Pet-friendly holiday rentals in Skokie

4.99 out of 5 average rating, 149 reviews

A modern kitchen showcases sleek white cabinetry and a large island with seating for three on black stools. Open shelving displays various glassware. A stainless steel range hood is positioned above the gas cooktop, while natural light fills the space through windows.

Flat in Edgewater

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

4.96 out of 5 average rating, 188 reviews

A private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.

Home in North Park

Chicago River House -BBQ Oasis now open!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

4.92 out of 5 average rating, 121 reviews

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.

Flat in Evanston

New 3bd/1.5 bth Apt w/private prkg

A perfect hideaway! This quiet, secluded unit is nestled in lush greenery within walkng dist (1.5M) to NWU. Enjoy our renowned restaurants and theaters, plus easy access to downtown Chgo’s many attractions via the Metra; Sleeps up to 7 guests, with 2 queen beds, 2 single beds, and an 8-foot couch in Liv rm; Ultra-modern kitchen equipped with everything; Dedicated parking space in rear of the bldng; free high-speed Wi-Fi is included. Host lives nearby and responds promptly to any inquiries

4.78 out of 5 average rating, 539 reviews

A modern kitchen area features a wooden accent bar with four metal stools. Stainless steel appliances, including a refrigerator and stove, are visible. A wall clock adds a functional element to the open concept design, with neutral tones enhancing the spacious ambiance.

Flat in Park Ridge

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level garden apartment one bedroom one bath. Older building with wooden floors. If hearing people upstairs walking can bother you , do NOT book it please .Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10min to outlets Absolutely NO parties, NO gathering Quiet hours 10 pm till 6.00 am

4.88 out of 5 average rating, 181 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.

4.97 out of 5 average rating, 102 reviews

The spacious family room features a high vaulted ceiling with exposed wooden beams. A stone fireplace provides a central focal point, and a large TV is mounted above it. Comfortable seating is arranged for relaxation, complemented by a stylish area rug.

Home in Des Plaines

NEW~2 Spa Baths~Game Room~Prime Area~Big Yard~

✅Updated Home- RARE 1/3+ Acre Fenced Yard 🏠 ✅Huge Vaulted Ceiling Family Room 🛋️ ✅2 Full Updated Bathrooms on Main Level🪥🛀 ✅Game Room w/Air Hockey & Basketball🏒🏀 ✅Dining Room Seats 10🪑 🍽️ ✅Quiet Neighborhood + Convenient Location🏘️ ✅Open Kitchen Floorplan 🍳👨‍🍳 ✅Outdoor Seating🌳 ✅EZ Driveway Parking for 4 Cars🚗🏎️ ✅Close to O’Hare Airport(8 Min)🛫 ✅Close to Stephens Convention Center(12 Min)👨‍👩‍👧‍👧 ✅Close to Allstate Arena(7 Min)🎤 ✅Close to River’s Casino(8 Min)♥️🎰

4.98 out of 5 average rating, 106 reviews

The exterior of a three-unit building features a blend of brick and stone elements, with large windows providing ample natural light. A well-maintained lawn includes shrubs and small trees, complemented by a walkway leading to a blue door beneath a covered entryway.

Flat in Evanston

3 BR Evanston Apt near Chicago

3 Miles to Northwestern and 2.5 to Loyola Universities. Enjoy local shopping, entertainment & restaurants in Evanston. Walk, bike or drive to Lake Michigan's beautiful beaches. CTA to Chicago nearby. Two BRs with king beds and a third BR with a full. LR has turntable, records, Netflix, Max, Disney+, Hulu... Enjoy a ping pong table and puzzles. Work space in two bedrooms. Kitchen has a stove, oven, microwave, coffee maker, and toaster. Free off-street parking.

4.97 out of 5 average rating, 204 reviews

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.

