was super nice and helpful. Highly recommend

A bright living space is showcased, featuring large windows that invite natural light. A stone fireplace is positioned against the wall, complemented by a wooden mantel with artwork above. A television stands on a stand nearby, and a cozy seating area is arranged for relaxation.

Condo in Jo Daviess County

4.83 out of 5 average rating, 6 reviews

Lake Links Loft in Galena, IL

DavidRating, 5 stars3 months ago

Our family had a fantastic job at Dan's place. The location is great - close enough to the Eagle Ridge Inn and Owners Club, but very private location with a beautiful view of the lake. The unit had everything we need and was much larger than the pictures made it seem. Galena had great shopping and restaurants. Galena Territory Owners Club indoor pool was perfect for the kids. I'd recommend staying here anytime we make it back to Galena Territory!

Condo in Jo Daviess County

An entryway is shown, featuring a covered structure with a wooden floor and gently sloping roof. Snow is visible on the ground and rooftops, while shrubs and bare trees surround the area, indicating a serene and wintry atmosphere.

4.8 out of 5 average rating, 5 reviews

Long Bay Point Unit C5

AlyxRating, 5 stars5 months ago

My husband and I stayed here for 4 nights. It's a 10 min drive from downtown Galena in a quiet wooded area with paved trails that you can take to the nearby amenities. The place was clean, quiet, and the bathtub was amazing! The gym and indoor/outdoor pool are very nice but about 1.5 miles from the condo which wasn't stated anywhere (or at least not anywhere we saw) and was a little disappointing but overall wasn't a huge deal. The restaurant is a short walk through the trails or you can drive to it. It's right next door. Also, the initial message you get after booking with the rules and asking to email them out of the app was a little daunting and not normal for Airbnb bookings. It just had a less "homey" experience that you expect from Airbnb. It made me slightly nervous but after everything I would certainly stay here again.

An outdoor pool area features a clear, blue body of water surrounded by lounge chairs. Lush greenery is placed in large planters along the perimeter, with a backdrop of modern high-rise buildings and a cloudy sky.

Condo in Chicago

4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars23 months ago

Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.

Condo in Elk Grove Village

The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.

4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars1 month ago

I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️