Vacation rentals with a pool in Naperville

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Top-rated rentals with a pool in Naperville

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Guest favorite

Apartment in Uptown

4.9 out of 5 average rating, 519 reviews

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”

Guest favorite

Home in Plainfield

4.93 out of 5 average rating, 75 reviews

Relaxing 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!

Guest favorite

Guest suite in Bartlett

4.96 out of 5 average rating, 209 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.

Top guest favorite

Apartment in Logan Square

4.97 out of 5 average rating, 104 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.

Top guest favorite

Guest suite in Saint Charles

5 out of 5 average rating, 288 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.

Guest favorite

Home in Schaumburg

4.96 out of 5 average rating, 27 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

Freshly updated house with in-ground POOL! Minutes to Woodfield mall and restaurants in Schaumburg. One of the only houses with private pool in the area. LOCATION: 35 min to downtown Chicago, 20 min to O'Hare airport, 20 min to Rosemont convention area MASTER BEDROOM extra large for primary guest(s). Unpack and stay awhile with a large walk in closet. Luxurious attached master bathroom with double sink and large walk in shower with bench. Pool is open from May until the end of September.

Guest favorite

Home in Schaumburg

4.95 out of 5 average rating, 20 reviews

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!

Guest favorite

Home in Elgin

4.87 out of 5 average rating, 15 reviews

$10 Cleaning Fee Promo! - Home in Elgin

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! **$10.00 Cleaning Fee Promo if you book by May 31st**

Guest favorite

Home in West Chicago

4.94 out of 5 average rating, 16 reviews

Cozy & Relax Escape

Nice and clean place to stay in West Chicago and call it your home during your personal or business trip. You'll enjoy the accessibility to all nearby restaurants, grocery stores and shopping mall. Close to major highways. You’ve your own private entrance & space. No SHARING!! Why Share if you can have your own private space for a reasonable rate. It is our priority to create an experience for you that is cozy, comfortable, and relaxing! Hope to see you soon!

Guest favorite

Home in Schaumburg

4.91 out of 5 average rating, 22 reviews

Schaumburg Oasis with a Pool and Hidden Garden

Welcome to our uniquely located home! Just 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, fire pit, and fresh herb garden. Our house stands out with its one-of-a-kind vintage interior design, featuring the Marilyn's Glamour Suite, Elvis' Rock 'n' Rest, Einstein's E=mc2 Escape, and the famous Coca-Cola Pop & Play Lounge.

Guest favorite

Home in Glen Ellyn

4.98 out of 5 average rating, 60 reviews

Luxury Home: Heated Pool, Hot Tub, Firepit, 1 Acre

**Heated Saltwater Pool & Hot Tub Now Open!** Welcome to our exquisitely renovated luxury estate home, nestled on 1.25 acres. This stunning property offers an exceptional vacation experience with its array of amenities perfect for friends and family gatherings. The expansive backyard features a private heated saltwater pool and spa, fire pit, yard games, oversized dining table, and grill—everything you need for endless outdoor entertainment and relaxation.

Top guest favorite

Home in Bloomingdale

4.94 out of 5 average rating, 48 reviews

Whole House With Hot Tub And Spacious Bedrooms

Welcome to our spacious 4-bedroom home! Enjoy lounging in the airy living area or cooking in the fully equipped kitchen. With a master bedroom featuring a king bed and en-suite, a second bedroom with a king bed, a third with a queen, and an office space for the fourth bedroom, plenty of room. Plus, unwind with a game of pool on the basement's pool table. High-speed internet keeps you connected. Hot Tub open! Swimming Pool closed until May.