
Vacation rentals with a pool in Dundee
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Dundee
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

The Fox River Farmhouse-walk to downtown and pool
Have FUN ON THE FOX RIVER with the whole family at this spacious green 2300 sqft ranch home steps away from the RIVER, parks, pool, kayaks & bikepath close to HITS EQUEST. CENTER & NW Medicine Field. We transformed this family ranch into a luxe yet cozy home with maple floors &organic premium hotel linens. Enjoy the vast walkout basement with desk/monitor, PINGPONG table, washer/dryer,kids area, stone patio,bags & fire pit/grill. WALK to BOTH Downtown GENEVA & ST.CHARLES, train,pool& bike rental

Spacious 4 Bed/3.5 Bath Sleeps 8+
Just 30 minutes from downtown Chicago! You will love this gorgeous 4-bedroom home perfect for a vacation, staycation or business travel! Walking distance to the playground & walking trails, restaurants and even the local gym! Home has free parking, 3.5 baths, fully finished basement equipped with work-out room! May-Sept you can enjoy the deck, gazebo, outdoor gas grill & heated 27’ pool! Home is pet free and smoke free. Wi-Fi to enjoy your programs on the Smart TV ithrough your personal apps

Paradiso Vacation
Welcome to our home, a sanctuary of comfort, and unique design. This house it's a perfect blend of modern amenities and timeless elegance. The living area features a cozy fireplace, ideal for family gatherings. The kitchen is equipped with top-of-the-line appliances. The master suite is a private retreat, with walk-in closets, vanities, and a shower. A unique feature of this home is the outdoor living space, with a pool, jacuzzi and BBQ grill making it perfect for entertaining or relaxing.

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.

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, and WIFI provided. Washer/Dryer available upon request. Pool is for registered guests only. Owners on site to assist if needed.

Family-sized Indoor Heated Pool & Movie Theater!
**HUGE INDOOR HEATED POOL**THEATER**SLEEPS UP TO 18 MAX** Set on a private and quiet property, this home boasts a 24/7/365 huge heated indoor in-ground pool attached to the house that is yours to use exclusively throughout your stay! The house has a private movie theater and fully stocked gourmet kitchen! Our occupancy is 18 max visiting or staying. Bring your well-behaved, house-trained dog to join you for no additional fee! **30 day rental available** You will not be disappointed!

Paradise with Pool & Games
Welcome to our home. Enjoy lazy summer days by our sparkling pool, where you can soak up the sun and cool off with refreshing dips. Our well-appointed kitchen is ideal for preparing delicious meals together, and the cozy living areas provide plenty of space for relaxation and bonding. With nearby attractions and easy access to downtown Chicago, our home offers the perfect balance of suburban serenity and urban excitement. We can't wait to host you for an unforgettable stay!

"A" Frame Brandenburg Lake
Getaway to a cozy 1 bedroom w/loft for 2, up to 6 people. Full kitchen 1.5 bath all season getaway. There is a piano as well. A tranquil home steps from a private lake. Oak and Pine surround you plus a stone fireplace, it feels like the North Woods. The A Frame guest house shares a 5 acre compound ( total 20 Acres) with the owners residence and caretaker cottage. The Volo Bog 800ft away. No hot tub Nov - May. Swimming pool, June-October often cool to use in early June.

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

Hot tub. Heated Pool. In town location.
In ground pool!! (Seasonal) Rent this entire home, experienced hosts, near town, 5 min drive to Crystal Lake main beach OR Three Oaks Beach/Recreation. Clean, Updated Home, with fenced in yard and pet friendly. 4 beds total (3 bedrooms) and 1 full bath. Fully stocked kitchen with all cooking supplies that you need. Hot tub. Basketball hoop in driveway, bags set in yard, great summertime home! Walk to Marianos/CVS/Walgreens, near it all!

Backyard Paradise/ Private Pool + Peaceful Stay
Welcome to your peaceful retreat near Chicago, surrounded by a beautiful garden perfect for relaxing, morning coffee, or unwinding by the private pool. Step inside and enjoy a cozy Friends-inspired living room full of charm and comfort. Entire two-story duplex is yours—private garden, pool, and gazebo. Complete privacy guaranteed, no shared spaces of any kind. A truly unique stay you won’t find anywhere else—book your escape today!

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.
Popular amenities for Dundee rentals with a pool
House rentals with a pool

Kalo House | Mid-Century Modern Retreat

Navy Graduation Retreat- 4BR Home by Great Lakes

Grand 1800s Victorian Gem: Updated/by Downtown

Getaway near Lake Geneva, Orchards & Pumpkin Farms

Riverwoods Nature Retreat

1/2 mile to NU, 5min walk to Lake, Swim Spa Pool

5 bdrm 7 bed 2.5 bth Ranch w Fenced Yard Sleeps 10

#EnglishPrairieBnB | 4 Bedrooms | 2.5 Baths
Condo rentals with a pool

4/2 Modern Luxury Home on Pistakee Lake with Pool

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Red Door

Best view and luxury style, Located in Downtown

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

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

"Heart of Evanston" 2br +1Bath-0.6miles to NU

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Other vacation rentals with a pool

Fabulous Cabin

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

Spacious 2BR Hideaway | Pool, Gym & Pickleball!

The Bunkhouse at Susanna Farms

Forest Park Oasis - Dog Friendly - Parks - the "L"

360RoofSKYview|ARTy|Garage+HotTub|EVTesla|Sleeps12

Cozy studio near Michigan lake

The Fun Compound: Private Pool on 5 Glorious Acres
Destinations to explore
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- Wrigley Field
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- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Alpine Valley Resort
- Lincoln Park Zoo
- Union Park
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
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- Wilmot Mountain Ski Resort
- Garfield Park Conservatory