Flat in Evanston

Stunning, Sunny Flat with Beautiful Backyard

Home away from home in a wonderful and walkable Evanston neighborhood, convenient to downtown, Lake Michigan, Northwestern and more. Treat yourself and your family to this wonderful two-bedroom, masterfully remodeled flat, with all the conveniences and comfort. Off street private parking. Recent updates: New king size bed, 65-inch HD TV, washer & dryer, and more. We follow EPA/CDC protocol and prepare for your stay with intensive cleaning and disinfecting.

4.98 out of 5 average rating, 116 reviews

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.

Home in Chicago

Victorian House in Heart of Rogers Park

Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

4.92 out of 5 average rating, 104 reviews

A well-maintained brick home features a landscaped front yard with lush green grass and a pathway leading to the entrance. Two decorative wall planters are visible beside the windows, and a wooden bench and small table are placed on the front porch.

Home in Evanston

NorthShore Nest by NU & downtown Chicago

Close to downtown Chicago & downtown Evanston! Wi-Fi, family friendly. Near restaurants, movie theater, shopping, Northwestern University and the lakeshore. 2-car garage. Smart tvs in two bedrooms and 65” tv in living room, all have Amazon Prime. Highchair, baby monitor, pack 'n' play, children's books and toys. Office space, wi-fi; fenced in backyard with patio furniture and string lights, outdoor fireplace.

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, 139 reviews

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!

4.77 out of 5 average rating, 662 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.

Apartment 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.

Popular amenities for Skokie pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.98 out of 5 average rating, 113 reviews

A spacious kitchen features sleek black countertops and a large central island. Stainless steel appliances include a refrigerator and a gas range. Natural light enters through the windows, illuminating decorative plants and kitchen essentials arranged on shelves.

Home in North Side

Flat in Lincoln Park 2-Flat Central to Everything

4.93 out of 5 average rating, 165 reviews

A spacious living area features a vibrant orange sofa adorned with green and beige throw blankets. A stylish coffee table holds decorative items, while a large houseplant adds a touch of greenery. Natural light fills the room, highlighting the wooden staircase in the background.

Home in Avondale

BoHo House - A Chic, 1903 Chicago Workers Cottage

4.91 out of 5 average rating, 167 reviews

A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.

Home in Chicago Ridge

Quiet cul-de-sac with huge fenced in backyard

4.86 out of 5 average rating, 143 reviews

The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.

Home in Naperville

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

4.97 out of 5 average rating, 127 reviews

The modern kitchen showcases sleek white cabinetry and a spacious island topped with a white marble surface. Stainless steel appliances, including a gas stove and a refrigerator, are complemented by glass-front cabinets displaying elegant dishware. Soft blue lighting highlights the room's contemporary design.

Home in Portage Park

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

4.97 out of 5 average rating, 153 reviews

The living area showcases a dark blue accent wall, complemented by a modern light fixture. A cozy sectional sofa is framed by two framed artworks, while a round coffee table holds decorative items. An adjacent dining space features a light wood table surrounded by chairs and a built-in cabinet.

Home in Lincoln Park

Charming 3-BED in Lincoln Park/ Old Town & Parking

4.98 out of 5 average rating, 132 reviews

A sunlit living area features large windows allowing natural light to fill the space. Comfortable seating options include a light-colored sofa, two patterned armchairs, and a wooden dining table for four. A side table with a lamp adds a subtle touch of warmth.

Home in Forest Park

Gather in Spacious 3 Bedroom 2 Bath Retreat

4.99 out of 5 average rating, 135 reviews

The spacious living area features large windows that provide ample natural light. A comfortable gray sofa with patterned cushions is positioned beside a coffee table, while a small armchair and plants enhance the inviting ambiance. Decorative elements include a rug and a stylish plant stand.

Home in Lake View

Huge Sunlit Gem, Free Parking, No Cleaning Fee

Pet-friendly home rentals with a pool

4.91 out of 5 average rating, 148 reviews

Home in Highland Park

2-Acre Highland Park Retreat with Heated Pool ~ 5*

4.84 out of 5 average rating, 104 reviews

A modern living area features a light-colored sofa adorned with decorative pillows, set against large floor-to-ceiling windows that offer views of the city skyline. A textured area rug defines the space, while a coffee table displays artfully arranged decorative items. A dining table with black chairs completes the setting.

