Holiday rentals with a pool in Naperville

4.9 out of 5 average rating, 528 reviews

Apartment in Uptown

Whole Flat in Private Club. Walk to L, Dining & Shows

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

4.94 out of 5 average rating, 77 reviews

Home in Plainfield

Beautiful Spanish style Home (w/inground pool)

Experience a mix of old and new at this recently renovated Spanish style villa. Casa Dra’eh – less than an hour from Chicago! Staying for business or leisure, this stylish retreat offers the perfect blend of sophistication and comfort. Relax on the private rooftop balcony overlooking the backyard , featuring a pool and veranda ideal for dining. Cook in the chef’s kitchen or unwind in modern Spanish decor. With Chicago just a short drive away, enjoy the best of both worlds. Book your stay today!

4.96 out of 5 average rating, 213 reviews

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.

Apartment in Logan Square

4.97 out of 5 average rating, 114 reviews

Fun & cozy getaway w/POOL/game room/FREE parking

Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

Guest suite in Saint Charles

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.

4.97 out of 5 average rating, 116 reviews

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Sky Terrace and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Harmony of Evanston features granite countertops in the kitchens, 9 ft ceilings, and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, BBQ and picnic area and beautiful landscaping. In the warmer months, Guests can enjoy the Clark Street Beach & Lighthouse

4.95 out of 5 average rating, 22 reviews

Home in Schaumburg

Paradise 4BR w/ Pool & Games

Welcome to our family-friendly 4BR home. Enjoy lazy summer days by our sparkling pool, where you can soak up the sun and cool off with refreshing dips. Our well-appointed kitchen is ideal for preparing delicious meals together, and the cozy living areas provide ample space for relaxation and bonding. With nearby attractions and easy access to downtown Chicago, our home offers the perfect balance of suburban serenity and urban excitement. We can't wait to host you for an unforgettable stay!

Apartment in Near North Side

4.9 out of 5 average rating, 101 reviews

50th Floor Mag Mile Studio

This Downtown Chicago unit is towering 50 stories above the city, with floor to ceiling windows in the living areas. This unit gives you the ultimate in Luxury urban living. It's all about the views and location. The city unfolds before you with amazing sunsets; nowhere in Chicago can you stay with views like these. The building provides the very best in amenities. A state of the art fitness center, Outdoor pool, Outdoor kitchens, business center, are available to our guests.

4.93 out of 5 average rating, 27 reviews

Home in Schaumburg

Schaumburg Oasis:Private Pool & Enchanted Garden

Welcome to our uniquely located home!- a serene escape in the heart of Schaumburg. We offer a tranquil garden adorned with fairy lights, custom mushroom decor, and a cozy pergola—perfect for evening relaxation. a short walk to a grocery store, pharmacy, café, and cleaners, everything you need is within reach. Enjoy the spacious, fully fenced backyard with a hidden garden, private swimming pool, propane fire pit, fresh herb gardens, and one-of-a-kind vintage interior design,

4.86 out of 5 average rating, 22 reviews

Home in West Chicago

Cozy & Relax Escape

You are booking a Cozy, Modern, and SPACIOUS Basement Apartment with a Private Entrance, and a large open-concept Guest Suite! Located in one of West Chicago incorporated quiet neighborhoods. Host occupies the separate 1st floor. You’ve your own private entrance & space. No SHARING!! Why Share if you can have your own private space for a reasonable rate. Pool is available for rent.. Max 15 people allowed! Inground heated pool with deep & shallow end. Pool size 16x22.

4.97 out of 5 average rating, 109 reviews

Yurt in Homewood

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 4 beds w/sofa sleeper Game Room w/bathroom 1 bed & sofa sleeper Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Breakfast included is 1 dozen fresh eggs!

4.9 out of 5 average rating, 20 reviews

Home in Elgin

Entire Home in Elgin with Pool!

