Family-friendly vacation rentals in Edgewater

A gated entryway is visible, featuring a wooden fence painted in a neutral tone. The gate is partially open, leading into a green space lined with trees and plants. The house entrance is seen in the background, with a clear sky above.

4.93 out of 5 average rating, 459 reviews

Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

Apartment in Andersonville

A red brick three-flat building is presented with large windows and intricate architectural details. Colorful pumpkins are arranged in the front garden, which features lush greenery and blooming flowers. A rainbow flag is displayed prominently by the entrance, adding a touch of vibrant color.

5 out of 5 average rating, 123 reviews

Andersonville 2 bed with modern kitchen + bath

Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

A charming coach house is enveloped in lush greenery, with ivy climbing its brick exterior. Tall birch trees stand on either side, framing a large window that allows natural light to illuminate the interior. The surrounding area features a tranquil courtyard with paving stones.

4.95 out of 5 average rating, 149 reviews

Edgewater, private, charming coach house 1 (of 2) Licensed by the City of Chicago 2209375

Our Edgewater coach house is a haven in the city. A ten minute walk to Hollywood Beach, a fifteen minute walk to fun Andersonville and a five minute walk to the 'L' train for direct downtown access, it is near to everything but feels far away from the busy city. Great restaurants are right around the corner, and Wholefoods is three blocks away. Managed 100% for guests, two independent units are superbly comfortable/ pristine. All essentials and more provided. Enjoy the city and relax at once.

4.97 out of 5 average rating, 134 reviews

A spacious living area features a stone fireplace adorned with a mounted moose head. Natural light filters through the stained glass windows, illuminating potted plants. Black chairs and a neutral sofa are positioned around a wooden coffee table, creating a cozy gathering space.

Guesthouse in Chicago

A bit of the North Woods on Chicago's North Side!

Looking to get away from it all but not TOO far away? Ours is a quiet, screen-free property perfect for a writer’s or artist’s retreat. NU/Loyola parents or alums, stay here when you visit your kids/alma mater. Fantastic renovated livery barn with lots of light, privacy and amenities. Located in Rogers Park, a short walk to Metra and the Red line. Ample street parking nearby. Created for comfort with a splash of Swedish design, enjoy the deck overlooking a tree-filled garden and waterfall.

Apartment in Andersonville

A spacious living room is featured, with a large blue sofa adorned with pink cushions. Two cozy armchairs with blue upholstery flank a glass coffee table, which is positioned on a decorative area rug. A television stands against the wall, while soft lighting illuminates the space.

4.99 out of 5 average rating, 272 reviews

Foster Flat - Retreat to your Home Away from Home

The perfect place to stay for your next trip to Chicago. This fully furnished 2 bedroom/1 bath unit features bright living spaces with modern decor. Located just a few blocks from the heart of Andersonville, you'll find coffee shops, restaurants, shopping and nightlife. Lincoln Square and Ravenswood neighborhoods are also nearby for you to explore. Conveniently located to public transportation (buses, Red and Brown Line trains, as well as Metra), you'll have no trouble getting around town.

Apartment in Edgewater Glen

A spacious living area is highlighted by a light-colored sofa adorned with various cushions. A round coffee table sits in front, complemented by a cozy armchair. The open kitchen is visible in the background, featuring modern appliances and a warm wood finish.

4.94 out of 5 average rating, 101 reviews

1-Bedroom Apt by Andersonville & Lakefront

Spacious, sunny 1-bedroom apartment in peaceful, historic Edgewater neighborhood of Chicago. Overlooks park and is short walk from Thorndale Red Line "L" station, the beach, Whole Foods, and shops, restaurants, and bars in Andersonville. Ideal for up to 4 people, has queen-size bed in bedroom and sleeper sofa in living room. Kitchen is fully equipped with gas stove, microwave, fridge, coffee machine, and utensils. Free high-speed WiFi. Smart TV. Clean and comfortable with modern touches.

4.83 out of 5 average rating, 168 reviews

A spacious living area showcases a light-colored sectional sofa paired with two vibrant blue accent chairs. A round glass coffee table sits at the center, complemented by a light rug. The open kitchen features dark cabinetry and modern appliances, enhancing the contemporary design.

Condo in Chicago

Alluring Condo w/ Pri. Prkng Cls to Transit &Beach

Our 3 bedroom and 2 bathroom condo has a perfect open layout for any size group that is traveling together. You'll have a ton of open space to share and feel at home, while also choosing from 3 bedrooms to get some privacy as well. Each bedroom has a queen size bed, while the master bedroom also has its own full size private bathroom. Feel free to stay in and cook with our fully equipped kitchen, enjoy the 65 inch Roku TV, and gather around the very large island.

