Vacation rentals with a pool in Schaumburg

4.9 out of 5 average rating, 528 reviews

An indoor mosaic-tiled pool is surrounded by a spacious, elegantly arched ceiling. Soft lighting reflects off the water, enhancing the serene atmosphere. Wooden lounge chairs are placed along the poolside, providing a comfortable area to relax.

Apartment in Uptown

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”

4.96 out of 5 average rating, 213 reviews

A serene outdoor area features a curved pool surrounded by a wooden deck and lush greenery. Potted flowers add color to the scene, while a shaded umbrella provides seating comfort. Tall trees offer natural privacy, enhancing the tranquil ambiance of the space.

Guest suite in Bartlett

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

Apartment in Logan Square

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.

4.97 out of 5 average rating, 114 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 suite in Saint Charles

A spacious bedroom features a queen bed dressed in crisp white linens, accompanied by decorative pillows. Soft lighting is provided by a bedside lamp, while an accent rug adds warmth to the wood floor. A built-in shelf displays various decorative items.

5 out of 5 average rating, 292 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

4.97 out of 5 average rating, 116 reviews

Condo in Evanston

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

An inviting backyard scene features a sparkling in-ground pool surrounded by lounge chairs and shaded by greenery. The house's exterior showcases large glass doors that open onto the patio area, providing a seamless connection between indoor and outdoor spaces.

4.87 out of 5 average rating, 30 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

Freshly updated house with in-ground POOL! Minutes to Woodfield mall and restaurants in Schaumburg. One of the only houses with private pool in the area. LOCATION: 35 min to downtown Chicago, 20 min to O'Hare airport, 20 min to Rosemont convention area MASTER BEDROOM extra large for primary guest(s). Unpack and stay awhile with a large walk in closet. Luxurious attached master bathroom with double sink and large walk in shower with bench. Pool is open from May until the end of September.

A bright living area features a light-colored sofa set and a wooden coffee table. A large television displays scenic nature visuals. Soft lighting accentuates neutral-toned walls, while a window with sheer curtains allows natural light to enter the space. Green plants add a touch of nature.

4.95 out of 5 average rating, 22 reviews

Paradise 4BR w/ Pool & Games

Welcome to our family-friendly 4BR 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 ample 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!

4.91 out of 5 average rating, 145 reviews

Home in Highland Park

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

4.84 out of 5 average rating, 389 reviews

A serene outdoor area features a clear swimming pool surrounded by a spacious stone patio. Lush green trees provide natural shade, and several lounge chairs are arranged around the pool, offering ample seating. A gazebo and additional seating are visible in the background.

Chalet in Ingleside

"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 usually June-October often cool to use in early June.

A spacious backyard is illuminated by soft evening light, showcasing a lush green lawn framed by well-maintained gardens. Multiple seating areas are visible, including a hammock, lounge chairs, and patio furniture. A large tree offers shade, while a pool is partially seen beyond the greenery.

4.93 out of 5 average rating, 27 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

Welcome to our uniquely located home!- a serene escape in the heart of Schaumburg. We offer a tranquil garden adorned with fairy lights, custom mushroom decor, and a cozy pergola—perfect for evening relaxation. a short walk to a grocery store, pharmacy, café, and cleaners, everything you need is within reach. Enjoy the spacious, fully fenced backyard with a hidden garden, private swimming pool, propane fire pit, fresh herb gardens, and one-of-a-kind vintage interior design,

4.97 out of 5 average rating, 109 reviews

An above-ground pool is set amidst a lush green lawn, surrounded by trees. The deck area features steps leading up to the pool's edge, where colorful pool floats are visible. The peaceful outdoor space invites relaxation and enjoyment.

Yurt in Homewood

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 4 beds w/sofa sleeper Game Room w/bathroom 1 bed & sofa sleeper Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Breakfast included is 1 dozen fresh eggs!

4.9 out of 5 average rating, 20 reviews

A backyard patio is softly lit by string lights, casting a warm glow across the outdoor space. Paved stones create a welcoming area, surrounded by greenery. Steps lead to a raised wooden deck, enhancing accessibility and inviting outdoor gatherings.

Home in Elgin

Entire Home in Elgin with Pool!

Welcome to our spacious family home in Elgin, featuring a large backyard patio perfect for outdoor relaxation and entertainment. Inside, enjoy a cozy yet modern space with ample room for everyone. The highlight of the home is a fully equipped theatre room in the basement, ideal for movie nights and unwinding after a day of exploring. Perfect for families or groups, our home offers comfort and fun in a quiet neighborhood! Pool open on June 1st

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House rentals with a pool

5 out of 5 average rating, 11 reviews

A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.

Home in Munster

Munster hide away

ChristopherRating, 5 stars5 months ago

Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

A living room is presented with light wooden flooring and a soothing grey wall. Two red sofas are arranged for seating, facing a wall-mounted television. Natural light filters through two textured window shades, and a lamp stands beside the furnishings, adding to the room's cozy layout.

4.79 out of 5 average rating, 14 reviews

Spacious 3 Floor Townhome

RyanRating, 5 stars5 days ago

Place looked exactly as shown on the listing. Alex was very responsive to questions all weekend and was a lot of help.

4.88 out of 5 average rating, 65 reviews

An above ground pool with a diameter of 20 feet and a depth of 4 feet is surrounded by a grassy area and shaded by tall trees. A ladder provides access to the pool, and colorful floats are visible on the water's surface.

