Family-friendly holiday rentals in Evanston

The living area features a spacious sectional sofa and a coffee table at its center. A TV is positioned against a light-colored wall, while a dining space can be seen in the background with a small table and chairs. Natural light is welcomed through multiple windows.

4.96 out of 5 average rating, 314 reviews

Stylish & Comfy Gem near Downtown~Balcony~Parking

My 2nd floor, 2 BD/1BA home sits in a quiet cul-de-sac, about 1 mi from downtown Evanston. A 15-min walk to the Dempster Purple line station, which brings you right into Chicago. Northwestern and Loyola are nearby for a visit too! The area has wonderful lakeside parks and beaches, so no matter the time of year, you'll appreciate the natural beauty! Grocery stores, coffee shops, and restaurants are within walking distance as well. -Electric Fireplace -Fully Equipped Kitchen -Queen Sized Bedrooms

KitchenIndoor spacesDecor

A living area features natural light from multiple windows, complemented by a ceiling fan. A comfortable sofa with textured throws faces a modern fireplace. Two brown armchairs are positioned nearby, and a decorative rug lies under a coffee table, which displays a potted plant and a magazine.

4.99 out of 5 average rating, 114 reviews

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

FamilyKitchenView

4.94 out of 5 average rating, 141 reviews

The historic manor house features a rich red brick facade adorned with lush green ivy. The spacious porch extends from the building, complemented by well-maintained gardens that enhance the inviting exterior. Large windows provide ample natural light, creating an open and airy ambiance.

Guesthouse in Evanston

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house.

KitchenFamilySleep quality

5.0 out of 5 average rating, 101 reviews

The exterior view of the property is framed by lush greenery, including small trees and ornamental plants. A stone pathway leads to the entrance, which features a light-colored door. The building's soft hues complement the natural surroundings under a clear blue sky.

Guesthouse in Evanston

Mr. Hughes’ Attic, an 80s-themed coach house

Welcome to Mr. Hughes' Attic, a private coach house that pays homage to John Hughes (who filmed many of his movies nearby!) Located in NW Evanston, your stay includes a queen bed, full kitchen, laundry, full bath, dedicated workspace, private balcony, free parking, streaming TV, and more. We're a short walk to Central St shops, restaurants and the Metra train, a five-minute drive to Northwestern, and less than 30 minutes to Chicago. Not wheelchair or ADA accessible. License# STR004.

KitchenFamilyWalkability

4.98 out of 5 average rating, 295 reviews

The exterior features a charming two-story home with a welcoming front porch. A set of stairs leads to the entrance, surrounded by well-maintained greenery and blooming flowers. Sunlight filters through the trees, creating a warm and inviting atmosphere.

Guest suite in Evanston

A guest suite centrally located, but so quiet

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my private guest suite w/kitchenette, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

KitchenFamilyLaundry

4.85 out of 5 average rating, 248 reviews

A stylish living area features a comfortable blue couch adorned with decorative pillows. A glass coffee table sits atop an area rug, surrounded by an array of colorful artwork on the walls. A cozy sleeping area is visible in the background, draped with vibrant blankets.

Home in Evanston

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

Indoor spacesFamilyWalkability

A modern living area is presented, featuring a comfortable sectional sofa adorned with yellow accent pillows. A large flat-screen Smart TV is mounted on the wall, providing entertainment options. Natural light filters through the window, highlighting the warm wood flooring.

4.92 out of 5 average rating, 179 reviews

NEW Fam-Frndly 3 bd 1 bth w/ EZ Parking near NU

Relax with the whole family or explore the city at this peaceful newly renovated 3bd/1bth apartment with plenty of free parking and in-unit washer/dryer. You’ll be close to everything when you stay at this centrally-located place. Only 2 mins from DT Evanston and 25 mins from DT Chicago! Just mins away from Northwestern and Loyola Universities. Enjoy the 65in and 55in Smart TVs, listen to your favorite tunes w/ the voice enabled Amazon Echo Alexa speaker, or enjoy family games.

