
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 $20 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”
LocationValueOutdoor spaces

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!
FamilyLocationPool

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 Unit Highlights: - Stunning views of the city - Black-out curtains & roller shades - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modern design
LocationValueDecor

Harmony of Evanston 1 BDR Exec Suite w/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. 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
ValueLocationBathroom

DTown Penthouse 2bd +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, & more! ✅1 Free parking pass ✅FAST WIFI ✅En-suite Laundry ✅KING beds ✅Private Rooftop Deck w/ stunning views ✅Amenity Floor (Gym, Pool, Lounge, Doggy Park) ✅ 1 block from Red "L" subway ✅Close to Grant Park, The Bean, Soldier Field, Museums
LocationValueAmenities

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.
FamilySleep qualityWifi

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.
ValueFamilyComfort

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony
Space to live, space to play, space to call home. Our spectacular Two Bedroom Suites boast 1,080 – 1,170 sq ft of modern living space and feature a fully-equipped kitchen, open concept living and dining area, two spa-inspired bathrooms, bedrooms with king beds and an open-air balcony. All suites also feature in-suite laundry, premium appliances, flat-screen TV, complimentary WiFi and local calling.
ValueLocationCleanliness

Riverwoods Nature Retreat
Make some memories at this unique and family-friendly place. A peaceful zen mid-century modern oasis. Relax in the hot tub. Play in the tree house. Tell stories by around the outdoor fireplace Curl up to a book in the hammock. Snuggle by the indoor fireplace and play Pictionary. Central to downtown Chicago, Lake Michigan, Milwaukee and Kenosha. We are a mid century paradise.
FamilyLocationBackyard

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.
LocationValueLaundry
Popular amenities for Evanston rentals with a pool
House rentals with a pool

PRIME 2BD Designer Retreat & Pool |Parking| Patio
LocationFamilyParking

Rosemont 4BD2BA house with Pool
FamilyValueCheckout

The Gathering House & Cinema
FamilyLocationComfort

Spacious 2BR in The Loop Downtown Resort Amenities
ValueLocationHospitality

Schaumburg Woodfield Pool House 4bedroom 2.5bath
LocationFamilyHospitality
Condo rentals with a pool

Pond View, Washer Dryer, Non Smoking, Pet Free
LocationValueAccuracy

Red Door
LocationHospitalityCleanliness

Pond View, Washer Dryer, Non Smoking Community
LocationFamilyComfort

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony
LocationValueLaundry

Iconic Style, Charming Lake View
Other vacation rentals with a pool

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

Luxury South Loop Apt
LocationAmenitiesCleanliness

Long term rental-1 b pool house-no pool parties!
FamilyLocationGetting around

Spacious 1-Bedroom + Den in the Heart of Chicago
ValueFamilyLong stay

Gold Coast Luxury: 2BR with Sweeping City Vistas
LocationValueKitchen

33rd-Floor Penthouse with Breathtaking Views
FamilyLocationParking
When is the best time to visit Evanston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $286 | $260 | $243 | $308 | $366 | $456 | $303 | $279 | $242 | $299 | $267 | $247 |
| Avg. temp | 25°F | 29°F | 39°F | 50°F | 61°F | 71°F | 75°F | 74°F | 66°F | 54°F | 41°F | 31°F |
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- Wrigley Field
- Soldier Field
- United Center
- Lincoln Park
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- University of Chicago
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Donald E Stephens Convention Center
- Union Park
- Beachwalk Vacation Rentals
- Washington Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
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