Holiday rentals with a pool in Cook County

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.

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.

Couples Retreat | 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.

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.

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!

Game Room Suite with hot tub & Event Yurt up to 25

Activities includes: PS5 Disc w/TV Xbox Series X w/TV Outdoor heated Jacuzzi 27' above ground pool Pool and Air hockey table Arcade machine with 12 games Life Size Connect 4 Board games Basketball machine Electric fire place Queen & full size beds Full size sofa pull out sleeper Gazebo with two twin beds (seasonal) Fresh Eggs with chickens seasonal Gas Grill-propane included Romantic Robe for 2 (in colder months must request) Event Yurt add on $225 up to 25 additional guest

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!

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.

50th Floor Mag Mile Views, Balcony, Pool, Gym

The Penthouses at Grand Plaza PH#12: Towering 50 stories above Downtown Chicago, this luxury unit features floor-to-ceiling windows and breathtaking skyline views. Enjoy sunsets, unmatched location, and true urban living. Walk Score of 100 with a grocery store in the building. Amenities include a fitness center, outdoor pool, kitchens, and business center. The city is at your feet—experience Chicago in style.

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

Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 2 roll-out beds welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.

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.

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

Welcome to your home away from home! Whether you're visiting for business, a family vacation, or a weekend getaway, this home offers the perfect blend of comfort, convenience, and relaxation. Everything is thoughtfully set up to ensure a smooth and enjoyable stay. Book your stay today and make yourself at home!