Flat in West Loop

Top Floor Views + Central Comfort

4.89 out of 5 average rating, 66 reviews

A spacious living area features a large sectional sofa set around a modern coffee table with a textured surface. Natural light floods in through large windows, illuminating a neutral color palette. Decorative plants and stylish furniture pieces enhance the contemporary design.

Flat in Printer's Row

Downtown Penthouse Lake Views #1|Gym, Parking+Pool

5 out of 5 average rating, 16 reviews

A comfortable living area is presented with two soft armchairs and a light-colored couch. A media console houses a Roku TV, while a decorative electric fireplace offers warmth. Artwork adorns the walls, and natural light enters through a window with blue curtains.

Townhouse in Forest Park

Forest Park Oasis - Dog Friendly - Parks - the "L"

4.52 out of 5 average rating, 21 reviews

A spacious bedroom with large windows provides an expansive view of the city skyline. The comfortable bed is flanked by bedside tables with lamps, and art pieces are displayed on the wall. Natural light brightens the room, enhancing its modern aesthetic.

Flat in Fulton Market

Level One Bedroom Suite | Fulton Market

4.81 out of 5 average rating, 48 reviews

The exterior of a charming cottage is showcased, featuring a sleek dark grey facade. A series of stairs lead up to the entrance, flanked by a decorative black railing. Lush greenery surrounds the base, enhancing the inviting appeal of the home.

Flat in Bridgeport

Modern unit in Bridgeport-Chicago

5 out of 5 average rating, 9 reviews

A spacious living area features a light-coloured sofa set positioned around a wooden coffee table, with a television mounted on the wall. A large area rug enhances the space, while plants and natural light provide a fresh atmosphere. Dining space is visible in the background.

Home in Schaumburg

Paradise with Pool & Games

4.86 out of 5 average rating, 59 reviews

An open living area features a large, light-colored sofa that invites relaxation, paired with accent chairs in green. Sunlight filters through expansive windows, offering views of the city and lake. Artwork adorns the walls, with a dining table positioned in the background for gatherings.

Flat in Magnificent Mile

Luxury Designer Penthouse West |Pool| Gold Coast

Private, pet-friendly home rentals

4.96 out of 5 average rating, 133 reviews

The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.

Apartment in Avondale

Lovely top floor 2BR/2BA, steps from everything!

4.95 out of 5 average rating, 305 reviews

A warm living area features a black leather sofa adorned with colorful throw pillows. A glass coffee table rests on a patterned rug, while two accent chairs provide additional seating. Natural light streams in through a window, complemented by decorative plants and wall art.

Flat in Logan Square

Cozy and Spacious! Logan Square Apartment

4.93 out of 5 average rating, 89 reviews

A shaded outdoor deck features comfortable seating arrangements with deep blue cushions. A wooden coffee table occupies the center, while a grill is positioned at one side. Soft lighting enhances the cozy atmosphere as the sun sets in the background.

Home in Skokie

Luxe Limewash Getaway w/Sun Deck

4.99 out of 5 average rating, 210 reviews

A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.

Apartment in Lake View

RockStar Pad W3A BoysTown/Wrigley Field/Parking

4.96 out of 5 average rating, 147 reviews

The modern kitchen features navy blue cabinetry and a central island with seating for three. Stainless steel appliances include a refrigerator, stove, and dishwasher. Pendant lighting hangs above the island, and a window provides natural light, complementing decorative wall art.

Flat in Wicker Park

Stylish 2BR stunner w/ unbeatable location

Apartment in Lincoln Square

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.

4.98 out of 5 average rating, 443 reviews

Lincoln Square Gem!

4.87 out of 5 average rating, 38 reviews

An inviting collage displays the exterior view of a charming house with a well-maintained lawn surrounded by lush greenery. Adjacent images highlight a game room featuring a pool table and a cozy movie room. A comfortable seating area is visible, alongside an outdoor patio space.

Home in Skokie

Urban Oasis | Kid Friendly | Quiet Street