Vacation rentals with a pool in Schaumburg

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.

Grand 1800s Victorian Gem: Updated/by Downtown

Step back in time with this Victorian, pet friendly, home featuring original pocket doors, gorgeous inlaid floors, & sparkling leaded glass windows. You will feel right at home with the comfort of the updated kitchen and baths with tons of space for all sized groups. This home is just three blocks from downtown Woodstock where you can dine, shop, & visit the famous opera house. Don't forget to visit the many scenes the movie Groundhog Day was filmed at throughout town and toast to world peace!

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.

Naperville Family Fun! Pool, Pickleball, Kids Room

A premium, resort-like experience in a professionally managed 2-bedroom / 2-bathroom property, providing the perfect balance of luxury and comfort for business travelers and families. Enjoy the pool, pickleball court, kids' play room, courtyard with firepits, fitness center, pool table, and sauna - convenience is at your fingertips! Explore nearby downtown Naperville (8 mins), classy Oakbrook Terrace, the beautiful Morton Arboretum, and downtown Chicago, a short drive or train ride away!

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!

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!

Private, Pet Friendly. Hot Tub! Fireplace. In Town

Private ranch home with in-ground pool (seasonal) + hot tub! Enjoy this clean, updated Crystal Lake home just 5 minutes from Main Beach and Three Oaks Recreation Area. Features 3 bedrooms, 4 beds, 1 full bath, a fenced pet-friendly yard, indoor fireplace, fully stocked kitchen, laundry room, basketball hoop, lawn games, and backyard TV in a covered patio! Walk to Mariano’s, CVS and Walgreens, with downtown, restaurants, beaches and more just minutes away!

Fun 5BR 4.5BA, Pool, Hot Tub, Game Rm, Near O’Hare

Welcome to this spacious and comfortable home in Wood Dale, ideally located near O’Hare Airport and Downtown Chicago. Perfect for families and groups, this home features multiple bedrooms, a fully equipped kitchen, free parking, and relaxing living spaces. Enjoy easy access to shopping, restaurants, parks, and nearby attractions. Whether you're visiting for business or leisure, this home offers comfort, convenience, and great value for your stay.

Backyard Paradise/ Private Pool + Peaceful Stay

Welcome to your peaceful retreat near Chicago, surrounded by a beautiful garden perfect for relaxing, morning coffee, or unwinding by the private pool. Step inside and enjoy a cozy Friends-inspired living room full of charm and comfort. Entire two-story duplex is yours—private garden, pool, and gazebo. Complete privacy guaranteed, no shared spaces of any kind. A truly unique stay you won’t find anywhere else—book your escape today!

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Modern-Luxe experience at the Unity of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 3 bedrooms, 2 full baths, 1 roll-out bed welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown. This unit is all about bring a family together in UNITY!

Just remodeled apartment close to airport and mall

This is just remodeled first floor 1 bedroom apartment that has everything you need for a comfortable stay. Conveniently located 14 min from O'hare airport and 10 min from Woodfield mall that has to offer variety of stores and huge amount of restaurants. All kitchenware for cooking your meals, board games for fun, pool to relax on summer so you get most out of your stay here.