KitchenFamilyHospitality

4.96 out of 5 average rating, 121 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

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. Joy 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, outdoor pool, BBQ and picnic area and beautiful landscaping. Guests can enjoy the Clark Street Beach & Lighthouse

KitchenFamilyOutdoor spaces

5.0 out of 5 average rating, 123 reviews

An open floor plan living area features a spacious couch paired with a dark coffee table. A soft area rug complements the hardwood flooring. The dining area is visible, showcasing a table for six. Large windows provide natural light to the inviting space.

Townhouse in Evanston

The NICEST place in Evanston for Families 1500Main

Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

FamilyKitchenCleanliness

A bright living area features a light-colored sofa accompanied by a dark green armchair. A coffee table with decorative items sits in front of the couch. Framed artwork adorns the walls, and large windows allow natural light to fill the space.

4.8 out of 5 average rating, 108 reviews

Spacious and Newly Renovated 1BR Next to the Beach

1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building. Enjoy our cozy 1BR/1BA apartment near Lake Michigan in Evanston. Features a fully equipped kitchen, a comfortable bedroom with a queen bed, and a clean bathroom. Walk to beaches, the lakefront, and vibrant downtown with shops and restaurants. Easy public transit to downtown Chicago. Book now for a memorable stay!

Indoor spacesKitchenAmenities

4.78 out of 5 average rating, 716 reviews

A modern multi-story building is nestled among leafy trees, featuring large windows and a sleek, minimalistic design. A wooden staircase leads to the entrance, while blooming flowers add a touch of color to the landscaped garden in front.

Condo in Evanston

Spacious Evanston Unit - Walk to Northwestern U

Welcome to my contemporary and spacious garden level unit located on a tree filled, serene residential block in Evanston. Walking distance to Northwestern University, retail areas, trains, golf, and the lovely beaches of Lake Michigan! A Walgreens and a local brewery restaurant are just a few steps away. Plentiful free street parking and free EV chargers one block away.

KitchenFamilyBarbecue

4.92 out of 5 average rating, 142 reviews

A cozy living area features a light-colored sofa and a dark armchair, arranged around a wooden coffee table. A textured area rug lies beneath, and soft light is provided by a floor lamp. Large, partially draped windows allow natural light to enter.

Guesthouse in Evanston

Cozy Guesthouse near NU - next to Lee Street Beach

Welcome to our cozy and comfortable guesthouse nestled on a quiet and beautiful neighborhood in Southeast Evanston. We are 2 blocks from Lee street beach and 10 minutes walking distance to the Main Street El train (purple line) and Metra stop. We are a 10 minute walk to downtown Evanston and Northwestern University. We are 10 miles from downtown Chicago.

KitchenFamilyLaundry

Popular amenities for Evanston family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.88 out of 5 average rating, 390 reviews

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.

Guesthouse in Chicago

Private Coach house near Lincoln Square!

FamilyIndoor spacesCleanliness

4.94 out of 5 average rating, 887 reviews

A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.

Treehouse in Schaumburg

Enchanted Garden Treehouse (Amenity*)

KitchenFamilyBathroom

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, 501 reviews

Master qtr close to nature & easy urban facilities

FamilyKitchenHospitality

4.93 out of 5 average rating, 280 reviews

A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.

Condo in Little Italy

Private hot tub - King bed suite - Free parking

FamilyKitchenSleep quality

4.86 out of 5 average rating, 108 reviews

A spacious living room features comfortable seating on soft gray furniture, including a large chaise and armchairs. Natural light brightens the area, while a gas fireplace is set within a stylish stone surround. A large flat-screen TV is mounted above the fireplace.

Home in Lake View

Entire house in Lakeview with yard and garage

KitchenIndoor spacesValue

4.88 out of 5 average rating, 101 reviews

A spacious living room features a rich blue accent wall and mid-century modern furniture. Two armchairs and a plush sofa are arranged around a low coffee table. A television is mounted on the wall, complemented by decorative wall art. Natural light fills the room.

Home in Westchester

Modern 2Bdrm Westchester/Chicago Home.With Hot tub

KitchenFamilyAccess

4.97 out of 5 average rating, 180 reviews

Condo in West Town

Chicago Oasis | Spa Bath, Patio & Fireplace

Indoor spacesFamilyValue

Condo in Ukrainian Village

The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.