Welcome to our spacious family home in Elgin, featuring a large backyard patio perfect for outdoor relaxation and entertainment. Inside, enjoy a cozy yet modern space with ample room for everyone. The highlight of the home is a fully equipped theatre room in the basement, ideal for movie nights and unwinding after a day of exploring. Perfect for families or groups, our home offers comfort and fun in a quiet neighborhood! Pool open on June 1st

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House rentals with a pool

Home in Montgomery

5 out of 5 average rating, 4 reviews

5 bdrm/2.5 bth/Fenced Yard/Quiet St /Pet friendly

JessRating, 5 stars6 days ago

Jennifer & Tony were fantastic hosts; personable, quick replies, and proactive. The house was amazing, even better than the pictures. The backyard was huge and perfect to have the kids play. The beds were so comfy. Perfect house to be home base when visiting the area. I definitely recommend this place and the hosts. Looking forward to next year's visit "back home".

Home in Glen Ellyn

4.83 out of 5 average rating, 12 reviews

Pardizes Suites

CrystalRating, 5 stars2 weeks ago

I was speechless when I walked in her house it was beyond beautiful nothing was out of place at all when I say she had everything you can think of to accommodate us all she had all the toiletries you could think of the kitchen was stocked with all kind of seasonings dishes she even stocked breakfast sausages she put balloons out she really out done herself she went above and beyond it was plenty of games there the rooms were beautiful the beds were so comfortable I didn’t want to get up it was the best airbnb I ever stayed in we were all blown away by how beautiful and clean and neat it was Lisa is a very great hostess you all make sure to book with her she is great

Top Guest favourite

Home in Schererville

4.95 out of 5 average rating, 57 reviews

Cozy house in Schererville

AlishaRating, 5 stars2 weeks ago

Kate's house was cute, comfortable and the beds were fantastic. Also, we loved all the beautiful rose bushes...great landscaping! Definitely recommend!

5 out of 5 average rating, 11 reviews

Home in Munster

Munster hide away

ChristopherRating, 5 stars5 months ago

Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Home in Plainfield

4.73 out of 5 average rating, 40 reviews

30 mins to CHI| 3 Kings| BBQ Grill| Spacious| Pool

CourtneyRating, 5 stars2 weeks ago

We had an absolutely wonderful stay at Sarah’s Farmhouse. The house was clean, comfortable, and had everything we needed for a perfect getaway. Both Sarah and Maxwell were very responsive and helpful. We highly recommend this Airbnb!

4.92 out of 5 average rating, 52 reviews

Home in Bloomingdale

Now Open: Heated Pool with Entire House

AmyRating, 5 stars1 day ago

Really great place to stay, super responsive host! The pool was pretty great and so was the hot tub! Great location too, lots of stores, restaurants around, and parks like the Busse Woods (it’s huge and lots of walking paths)!

4.88 out of 5 average rating, 56 reviews

Home in Lincoln Park

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars1 week ago

Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!

PatriciaRating, 5 stars1 week ago

Home in Skokie

New place to stay

Luxury fenced in modern ranch

It was a chaotic start to our vacation stemming off my daughter's graduation from Northwestern; however, Jennifer immediately took the stress off my shoulders and welcomed our family to a fabulous stay at her home. Words cannot express how grateful my family is and without Jennifer's help it would not have been as successfull. I highly recommend staying at any of her properties. She will go above and beyond to make sure you're stay is wonderful!

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Condo rentals with a pool

4.92 out of 5 average rating, 63 reviews

Condo in Downers Grove

Upscale, Washer Dryer, Smoke Free, Pet Free,

ChidoRating, 5 stars3 months ago

I really loved the place—it was cozy, soundproof, and felt just like home. It had a warm, inviting atmosphere and a great sense of comfort. Plus, the neighborhood felt very safe, which made our stay even better.

4.96 out of 5 average rating, 98 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

PhillipRating, 5 stars1 month ago

Great Stay - Nice unit and facility. Michelle was very responsive and helpful during my stay. Would stay in one of her properties again when I’m back in town.

4.95 out of 5 average rating, 108 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

StaciRating, 5 stars3 weeks ago

Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.

Condo in The Loop

4.45 out of 5 average rating, 11 reviews

voco: Balcony & City View

AmitRating, 5 stars2 weeks ago

gorgeous views and very nice condominium. great balcony and very safe. The elevators were super fast. Even though the actual location is different than the one mentioned in listing, it still wasn't disappointing. There is enough space for a small family or a couple.

Condo in Lombard

4.84 out of 5 average rating, 56 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

LelandRating, 5 stars5 months ago

Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.

Condo in Magnificent Mile

4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars25 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

4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars3 months 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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️