Holiday rentals with a hot tub in North Side

Jacuzzi|Movie Theater|Games|Arcade|Gym|Kid's Space

Welcome to Portage Park! This beautifully remodeled 5-bedroom, 3-bathroom luxury style home is spacious 2,200 sq ft retreat designed for families, friends, and large groups of up to 16 guests. With 2 levels of living space, hot tub backyard, fun games, gym and a one of a kind entertainment basement inluding a home theater, game station for kids, game table & arcade machine, King Master with a private string light filled outdoor deck, we have everything you need for a memorable Chicago vacation!

*New* Luxury Wrigley Penthouse, Free Parking

✨ NEW Guest Favorite in Chicago Wrigleyville! SPACIOUS 3BR, 2.5BA DUPLEX, UP TO 12 GUESTS w/ NEW FURNITURE, BEDS & GAME ROOM ✨ A standout stay in Chicago — nothing else like it! Just a 5-min walk to Chicago Red Line Station (10 mins to Downtown Chicago!) & only 5 mins to Wrigley Field. Walk to cafes, shops, parks & more. Includes FREE parking, fast Wi-Fi, foosball & arcade games. Perfect for friend groups, families, corporate housing, and digital nomads! A perfect score in the heart of Chicago!

The Spa of Downtown Whiting

so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Andersonville Luxe Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape. The pool and spa are heated heated through 12/31.

Hygge Hideaway

Experience the perfect blend of historic charm and contemporary amenities in this expansive 2-bedroom apartment located in Chicago’s vibrant Lincoln Square neighborhood. Built in 1924, this updated residence offers a unique and artsy ambiance, providing a cozy retreat for families, couples, and friends alike. A grocery store is across the street, and a bakery and coffee shop are steps from the apartment. It’s also about a ten-minute walk to the Brown Line station, restaurants, shops, and more!

Elegant 4bedroom, 5 bathroom home on a great block

Elegantly decorated home great for families or large groups. Enjoy a lush backyard, garden, grill, a pergola, 4 fireplaces, hot tub in primary bedroom and a pool table. The glam dining room is a splendid space to host family/friend dinners. We offer plenty of utensils, pots/pans and glassware. Our kitchen and first floor bathroom, are newly remodeled. Entry into the home is quick & easy with a contactless access code. Parking is ample. Crib, packnplay, and highchair are available upon request

Stunning modern home with a lovely backyard

Beautiful modern home in Evergreen Park, not far from Chicago! Features one bedroom, a sofa bed, and two full bathrooms. Enjoy a fully equipped kitchen perfect for home-cooked meals. Step outside to a private backyard patio with an inflatable hot tub(months of May-September: MUST REQUEST) and cozy fireplace, ideal for relaxing evenings. Experience the perfect blend of peaceful suburban comfort and easy access to all the excitement, dining, and attractions the city of Chicago has to offer!

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

Entire Cozy Townhouse

Take it easy at this unique and tranquil getaway. Comfortable and convenient to everything. The lake is a 5-10 minute walk, and so are the grocery stores. The train is right outside the house, literally across the street. The CTA purple and red line trains run through the city and some suburbs. The train will take you to downtown Evanston in 10 minutes ...or to downtown Chicago in 20 minutes. Ask me about the bikes and cars available for rent. This property is not ADA compliant.

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. The property has a parking slab in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions you may have before booking. NO CHORES! Hot tub 5-6 Person Spa

Belmont Pleasures - hot tub / arcade gaming room

Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.