Holiday rentals with a pool in Tinley Park

Stylish Corner 2 Bedroom in the Heart of Chicago |

[NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2nd rooftop remains open and available for guests to use.] This stylish corner apartment is in a perfect location with fabulous city views in multiple directions. It's a bright and spacious two bedroom, two bathroom apartment with an additional sofa bed, ideal for families, business travelers, or couples traveling together. The building has a pool and an amazing outdoor rooftop terrace w

Professional's Playground (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.

Couples Getaway, Jacuzzi, Sauna, Pool

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.

Beachfront- Lake Michigan-Hot Tub-Heated Pool

Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

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.

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Central location near Grant Park, Art Institute, The Bean, Soldier Field, & more! ✅ 1 Free parking pass ✅ FAST WIFI ✅ En-suite Laundry ✅ The Lake & Park are only 2 blocks away ✅ KING beds ✅ Private Rooftop Deck w/ stunning views ✅ Amenity Floor (Gym, Pool, Lounge, Doggy Park) ✅ 1 block from Red "L" subway

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!

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is mandatory. Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental.

"Joy of Evanston" 1BDR, KING EXEC Suite, 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. Joy 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, outdoor pool, BBQ and picnic area and beautiful landscaping. Guests can enjoy the Clark Street Beach & Lighthouse

Bayless Dune Lodge at West Beach - Indiana Dunes!

Bayless Dune Lodge at West Beach is a gorgeous, Lodge-themed home in Miller Beach, Indiana, a scenic community surrounded by the Indiana Dunes National Park! A short walk to one of the finest white sand beaches on Lake Michigan, the Lodge sits on nearly half an acre of land nestled into the "Bayless Dunes Nature Preserve." The property boasts a heated, in-ground swimming pool, pool-side lounge area, two outdoor dining areas, two spa-quality bathrooms and more!