Home in Woodstock

Grand 1800s Victorian Gem: Updated/by Downtown

JenniferRating, 5 stars6 days ago

It was wonderful for a family with kids. Very clean. Great location. Comfortable beds. Sound system that you could control from an app and play music in any room. Games in basement were perfect for kids of all ages That was great. Would happily stay again.

4.88 out of 5 average rating, 56 reviews

A cozy loft area features exposed brick walls and wooden beams. A compact sleeping space includes a spacious bed covered in neutral bedding. Two white chairs and a small side table are positioned for seating, with a window allowing natural light to enter.

Home in Lincoln Park

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars6 days ago

Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!

4.94 out of 5 average rating, 77 reviews

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. An island with bar seating is positioned in the foreground, while a spacious archway leads to an elegantly designed hallway featuring artwork and natural light.

Home in Plainfield

Beautiful Spanish style Home (w/inground pool)

BethanyRating, 5 stars1 month ago

Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!

4.9 out of 5 average rating, 63 reviews

A serene outdoor pool is surrounded by a stone patio and well-maintained greenery. Lounge chairs are placed nearby, and vibrant foliage provides a peaceful backdrop. Sunlight reflects off the water's surface, creating a calming atmosphere.

Home in Lake Forest

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars10 months ago

Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!

PatriciaRating, 5 stars5 days ago

The exterior of a mid-century modern ranch home is displayed, featuring a flat roof and a large, contemporary garage door. Lush greenery surrounds the entrance, complemented by a well-maintained lawn. The driveway provides ample space for parking, enhancing accessibility.

Home in Skokie

New place to stay

Luxury fenced in modern ranch

It was a chaotic start to our vacation stemming off my daughter's graduation from Northwestern; however, Jennifer immediately took the stress off my shoulders and welcomed our family to a fabulous stay at her home. Words cannot express how grateful my family is and without Jennifer's help it would not have been as successfull. I highly recommend staying at any of her properties. She will go above and beyond to make sure you're stay is wonderful!

4.86 out of 5 average rating, 7 reviews

A spacious living area is featured, highlighted by a neutral palette and large windows with blinds allowing natural light. A stone fireplace serves as a focal point, complemented by white sofas and an ornate coffee table. A television is mounted above the fireplace for entertainment.

Home in Carol Stream

Spacious 4 Bed/3.5 Bath Sleeps 8+

CarmenRating, 5 stars8 months ago

Beautiful house very clean and comfortable. We'll be back very soon

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Condo rentals with a pool

4.92 out of 5 average rating, 63 reviews

A modern living area features a blue sofa accented by colorful pillows. A flat-screen TV is positioned on a white media console. A round coffee table sits on a textured area rug, with plants adding a touch of greenery. The open kitchen is visible, showcasing light wood cabinetry.

Condo in Downers Grove

Upscale, Washer Dryer, Smoke Free, Pet Free,

ChidoRating, 5 stars3 months ago

I really loved the place—it was cozy, soundproof, and felt just like home. It had a warm, inviting atmosphere and a great sense of comfort. Plus, the neighborhood felt very safe, which made our stay even better.

4.96 out of 5 average rating, 97 reviews

An outdoor pool area is shown, featuring a clear blue pool surrounded by lounge chairs. Trees provide a touch of greenery, while a modern glass structure offers shaded seating. Sunshine reflects off the water, creating a bright and inviting atmosphere.

Condo in Evanston

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

AaronRating, 5 stars1 month ago

I would highly recommend Michelle's listing! The listing is spacious and perfect for a couple or small family (we had our <1 year old). Michelle is communicative, all the instructions are clear, and the location is convenient.

4.73 out of 5 average rating, 55 reviews

A panoramic view of downtown Chicago showcases a skyline filled with modern high-rise buildings. Expansive green spaces and Millennium Park are visible in the foreground, with a large, metallic outdoor concert venue prominently featured. The image captures a clear blue sky and vibrant city life.

Condo in The Loop

2BD Central Downtown Location! Spacious & Cozy

MadleneRating, 5 stars1 month ago

We were very happy with the Apartment, it was clean and perfect size for 4 people. Ana was super helpful and responded immediately, we loved talking to her 😄 For me due to Images, and wrong adress on the public profile, there has been some confusion about the location of the Apartment. All in all: The views are not stunning, but the location is perfect for sightseeing (and price was great location wise)! 😉

4.95 out of 5 average rating, 108 reviews

Condo in Evanston

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

StaciRating, 5 stars2 weeks ago

Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.

A serene bedroom is illuminated by soft purple lighting. A spacious bed with a polka dot blanket is centered in the room. Floor-to-ceiling glass doors reveal a view of a vibrant city skyline at night, with city lights twinkling in the background.

Condo in The Loop

4.45 out of 5 average rating, 11 reviews

voco: Balcony & City View

AmitRating, 5 stars2 weeks ago

gorgeous views and very nice condominium. great balcony and very safe. The elevators were super fast. Even though the actual location is different than the one mentioned in listing, it still wasn't disappointing. There is enough space for a small family or a couple.

A cozy living area is highlighted by a wood-burning fireplace, where a warm fire flickers. A sleek coffee table sits in front of a comfortable sectional sofa, complemented by a textured area rug. Two glasses of wine rest atop the table, adding a touch of relaxation.

Condo in Lombard

4.84 out of 5 average rating, 56 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

LelandRating, 5 stars5 months ago

Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.

An outdoor pool area features a clear, blue body of water surrounded by lounge chairs. Lush greenery is placed in large planters along the perimeter, with a backdrop of modern high-rise buildings and a cloudy sky.

Condo in Magnificent Mile

4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars25 months ago

Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.