Vacation rentals with a hot tub in South Side

Find and book unique hot tub rentals on Airbnb

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Popular amenities for South Side hot tub rentals

House rentals with a hot tub

Guest favorite
A spacious living area features a blend of warm wall colors and modern decor. Comfortable seating includes a light-colored sofa and a wooden chair. A fireplace is highlighted on one wall, accompanied by a ceiling fan and natural light from large windows.
Home in Chicago
4.85 out of 5 average rating, 318 reviews

Lux Urban 3BR/3BA Duplex + Parking!

MariaRating, 5 stars1 week ago
This was our third time staying at this property and we’re looking forward to stay again next time we’re in Chicago. Hans was very responsive and easy to communicate with. The place is spacious and comfortable. It’s quite, full equipped kitchen and nice backyard. I highly recommend this place
Guest favorite
A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.
Home in Bloomingdale
4.92 out of 5 average rating, 52 reviews

Now Open: Heated Pool with Entire House

AmyRating, 5 stars1 day ago
Really great place to stay, super responsive host! The pool was pretty great and so was the hot tub! Great location too, lots of stores, restaurants around, and parks like the Busse Woods (it’s huge and lots of walking paths)!
Guest favorite
The image displays a well-maintained exterior of a house featuring a small private yard. Lush green grass surrounds the structure, along with blooming hydrangea plants. A half-covered door is visible on the side, with a vine growing along the wall, contributing to the natural charm.
Home in Chicago
4.86 out of 5 average rating, 77 reviews

Entire house in Lakeview with yard and garage

AnhthuRating, 5 stars1 month ago
Loved our stay at Arturo’s place. The location was super convenient and only a 10 minutes walk to the red line. We were able to grab coffee and food within a 5 minutes walk. We will definitely stay again if we’re in town.
Superhost
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 Chicago
4.88 out of 5 average rating, 56 reviews

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars1 week 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!
Superhost
An open living space is highlighted by a stone fireplace and a large television mounted above it. A comfortable sectional sofa surrounds a round coffee table, while natural light fills the room through large windows. A dining area can be seen in the background.
Home in Homewood
5 out of 5 average rating, 8 reviews

Fore! Peace & Love @ Golf House

SolodineRating, 5 stars3 weeks ago
Beautifully decorated home, lots of amenities and natural light. Home looked better than the pictures. Would definitely book this home again.
Guest favorite
The kitchen features a spacious island with four bar stools, surrounded by dark cabinetry. Exposed wooden beams and warm hardwood flooring complement large windows, offering natural light. Countertops are finished in sleek granite, creating an inviting space for culinary activities.
Home in Chicago
4.95 out of 5 average rating, 38 reviews

Mid-Century Gem By United Center: Hot Tub & Sauna

BlaireRating, 5 stars6 days ago
We loved our stay here. A few bus stops away from lots of shops and restaurants. Great kitchen and amenities. Perfect couch for movie night.
Superhost
A three-level mansion is shown from the front, featuring warm-toned wooden railings and steps. The entrance is framed by a decorative light fixture above the door. Lush greenery surrounds the property, complemented by a clear blue sky and golden foliage framing the scene.
Home in Chicago
4.69 out of 5 average rating, 128 reviews

6-Bed Family Mini-Mansion for 12 Parking & Hot Tub

AnastasiaRating, 5 stars1 month ago
I truly fell in love with this home. Spot on with the photos and descriptions. Very easy to communicate with Pam, and she offered as much assistance a needed, if needed. If you have a larger group needing accommodations this is a great space. The location was very close to the expressway and is 30 minutes from Navy Pier and downtown Chicago.
Guest favorite
A spacious living area features a large sectional sofa accented with colorful cushions. A stylish coffee table sits on a decorative area rug. Bright overhead lighting illuminates the room, enhancing the open layout that connects to dining and kitchen spaces.
Home in Chicago
4.93 out of 5 average rating, 72 reviews

7 Bed Oasis with 5 Baths, Hot Tub, Sauna, Game Rm

TiokoRating, 5 stars2 months ago
Patty was extremely responsive prior to our visit to Chicago, during and post our stay. She also immediately addressed and resolved our cosmetic and minor concerns. Patty was beyond accommodating, kind, accessible, and understanding of our needs and expectations as we were traveling from three different states and with family members ranging for the age of 3 to 85. We booked this Airbnb for our family of 16 for Easter weekend and EVERYONE loved it. It was important that our elders were comfortable, safe and enjoyed themselves, they were sooo impressed and happy. The space is huge and perfect for entertainment. There are a ton of activities available and enough room for everyone/couples to have their own bed/room. With 1.5 kitchens including two stoves, it was convenient, as we cooked breakfast, lunch, and dinner each day in large quantities. The home was beautiful, comfy and we felt right at home! We highly recommend and can’t wait to book this Airbnb for our next trip to Chicago!

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