
Vacation rentals with a pool in Evanston
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Evanston

Total vacation rentals
Explore 10 vacation rentals in Evanston

Nightly prices starting at
Evanston vacation rentals start at R 325 ZAR per night before taxes and fees

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Over 1,040 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Evanston vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Evanston rentals

4.9 Average rating
Evanston stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in Evanston
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Whole Flat in Private Club. Walk to L, Dining & Shows
Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”
4.9 out of 5 average rating, 600 reviews
Highrise Hideout (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.
4.92 out of 5 average rating, 121 reviews
Luxury Designer Penthouse 3803 | 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!
4.88 out of 5 average rating, 59 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.
4.98 out of 5 average rating, 172 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!
4.81 out of 5 average rating, 359 reviews
Cozy studio near Michigan lake
Welcome to your cozy urban retreat by the shores of Lake Michigan! Nestled in the lively neighborhood near Loyola Park, this charming studio apartment offers a delightful blend of modern comfort and vibrant city living. The decor is welcoming and will create a pleasant atmosphere. Kitchen provides everything you need to prepare meals! Enjoy the sandy shores of Lake Michigan. Our convenient location offers access to public transportation, grocery stores, a variety of dining options!
4.74 out of 5 average rating, 93 reviews
West Loop Loft|Sleeps 4, Parking, Pool, & Rooftops
Stay in a striking West Loop loft for 4 with free onsite parking—a rare Chicago perk. Framed by an oversized arched window, this stylish 1BR features a queen memory-foam bed, rollout trundle, sleeper sofa, full kitchen, central A/C and in-unit laundry. Resort-style amenities are all under one roof: indoor pool, gym, sauna, steam room, basketball court, running track, coworking lounge, café, bar, plus skyline rooftops with grills. Ideal for couples, families and business travelers.
5.0 out of 5 average rating, 3 reviews
Luxury fenced in modern ranch
Escape to the stunning remodeled, exquisite upscale mid-century modern luxury ranch near downtown Skokie three blocks from the subway, Skokie waterpark and Evanston golf club-and by staying at the stunning property, you are in the heart of Skokie at the edge of downtown with easy access to almost everything! Relax and unwind in my fenced in yard or perhaps use the pizza maker to help make a pizza with the kids! For worship needs, I am 2 blocks away from Church and Temple.
4.86 out of 5 average rating, 7 reviews
Harmony of Evanston 1 BDR Exec Suite w/pool & Gym
Eco-Friendly, modern, sleek, condo with modern finishes and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Harmony 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, BBQ and picnic area and beautiful landscaping. In the warmer months, Guests can enjoy the Clark Street Beach & Lighthouse
4.96 out of 5 average rating, 147 reviews
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.
4.9 out of 5 average rating, 143 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 on summer so you get most out of your stay here.
4.92 out of 5 average rating, 127 reviews
Riverfront Views - Smart Home - Simple Check In
Luxury smart home in a high-rise designed for corporate stays and business travelers. This fully furnished unit features seamless smart home controls, high-speed WiFi, and designed for 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.
5.0 out of 5 average rating, 17 reviewsPopular amenities for Evanston rentals with a pool
House rentals with a pool

Riverwoods Nature Retreat
5.0 out of 5 average rating, 3 reviews
Pardizes Suites
4.85 out of 5 average rating, 27 reviews
Rosemont 4BD2BA house with Pool
5.0 out of 5 average rating, 28 reviews
Luxury Loft with Private Pool and Movie Theater
4.84 out of 5 average rating, 76 reviews
Luxe indoor pool tree house minutes to Chicago
5.0 out of 5 average rating, 3 reviews
Spacious 2BR in The Loop Downtown Resort Amenities
4.89 out of 5 average rating, 87 reviews
Chic Fulton Market Oasis + Curated Comfort & Style
4.71 out of 5 average rating, 62 reviews
Schaumburg Woodfield Pool House 4bedroom 2.5bath
4.77 out of 5 average rating, 43 reviewsCondo rentals with a pool

Pond View, Washer Dryer, Non Smoking, Pet Free
4.88 out of 5 average rating, 58 reviews
Red Door
5.0 out of 5 average rating, 11 reviews
Best view and luxury style, Located in Downtown

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
4.96 out of 5 average rating, 141 reviews
"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
4.96 out of 5 average rating, 122 reviews
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
4.96 out of 5 average rating, 123 reviews
Smoke & Pet Free, Washer Dryer, Fireplace, Balcony
4.82 out of 5 average rating, 71 reviews
Pond View, Washer Dryer, Non Smoking Community
4.88 out of 5 average rating, 52 reviewsOther vacation rentals with a pool

Forest Park Oasis - Dog Friendly - Parks - the "L"
4.97 out of 5 average rating, 34 reviews
Upscale High-Rise Apt · Rooftop Pool + Views
4.92 out of 5 average rating, 50 reviews
Chicago Burbs Gem | Garage, King Beds, Gym, Pool!
5.0 out of 5 average rating, 6 reviews
360RoofSKYview|ARTy|Garage+HotTub|EVTesla|Sleeps12
4.9 out of 5 average rating, 20 reviews
Loop 1BR | Steps to Millennium Park & Bean
5.0 out of 5 average rating, 16 reviews
Wabash 4BR | Pool, Free In/Out Parking 3
5.0 out of 5 average rating, 3 reviews
3BR Luxury Suite w/Gym and Balcony
4.83 out of 5 average rating, 47 reviews
Play in the Windy City and Rest by ‘The 606’
4.61 out of 5 average rating, 142 reviewsWhen is the best time to visit Evanston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 4,649 ZAR | R 4,226 ZAR | R 3,950 ZAR | R 5,006 ZAR | R 5,949 ZAR | R 7,412 ZAR | R 4,925 ZAR | R 4,535 ZAR | R 3,933 ZAR | R 4,860 ZAR | R 4,340 ZAR | R 4,015 ZAR |
| Avg. temp | -4°C | -2°C | 4°C | 10°C | 16°C | 21°C | 24°C | 23°C | 19°C | 12°C | 5°C | -1°C |
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- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- Indiana Dunes State Park
- 875 North Michigan Avenue
- Six Flags Great America
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Frank Lloyd Wright Home and Studio
- Beachwalk Vacation Rentals
- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Washington Park Zoo