The spacious garden studio features a cozy living area with a textured sofa adorned with decorative pillows. A stylish coffee table is positioned in front, complementing an adjacent dining area. The kitchenette showcases modern appliances, while warm lighting enhances the welcoming ambiance.

4.94 out of 5 average rating, 105 reviews

Edgewater Studio on Paulina

Our garden unit is nestled in the charming Edgewater neighborhood of Chicago, just a short walking distance from the vibrant Andersonville area where you will find several shopping and dining options. Situated in a convenient location, our unit offers easy access to public transit options including bus routes and Red Line as well as permitted street parking. We look forward to hosting, where comfort, convenience, and the best of Chicago's neighborhoods await you.

Apartment in Andersonville

A spacious living area is adorned with floral wallpaper, featuring a comfortable gray sofa and a wooden coffee table. Two white chairs are positioned around a woven rug. An open kitchen area is visible, equipped with modern appliances and green bar stools at the counter.

4.93 out of 5 average rating, 155 reviews

Andersonville's Secret Garden: 2 beds, 1 bath

This serene retreat is tucked away amongst the tree-lined streets of the Lakewood Balmoral historic district. Guests can venture just two blocks to dive into the hustle and bustle of Andersonville, with its incredible food scene and unique local shopping spots. Those looking to explore all that Chicago has to offer will enjoy easy access to the CTA redline, major bus routes, and Divvy stations (our shared bike provider).

A cozy living room is presented with a soft area rug and a contemporary ceiling fan. Two armchairs in vibrant colors face a stylish sofa adorned with decorative pillows. A coffee table sits in the center, while a large mirror and art piece add visual interest to the space.

4.98 out of 5 average rating, 120 reviews

Stylish 2BR Andersonville — Walk to Lake & Cafés

Steps to Chicago’s lakefront, cozy cafes, and Andersonville’s best shops. This bright 2BR blends vintage charm with fast Wi-Fi, plush bedding, and a fully stocked kitchen—ideal for couples, remote workers, and weekend explorers. Stroll tree-lined streets, explore the nearby lakefront, or curl up indoors as the seasons change. Enjoy Superhost hospitality for an effortless stay. We’d love to host your next Chicago escape.

Apartment in Lincoln Square

A bright living room features hardwood flooring and a large, comfortable gray sectional sofa. Two unique yellow chairs are positioned nearby. A stylish TV unit and shelves display decor items, while light streams in through multiple windows, enhancing the open and inviting layout.

4.98 out of 5 average rating, 184 reviews

Vibrant & Chic Apt On Quiet St in Andersonville

Welcome to this thoughtfully remodeled 1925’s two-flat building located in the Second Coolest Neighborhood in the US. While this stylish space is the perfect relaxing stay, its location makes it easy for you to get around. *Free street parking You are only: 5 min walk to Clark St & Exceptional restaurants & bars 6 min drive to Lakefront & Lakeshore Drive... 17 min drive to Downtown Chicago...

A modern kitchen is showcased with sleek black countertops and white cabinetry. A tall chair is situated at the kitchen island, providing seating for one. Stainless steel appliances, including a gas stove and microwave, are visible, complemented by warm yellow walls that enhance the space's brightness.

4.81 out of 5 average rating, 131 reviews

Andersonville Garden Living

This is an amazing garden level apartment right off Clark st. with all the shops and restaurants right down the block. Grab a coffee at the Coffee Studio or a drink at Little Bad Wolf . This unit has a brand new kitchen and has a Smart TV with Netflix and a huge living room to hang out, and new bathroom with a large shower. It also has a private bedroom and access to laundry.

Popular amenities for Edgewater family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

A well-lit living space features large windows allowing natural light. A green sofa and two white chairs are arranged around a circular coffee table. A round dining table with wooden chairs is positioned nearby, and a soft area rug adds warmth to the hardwood floor.

Condo in Lake View

4.76 out of 5 average rating, 181 reviews

Modern Wrigley Oasis with Parking!

Guesthouse in Lincoln Square

The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.

4.88 out of 5 average rating, 335 reviews

Private Coach house near Lincoln Square!

4.95 out of 5 average rating, 153 reviews

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Bridgeport

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

Guest suite in Riverwoods

A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.

4.95 out of 5 average rating, 433 reviews

Master qtr close to nature & easy urban facilities

4.96 out of 5 average rating, 278 reviews

A modern kitchen features a large stainless steel island with seating for three. Black cabinetry offers ample storage space, complemented by open shelves displaying various kitchen items. Pendant lights hang above, illuminating a stylish workspace adorned with greenery, while industrial elements add character.

Loft in Wicker Park

Tea Studio in Wicker Park Spring Factory

4.96 out of 5 average rating, 162 reviews

An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.

Condo in West Town

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

4.85 out of 5 average rating, 172 reviews

A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.

