Vacation rentals with a pool in Elgin

4.9 out of 5 average rating, 527 reviews

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”

4.89 out of 5 average rating, 44 reviews

Farm stay in Clare

Haven Estates_: Cozy Barn, Hot Spa & heated Pool

Enjoy a peaceful countryside retreat at this charming Barndominium set on 6.5 private acres, accommodating up to 8 guests This spacious getaway features an 18' x 36' private pool with a hot spa and a solar-heated pool room for year-round relaxation. The Great Room offers open-concept living with comfortable seating, recreation space, and four sleeper sofas. The cozy bedroom includes a king-size bed, while the fully equipped chef’s kitchen boasts an oversized island & a stove with an air fryer.

4.96 out of 5 average rating, 213 reviews

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

4.97 out of 5 average rating, 110 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

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

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

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.

5 out of 5 average rating, 6 reviews

Home in West Chicago

Cloud 9: 4BR, Pool, Fully Fenced

This inviting two-story home is designed for comfort, entertainment, and relaxation. The pool is officially open for the season! Kids love this place—there’s a sandbox, water table, and swings to keep them busy for hours. Enjoy the open-concept layout, a loft for work or reading, and a fun lower-level game room with a pool table. Outside, soak up the sun with outdoor dining, lounge chairs, and plenty of space to unwind. This 4 bedroom home is perfect for your stay!

4.93 out of 5 average rating, 137 reviews

Home in Gary

Bayless Dune Lodge at West Beach - Indiana Dunes!

Bayless Dune Lodge at West Beach is a gorgeous, Lodge-themed home in Miller Beach, Indiana, a scenic community surrounded by the Indiana Dunes National Park! A short walk to one of the finest white sand beaches on Lake Michigan, the Lodge sits on nearly half an acre of land nestled into the "Bayless Dunes Nature Preserve." The property boasts a heated, in-ground swimming pool, pool-side lounge area, two outdoor dining areas, two spa-quality bathrooms and more!

4.97 out of 5 average rating, 109 reviews

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

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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Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 55 reviews

Home in Schererville

Cozy house in Schererville

AnyaRating, 5 stars1 week ago

Very well thought through place for every detail, with a mix of 70s wood style and some higher tech upgrades like the main bathroom mirror with light and anti fog, or sensor lights. Kate was very responsive and accommodating for the 1 baby & 1 toddler we asked for. The place was stocked with all necessary items especially in the kitchen with appliances and cutlery, coffee, tea. There were 2 hairdryers, nice shampoo and conditioner, shower gel.

5 out of 5 average rating, 4 reviews

Home in Des Plaines

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars3 weeks ago

Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

4.92 out of 5 average rating, 51 reviews

Home in Bloomingdale

Now Open: Heated Pool with Entire House

TaraRating, 5 stars1 month ago

Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.

4.89 out of 5 average rating, 63 reviews

Home in Woodstock

Grand 1800s Victorian Gem: Updated/by Downtown

MikeRating, 5 stars3 days ago

Fantastic home, we all loved it and had such a great time! Deirdre was right on top of things, so friendly, it was a delight working with her. The home was beautiful, and looked just like the pictures. What a fantastic experience!

4.92 out of 5 average rating, 26 reviews

Home in Schaumburg

Schaumburg Oasis:Private Pool & Enchanted Garden

SarahRating, 5 stars5 days ago

We stayed here while our floors were being refinished and Marzena’s Oasis did not disappoint! You can tell she takes great pride in her listing; everything was as described and more. The home was very clean with plenty of linens, dishes, and kitchen/pantry supplies. My kids left more crumbs on the floor than usual during breakfast one day…I could not find a broom so I messaged Marzena. She dropped off a stick vacuum AND some delicious treats. Above and beyond to make us feel welcome and comfortable. Thank you for a home away from home!

5 out of 5 average rating, 54 reviews

Home in Genoa City

Relaxing Summer Getaway near Lake Geneva w/ Pool

BenjaminRating, 5 stars2 weeks ago

The house was a perfect fit for my family of 8. The amenities were great and Nicolet provided excellent communication.

4.94 out of 5 average rating, 77 reviews

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!!

Home in Fontana-on-Geneva Lake

4.98 out of 5 average rating, 43 reviews

3 Bedroom A-Frame with Hot Tub & Amenities Galore!

Yifang DaisyRating, 5 stars2 months ago

The spectacular view in a heavy wooded area. Really enjoy it. I would visit again if I am in the area. I especially like the kitchen design.

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Condo rentals with a pool

4.5 out of 5 average rating, 4 reviews

Windmill Cottage at Abbey Springs - Lake Access!

SueRating, 5 stars11 months ago

Our hosts were very responsive to questions. Our first visit to Lake Geneva was so positive. The highlight was gold cart rides to Abbey Sorings resort. The food and service at their grill was exceptional. So much to do right at the resort!!

Condo in River North

4.4 out of 5 average rating, 10 reviews

voco: Balcony & City View

BrookeRating, 5 stars3 weeks ago

Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.

5 out of 5 average rating, 58 reviews

2 BD 2 BA Abbey Villa with Pool

GavinRating, 5 stars9 months ago

Great spot! The condo was clean, comfortable, and quiet. It was a short walk to the beach and restaurants. Mandy’s detailed directions and instructions made checking in a breeze. Our group of four had a fantastic time.

4.78 out of 5 average rating, 181 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

MollyRating, 5 stars2 months ago

Joan's daughter, Rebekah, communicated directly with me through the Airbnb app. She provided detailed check-in instructions, a phone number to contact her, etc. It seems Rebekah lives in Hawaii so please keep note of that for response times, etc. The house was comfortable, very clean, and well-appointed. Joan and Rebekah have a beautiful collection of original art, artifacts, etc. so please keep that in mind if you are bringing small children to the home. Please note that the 1st floor bedroom has a king bed and full bathroom; and the lower level has 2 twin beds in the open area, 1 full bed and 1 twin bed in the first bedroom, and 1 full bed and 1 futon in the second bedroom (including a full laundry and utility room in a closed room).

Condo in Elk Grove Village

4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars2 months ago

I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

Condo in Lombard

4.91 out of 5 average rating, 46 reviews

Pond View, Washer Dryer, Non Smoking Community

AsgharRating, 5 stars6 months ago

Place was neat and very clean, enjoyed our stay, location was great as it was near all the malls and restaurants in Lombard and Oakbrook.

5 out of 5 average rating, 14 reviews

Luxurious Condo Experience at Lakeside Villa |Pool

BrittanyRating, 5 stars1 week ago

Had a wonderful time here for my sister’s bachelorette party. The town home was beautiful and newly renovated. We had an amazing time at the nearby pool and other attractions close by. Overall great stay!