Holiday rentals with a pool in Oak Brook

The Metropolitan Retreat (Fitness Center • Sauna)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

2BR Downtown Elmhurst | Pool, Gym, Kings, Garage

A professionally managed 2-bed 2-bath apartment in downtown Elmhurst, providing the perfect balance of luxury and comfort for business travelers and families. Walk to the cafes, restaurants, and shops of downtown Elmhurst, nearby classy Oakbrook (8 mins), O'Hare airport (12 mins), and blocks to the Metra train station with easy access to downtown Chicago! Enjoy the pool, fitness center, garage parking, courtyard with firepits, pool table, and movie theater - convenience is at your fingertips!

Couples Getaway, Jacuzzi, Sauna, Pool is Open

Couples Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

Forest Park Oasis - Dog Friendly - Parks - the "L"

This newly remodeled two-bedroom home in Forest Park offers comfort and convenience, sleeping four with TVs in every room and a fully equipped kitchen. dog friendly, a dedicated workspace, hardwood floors throughout. Enjoy a formal dining room and electric fireplace. Located across from the park, pool, tennis courts, and Roos Recreation Center, it's just a 5-minute walk to the Harlem Blue Line Station, making downtown Chicago and airports easily accessible. Perfect for both work and leisure!

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.

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.

Music Hotspot 2nd Floor

Urban-style suite with Fiber Wi-Fi walking distance of 4 music venues. Crawling distance from Fitzgerald's music venues. 2 blocks from Autre Monde and other restarnats/stores. 3 blocks to the CTA Blue line & 6 blks CTA Green/Pink line. Close to parks, pools, the zoo, and Thatcher woods/river. Many amenities, including a unique landscape, a fire pit, a furnished patio, kool artwork, smoker, grills, two furnaces and more. Must be 25 years or older to book. Only get togethers - no parties!

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, and WIFI provided. Washer/Dryer available upon request. Pool is for registered guests only. Owners on site to assist if needed.

Spectacular 2BR Penthouse in the Loop | Roof Deck

This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed. The building has a pool and an amazing outdoor rooftop terrace with 360 degree views of the skyline and lake. This is the best location in the city!

Pond View, Washer Dryer, Non Smoking, Pet Free

Welcome to our cozy retreat! Fully furnished for affordability and convenience, our prime location near Downers Grove, Wheaton, Oakbrook, and Downtown Chicago ensures the perfect base for your stay. Enjoy free parking, washer-dryer, dishwasher, and amenities like linens, dishes, cookware, cable, wireless internet, queen-size bed, smart TV, and Hulu access. Little touches make guests feel truly at home, creating a delightful and memorable stay, whether for business or leisure.

Paradise with Pool & Games

Welcome to our 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 plenty of 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!

Hot tub. Heated Pool. In town location.

In ground pool!! (Seasonal) 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. Hot tub. Basketball hoop in driveway, bags set in yard, great summertime home! Walk to Marianos/CVS/Walgreens, near it all!