Home in Whiting

The Spa of Downtown Whiting

4.97 out of 5 average rating, 143 reviews

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Apartment in Dunning

Belmont Pleasures - hot tub / arcade gaming room

Family- and pet-friendly home rentals

Apartment in Lincoln Square

A bright living area is presented with a patterned armchair and a cozy sofa adorned with a colorful throw. A wooden coffee table is positioned in front, while a window with sheer curtains frames the view of the outdoor porch area.

4.95 out of 5 average rating, 406 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Apartment in North Center

A living room features a comfortable grey sofa with accent cushions, accompanied by a small coffee table. Two lamps provide lighting beside the sofa. A green chair adds a pop of color, while abstract wall art hangs above the sofa. Two windows frame the space.

4.75 out of 5 average rating, 162 reviews

1BR Apartment in Chicago

4.91 out of 5 average rating, 396 reviews

A spacious dining area features a large table surrounded by six chairs. Natural light is provided by two windows with sheer curtains. A unique light fixture hangs above, and a vase with flowers is centered on the table, contributing to the room's welcoming ambiance.

Home in Lake View

Private 3rd Floor Apartment

4.95 out of 5 average rating, 113 reviews

A cozy living room features a large smart TV mounted on the wall, and a plush sectional sofa with a soft throw draped over it. Armchairs are positioned nearby, alongside a wooden bookshelf. A vibrant area rug adds warmth to the space, with a window letting in natural light.

Apartment in Chicago

Cozy Rogers Park 2 Bedroom Flat

4.97 out of 5 average rating, 448 reviews

A bright living area is showcased with large windows allowing natural light. Red and orange artwork adorns the walls, while a gray ottoman centers the room. Seating consists of a gray sofa and an armchair with a geometric pattern, accompanied by decorative lamps on either side.

Condo in Lincoln Square

Lincoln Square Gem!

Apartment in Lincoln Square

A two-flat brick building is set in a green and landscaped area, featuring large windows that allow natural light inside. A set of stairs leads up to the main entrance, which is flanked by plants and outdoor greenery.

4.94 out of 5 average rating, 141 reviews

Beautiful, sunny 2nd floor 3BR/1BA w free parking

Condo in East Rogers Park

A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.

4.93 out of 5 average rating, 269 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Guest suite in Portage Park

A spacious living area features a large television mounted above a low bookshelf filled with books and movies. A wooden coffee table sits at the center, complemented by a light-colored couch. Doorways lead to other areas, with a hint of the kitchen visible in the background.

4.96 out of 5 average rating, 140 reviews

Eddy Street Upstairs Apartment

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 105 reviews

The living area features a comfortable sofa adorned with patterned cushions, accompanied by a stylish coffee table. A modern dining setup is visible in the background, along with sleek kitchen cabinetry. Light from overhead fixtures illuminates the open layout with dark hardwood flooring.

Condo in Evanston

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

Superhost

A modern kitchen with dark wood cabinetry and granite countertops is complemented by stainless steel appliances. A large island with seating for six is positioned next to a dining area featuring a round table for four. Views of the lake are visible through the windows.

Apartment in Magnificent Mile

4.85 out of 5 average rating, 26 reviews

Luxury Designer Penthouse NW | Pool | Gold Coast

Apartment in Chicago Loop

A bright living area features large windows that offer city views, enhanced by natural light. Comfortable gray seating is arranged on a patterned rug, complemented by modern decor and greenery. A flat-screen TV is mounted on the wall, alongside a stylish coffee table.

4.83 out of 5 average rating, 287 reviews

Spectacular 2BR Penthouse in the Loop | Roof Deck

4.91 out of 5 average rating, 103 reviews

A rooftop pool area is shown, featuring a clear blue pool surrounded by lounge chairs in red and neutral tones. Sunlight reflects off the water, and tall buildings are visible in the background, contributing to a lively urban atmosphere.

Apartment in South Loop

The Professional's Playground (2BD / 2BA)

4.9 out of 5 average rating, 554 reviews

A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.

Apartment in Uptown

Whole Flat in Private Club. Walk to L, Dining & Shows

4.9 out of 5 average rating, 119 reviews

A spacious bedroom features large floor-to-ceiling windows, allowing natural light to fill the room. A large bed with neutral bedding is complemented by a contemporary desk and chair setup, which is arranged near a wood-framed lamp. A subtle area rug lies beneath the bed.

Apartment in River North

50th Floor Mag Mile Studio

Guesthouse in Andersonville

An inviting outdoor space features a sleek pool with a gentle water feature, surrounded by neat landscaping. The modern two-story structure rises in the background, complemented by a black umbrella positioned near the water's edge, creating a serene atmosphere for relaxation.

4.97 out of 5 average rating, 31 reviews

Andersonville Luxury Pool Escape