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”

4.98 out of 5 average rating, 211 reviews

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

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

4.96 out of 5 average rating, 141 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

Enjoy your stay at our family's Serene Lake condo with outdoor pool. NEWLY UPDATED Stylish and comfortable with amenities for any family to feel at home. Part of Interlaken community and set on Lake Como, we are surrounded by peaceful woods and often seen wild life, yet a quick drive into down town Lake Geneva, William's Bay and Fontana. Enjoy golfing, dining, water sports and all the region has to offer, then cozy up and relax with a view. NO RV, BOAT or TRAILER parking is allowed.

4.98 out of 5 average rating, 150 reviews

Cozy Lake Geneva Retreat | Amenities | WiFi

Discover Blue Lakes Escape, a newly-redecorated condo, steps away from Lake Como. Relax in the spacious great room with a smart TV, fireplace, desk area & access to quaint patio. Sit outside with a coffee, a good book, or a delicious BBQ. Enjoy free access to the shared amenities, including an outdoor pool, sports courts, & walking trails. Lake Como – 6 min walk Lodge Geneva National – 6 min walk Downtown – 8 min drive Book For Lasting Memories In Lake Geneva—See Details 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.

4.97 out of 5 average rating, 155 reviews

Magnificent waterfront views & cozy fireplace

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

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!

4.96 out of 5 average rating, 188 reviews

Relaxing Villa with Amazing Amenities!

Resort day passes included with booking! Hot tub, indoor and outdoor pool, outdoor bar and fire pit, sauna, the list goes on! Only five minutes from downtown Lake Geneva, this second floor condo offers the best of both worlds. Enjoy the laid back Lake Como attractions, or have a blast in Lake Geneva! This hidden gem is perfect from golfers (only 5 minutes from Geneva National) to families. Give us a try, and enjoy a discount on your second stay!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Elgin rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Fontana-on-Geneva Lake

5 out of 5 average rating, 16 reviews

Abbey Springs Home! Hot Tub + Golf Cart

KathyRating, 5 stars1 month ago

A wonderful home that was well appointed, clean & a great location! We hosted Easter here with my adult Kids and grandson. We all enjoyed the beautiful surroundings and all the wildlife-many deer and even a coyote! So much room and a great layout for us to enjoy the home together!

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 stars4 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 stars6 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!!

4.86 out of 5 average rating, 7 reviews

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

4.95 out of 5 average rating, 22 reviews

Home in Schaumburg

Paradise 4BR w/ Pool & Games

MariaRating, 5 stars1 month ago

We recently moved backed to the Chicagoland area from Texas. We needed a place to stay while our Chicago home was being renovated. Lily’s place was perfect. It had everything we needed for the duration of our extended stay. It was well appointed. Exceptionally clean. It had all the amenities necessary for our family to live comfortably and it was close to grocery stores, shopping, restaurants, and downtown Chicago. Highly recommend.

Show all

Condo rentals with a pool

5 out of 5 average rating, 4 reviews

Cozy Condo at Interlaken! Stay & Play on Lake Como

HeidiRating, 5 stars3 days ago

Such a great place! It was in a perfect location, quiet but close to Lake Geneva, Williams Bay and Delavan. The photos and description were accurate. We had everything we needed and the host was responsive. We will definitely be back when we are in the area and in need of an Airbnb.

5 out of 5 average rating, 8 reviews

Glass Vista: Modern 2BR Condo, Stunning Views

JasonRating, 5 stars3 months ago

This place was exactly what I was looking for a weekend with my girlfriend. It was super clean, premium environment, amazing view, and had all the things we would need for a weekend away from home!

5 out of 5 average rating, 20 reviews

Chic Condo in Lake Geneva

KyleRating, 5 stars1 day ago

perfect is the word! we very much enjoyed Chad and Morgan's place. everything as described or better. good location and all the amenities we needed. comfortable bed, nice towels, nice view, overall we were super pleased. definitely worth the stay.

Condo in Fontana-on-Geneva Lake

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).

4.87 out of 5 average rating, 101 reviews

Lake Geneva relaxation!

MikayelaRating, 5 stars4 days ago

Beautiful place with the perfect amenities! Great instructions provided by the host. Friendly neighborhood, and very close to both Lake Como and Lake Geneva. Very glad I chose this Air BnB instead of a hotel!

4.81 out of 5 average rating, 21 reviews

Lake Geneva Gem: Luxury, Comfort & Prime Location

DarrenRating, 5 stars1 month ago

Great location perfectly located between Delavan and Lake Geneva. Views from balcony are amazing for sunset's. So close to Mars resort, Niche wine bar. Great location for week or weekend stay. only downside, which we know before booking is we rented for a month and no laundry facilities on site, so you have to drag laundry to laundromat on weekly basis for long term rental. overall 5 stars across board on this rental.

4.93 out of 5 average rating, 15 reviews

Condo in Geneva

Cozy 2 Bedroom Condo - Lake Geneva

AnnaRating, 5 stars8 months ago

Nice comfortable space, and a good easy location. Walking distance from the lake. Space was even larger than it looked in the pictures, and clean and comfortable.