Some info is shown in its original language. Translate

Home rentals with a pool near Chicago River Walk

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool near Chicago River Walk

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top Guest favourite
A rooftop pool area features a long, inviting pool bordered by lounge chairs in various colors. Sunlit trees are visible nearby, and the backdrop consists of modern high-rise buildings, creating a vibrant urban atmosphere.
Apartment in Chicago
4.93 out of 5 average rating, 108 reviews

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.

Guest favourite
An inviting outdoor space features a sleek pool with a gentle water feature, surrounded by neat landscaping. The modern two-story structure rises in the background, complemented by a black umbrella positioned near the water's edge, creating a serene atmosphere for relaxation.
Guesthouse in Chicago
4.86 out of 5 average rating, 35 reviews

Andersonville Luxe Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape. The pool and spa are heated heated through 12/31.

Superhost
Apartment in Chicago
4.85 out of 5 average rating, 80 reviews

Luxury Designer Penthouse 3804 | Pool | Gold Coast

NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. Sitting 38 stories in the sky, your 3 bedroom/2 bathroom penthouse offers some of the best views in all of Chicago. The highly secure building includes elevator, rooftop pool, full gym, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 28 reviews

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Top Guest favourite
An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.
Apartment in Chicago
4.98 out of 5 average rating, 152 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.

Guest favourite
A bright living area features large windows that offer city views, enhanced by natural light. Comfortable gray seating is arranged on a patterned rug, complemented by modern decor and greenery. A flat-screen TV is mounted on the wall, alongside a stylish coffee table.
Apartment in Chicago
4.82 out of 5 average rating, 339 reviews

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!

Superhost
Apartment in Chicago
4.72 out of 5 average rating, 39 reviews

Luxury Smart Home for Corporate Travelers

Luxury smart high-rise designed for corporate stays and business travelers. This fully furnished unit features seamless smart home controls, high-speed WiFi, and a dedicated workspace for productivity and comfort. Located in the heart of downtown, steps from the river, dining, and nightlife. Ideal for professionals in town for training, projects, or short-term assignments. Please note: this unit is located directly on the north side of the river front in the Streeterville area.

Superhost
Apartment in Chicago
4.79 out of 5 average rating, 161 reviews

Level ◆ Brand New Luxe One Bedroom

Designed with you in mind, our One Bedroom Suites range from 560 – 698 sq ft of spacious living space boasting fully-equipped kitchen, comfortable living area, spa-inspired bathroom, bedroom with king bed and open-air balcony. Perfect for couples and corporate travelers alike, all suites also feature in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling. Welcome to the suite life.

Guest favourite
Apartment in Chicago
4.86 out of 5 average rating, 78 reviews

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

Experience luxury 50 stories above Downtown Chicago in this modern convertible 1BR apt. Enjoy breathtaking sunset & city views from floor-to-ceiling windows & a private balcony. Perfect for 2 guests, this space offers resort-style amenities including a pool, fitness center & more. With a grocery store in the building & Lake Michigan nearby, convenience is at your doorstep. Ideal for a romantic getaway or a solo urban adventure.

Guest favourite
An open-concept living space is showcased, featuring modern kitchen appliances, a dining table with seating for six, and a comfortable sofa. Large windows allow natural light to fill the area, providing views of the outdoor landscape.
Condo in Evanston
4.96 out of 5 average rating, 116 reviews

"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!

Superhost
A modern living area is displayed, featuring large windows that provide city views. A gray sectional sofa complements a circular coffee table on a light area rug. A wall-mounted flat-screen television is present, alongside a cleanly designed console. A spacious bed is visible in the background.
Apartment in Chicago
4.82 out of 5 average rating, 51 reviews

Level Junior Two Bedroom Suite | Fulton Market

Two bedroom, two bathroom suite featuring a king bed, queen bed, and sofa bed. Maximum occupancy is 4. Enjoy access to over 32,000 sq ft of unrivaled lifestyle amenities, including a seasonal outdoor pool, a relaxing hot tub, and a state-of-the-art fitness center. Take in stunning views of the Chicago skyline from our Cloud Lounge, grill meals at the BBQ stations, and enjoy movie or game nights in the media room.

Guest favourite
The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.
Condo in Elk Grove Village
4.93 out of 5 average rating, 110 reviews

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 in summer and some snacks to get most out of your stay here.

Popular amenities for rentals with a pool near Chicago River Walk

Quick stats about rentals with a pool near Chicago River Walk

  • Total holiday rentals

    Explore 420 holiday rentals in Chicago River Walk

  • Nightly prices starting at

    Chicago River Walk holiday rentals start at $100 NZD per night before taxes and fees

  • Verified guest reviews

    Over 5,060 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 250 rentals that welcome pets

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

  • Wi-Fi availability

    420 of Chicago River Walk holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chicago River Walk rentals

  • 4.7 Average rating

    Chicago River Walk stays receive an average rating of 4.7 out of 5 from guests