4.98 out of 5 average rating, 121 reviews

Ukrainian Village 3BR/3BA • Private Patio, Parking

Indoor spacesKitchenLaundry

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 303 reviews

The historic home exterior is showcased, featuring a vibrant red facade with white accents. A charming porch adorned with lattice and railings provides an inviting entrance. Lush greenery surrounds the property, complemented by a white picket fence and vibrant landscaping.

Apartment in Wilmette

Spacious Garden Apartment with Sauna and Fireplace

Indoor spacesKitchenCheck-in

4.86 out of 5 average rating, 154 reviews

A shared yard features a lush green lawn surrounded by trees and a fence. A small patio area includes a table and chairs, with an umbrella providing shade. A barbecue grill is positioned next to the side of the unit, and a garden area is visible in the background.

Apartment in Wilmette

Downtown Wilmette Micro Studio

FamilyKitchenQuiet

4.85 out of 5 average rating, 203 reviews

A spacious studio unit features a comfortable bed with a light-colored duvet, complemented by a soft gray sofa. A round coffee table sits between them, and a world map adorns the wall. Natural light filters through the windows, illuminating the open layout.

Guest suite in Skokie

Adorable studio style unit - Self check in ⚡️

FamilyIndoor spacesLaundry

A modern kitchen and dining area are presented, featuring a sleek island with bar stools and a dining table with six chairs. Natural light is provided by large windows, and contemporary fixtures enhance the space's functionality and design.

4.92 out of 5 average rating, 199 reviews

New 3bd/1.5 bth Apt w/private prkg

KitchenIndoor spacesPets

The spacious bathroom features a freestanding tub and a glass-enclosed shower. A large mirror with a decorative frame is mounted on one wall. The floor is covered with a patterned rug, complementing the warm wall color and wood flooring.

4.97 out of 5 average rating, 221 reviews

Stunning, Sunny Flat with Beautiful Backyard

KitchenFamilyDecor

4.95 out of 5 average rating, 120 reviews

A single-story brick house is presented with a spacious front yard, featuring trimmed greenery and a walkway of stone steps leading to the front door. A driveway, visible to the right, accommodates a garage door with a dark finish.

Home in Skokie

Cozy 2 bedroom house/w garage in Skokie

KitchenIndoor spacesDecor

Apartment in Rogers Park Township

An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.

4.9 out of 5 average rating, 219 reviews

Executive Apartment on Lake Michigan with parking

Indoor spacesKitchenDecor

Home in Rogers Park Township

A stately Victorian house is surrounded by a landscaped garden featuring lush greenery and colorful plants. The front porch is framed by pillars and features multiple seating areas. A red front door adds a bold contrast to the dark exterior of the home.

4.99 out of 5 average rating, 135 reviews

Victorian House in Heart of Rogers Park

Indoor spacesKitchenBathroom

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 599 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

KitchenFamilyShared spaces

Condo in Elk Grove Village

The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.

4.92 out of 5 average rating, 123 reviews

Just remodeled apartment close to airport and mall

KitchenFamilyCondition

Apartment in Logan Square

An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.

4.98 out of 5 average rating, 168 reviews

Fun & cozy getaway w/POOL/game room/FREE parking

Indoor spacesKitchenDecor

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.

4.81 out of 5 average rating, 351 reviews

Spectacular 2BR Penthouse in the Loop | Roof Deck

FamilyIndoor spacesAir conditioning

Apartment in Downtown Chicago

A large outdoor pool is surrounded by a modern deck featuring lounge chairs. High-rise buildings provide a city backdrop against a clear blue sky.

4.92 out of 5 average rating, 117 reviews

Highrise Hideout (Fitness Center • Sauna)

Indoor spacesFamilyBathroom

Apartment in Downtown Chicago

A modern kitchen area features a large island with seating for four, complemented by sleek cabinetry. Floor-to-ceiling windows provide expansive views of the city skyline, allowing natural light to fill the space.

4.87 out of 5 average rating, 168 reviews

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

FamilyKitchenBathroom

Apartment in Downtown Chicago

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.

4.9 out of 5 average rating, 138 reviews

50th Floor Mag Mile Views, Balcony, Pool, Gym

KitchenIndoor spacesAmenities