Pet-friendly holiday rentals in Homewood

4.96 out of 5 average rating, 112 reviews

The open living area showcases a cozy seating arrangement with a brown sofa and modern chairs. A ceiling fan hangs above, and the space is illuminated by warm light from the nearby kitchen. A large TV is mounted on the wall opposite the seating area.

Home in Porter

Dunes Homestead - Near Dunes + Lake + Dog Friendly

Welcome to "The Dunes Homestead". Where all pets are welcome! Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally located home. Artfully crafted, this charismatic, dog themed home greets you with all new furniture, a front porch, big yard, and focuses the design around your "man's best friend"! Less than 10 minutes to the Dunes and beaches or head 5 minutes to downtown for food, drinks and plenty of small-town fun. 😁

4.96 out of 5 average rating, 313 reviews

A spacious living area features a comfortable brown sofa, accented by light-colored pillows. A decorative coffee table sits in front, and a dining space is visible in the background, furnished with white chairs surrounding a light wood table. Natural light brightens the room.

Home in Manteno

King-size beds ! All the luxeries of home!

4 minutes from I-57 You will love this 3-bedroom 2 full bathroom home. In the living room there is a 65in Smart TV for your enjoyment. In the Mater & 2nd bedrooms you will enjoy comfy King size beds with king size hotel pillows & 55" smart tv's. In the 3rd bedroom is a comfy queen size bed with comfy pillows & a 55" smart tv. In the 3rd bedroom closet you will find a deluxe queen air bed. We supply bikes for children & adults along with patio table & chairs with outdoor grill with charcoal

4.92 out of 5 average rating, 153 reviews

A single-story ranch-style home is depicted, featuring a brick and siding facade. A two-car garage is positioned on the right side, with a well-maintained lawn and neat landscaping in the front yard. Clear skies and scattered clouds provide an inviting backdrop.

Home in Bolingbrook

Spacious Bolingbrook Retreat w/ Garage & Yard

Relax with the whole family at this peaceful and spacious 3-bedroom ranch home conveniently located near I-55 & I-355. Walking distance to Promenade Mall, restaurants, bars, shopping, Bass Pro Shop. Enjoy self check-in with smart lock, private attached 2-car garage, large backyard, patio, and grill. Perfect for families, work trips, or weekend getaways. Clean, safe, and only 30 minutes from downtown Chicago and major attractions. Self check-in Free parking Fast Wi-Fi Washer/dryer Backyard/patio

4.96 out of 5 average rating, 104 reviews

The modern two-story house is surrounded by landscaped grounds, featuring a mix of wood and dark paneling. A spacious deck extends from the upper level, with seating and hanging planters. A pathway leads to the outdoor dining area, bordered by vibrant flower pots.

Home in Miller

Steps from the beach and a mile from National Park

Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.

4.89 out of 5 average rating, 164 reviews

A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.

Loft in Brookfield

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

4.92 out of 5 average rating, 112 reviews

A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.

Apartment in Homewood

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

4.98 out of 5 average rating, 208 reviews

The exterior of the bungalow features a brick facade with a green accent, framed by well-maintained grass and a neat walkway. Soft evening light casts a warm glow, highlighting the front door and decorative elements near the windows.

Home in Berwyn

RetroModern Bungalow | pet friendly | free parking

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fenced-in, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location—just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage and/or catch the train a few blocks away.

4.74 out of 5 average rating, 149 reviews

Home in Markham

The Country Life! Spacious House.

Live the Country Life in this beautiful suburban home. The entire house is yours to enjoy. Sleeps up to 14* comfortably with 4 bedrooms, 2 bathrooms and kitchen. No smoking indoors but enjoy the outdoors, barbeque in the yard or relax on the deck when weather permits. * No unauthorized events, parties, repast, gatherings or visitors; Your reservation subject to be canceled and/ or $500 FINE. No Refunds! * Extra guest fee over 10 *Small private events may be considered for a fee*

4.94 out of 5 average rating, 178 reviews

Home in Whiting

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

*REQUIRED* ✅ Will you bring a pet? ✅ Have you read and agree to all rules? 🌆 30min drive to downtown Chicago ⭐️ Near Horseshoe Casino, Lake Michigan, Whihala Beach, Whoa Zone ⛳️ Heated basement with mini golf, arcade games and big TV ⭐️ Close To: Wolf Lake, Indiana Dunes, HardRock 🏠 cots, air mattress, futon sofa 🍼 pack & play, high chair avail ❤️ Guests love: -short drive into Chicago -comfortable beds -indoor mini golf -nearby shops & food -heated bidet toilets

4.82 out of 5 average rating, 224 reviews

A cozy living area is displayed with a pair of beige sofas, accented by decorative pillows. Framed wall art complements the decor. A soft rug is positioned on the wooden floor, while a lampshade on a side table adds subtle illumination.

Home in Blue Island

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

4.95 out of 5 average rating, 133 reviews

A charming single-story home is surrounded by lush greenery and colorful landscaping. The house features a light exterior with dark shutters and a welcoming front porch. A small tree adds a splash of color to the neatly manicured lawn.

Home in Munster

Cozy three bedroom home in Munster , Indiana.

Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

4.96 out of 5 average rating, 120 reviews

A spacious living area features a light-colored sectional sofa adorned with soft pillows, positioned beside a wooden coffee table. A decorative area rug adds warmth to the hardwood floor. Natural light enters through a window, complemented by dark curtains. A potted plant and lamps provide additional light.

Home in Munster

Your Quiet Oasis: Cozy & Private

Escape to this private 2-BR home, perfect for remote workers, cyclists & brewery fans! Enjoy a dedicated workspace with fast Wi-Fi (413 Mbps), a full kitchen, and a spacious, private backyard with a gas grill. This pet-friendly, single-level retreat is your convenient base for exploring nearby nature trails, 6 local breweries, and casinos. Comfortably fits small groups or families seeking a quiet getaway just 30 mins from Chicago.

Popular amenities for Homewood pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.9 out of 5 average rating, 231 reviews

A cozy living room features a leather sofa with decorative pillows, accompanied by two woven chairs. A coffee table sits on a patterned rug, while a potted plant and framed artwork add visual interest. Natural light enters through large windows, creating a bright atmosphere.

Home in Plainfield

Modern Peaceful Home | Firepit | Steps to Downtown

4.99 out of 5 average rating, 81 reviews

A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.

Home in Brookfield

Cozy Home in Brookfield

5 out of 5 average rating, 42 reviews

A spacious wooden deck descends to a fenced backyard featuring a well-maintained lawn. The outdoor seating area includes a large table set for meals, with views of the lake and surrounding greenery visible beyond the yard.

Home in Cedar Lake

Lakeside Loft

Home in Country Club Hills

4.91 out of 5 average rating, 23 reviews

Cul De Sac Jacuzzi home | Near Chicago

4.96 out of 5 average rating, 27 reviews

Home in Valparaiso

Secluded Lakefront A-frame House.

4.89 out of 5 average rating, 107 reviews

A single-story home features a welcoming front porch with seating, surrounded by a well-maintained lawn. The exterior displays a mix of brick and light-colored siding, complemented by neatly arranged shrubs and seasonal decorations. A spacious driveway leads to a single-car garage.

Home in Bradley

Cheerful 3 Bedroom, 2.5 bath central Bradley Home

4.83 out of 5 average rating, 107 reviews

Home in Wicker Park

Private Roofdeck! Location! Parking! Amazing home!

4.94 out of 5 average rating, 109 reviews

A spacious living area features a large L-shaped sofa adorned with decorative cushions. A coffee table sits at the center, complemented by a cozy area rug. A brick fireplace, currently not in use, adds character, while a wall-mounted Smart TV is positioned above the mantel.

Home in Schaumburg

Pet-Friendly Sunny 3BR Near Woodfield & Downtown

Pet-friendly home rentals with a pool

5 out of 5 average rating, 17 reviews

Home in Bartlett

Elegant Executive Residence with Hottub

4.83 out of 5 average rating, 48 reviews

Townhouse in Chesterton

South Shore Escape

5 out of 5 average rating, 19 reviews

A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.

Home in Munster

Munster hide away

4.82 out of 5 average rating, 51 reviews

A modern living area is displayed, featuring large windows that provide city views. A gray sectional sofa complements a circular coffee table on a light area rug. A wall-mounted flat-screen television is present, alongside a cleanly designed console. A spacious bed is visible in the background.

Apartment in West Loop

Level Junior Two Bedroom Suite | Fulton Market

4.77 out of 5 average rating, 53 reviews

A sparkling pool is framed by a spacious patio, featuring lounge chairs and tables for relaxation. Nearby, a playground is visible, along with a covered seating area and a Blackstone grill, all surrounded by greenery and a serene setting.

Home in Plainfield

Pool, 30 mins to CHI, 3 Kings, Outdoor Space, BBQ

4.95 out of 5 average rating, 22 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"

4.59 out of 5 average rating, 32 reviews

A large swimming pool is surrounded by a concrete deck and a wooden fence. Lush greenery is present in the background, adding to the serene atmosphere. A few lounge chairs are placed nearby, creating a space for relaxation.

Home in Miller

Cheerful 4 bedroom 2 king size beds, 2 queen size

4.75 out of 5 average rating, 288 reviews

A bright living area features a comfortable gray sofa and two modern chairs set around a round coffee table. Large windows provide expansive views of the city, while greenery adds a touch of nature to the space. The warm lighting creates a welcoming ambiance.

Apartment in The Loop

Stunning 3BR Penthouse in the Loop | Roof Deck

Private, pet-friendly home rentals

4.83 out of 5 average rating, 36 reviews

A spacious living room features a gray sectional sofa and a round area rug, complementing a stylish coffee table at the center. Natural light filters through sheer curtains, while a piece of abstract wall art adds a pop of color. A potted plant adds a touch of greenery.

Apartment in Thornton

Your quiet south suburban oasis

5 out of 5 average rating, 4 reviews

Apartment in West Town

Bright & Spacious Boho Oasis: A Warm Retreat

5 out of 5 average rating, 23 reviews

Home in Cedar Lake

Cedar Lake A-Frame Near Lighthouse & Public Beach

4.88 out of 5 average rating, 41 reviews

A modern kitchen and dining area feature a sleek island with barstools and a spacious dining table. Pendant lights illuminate the space, while a fruit bowl adds a touch of color to the table. Light cabinetry and an open layout enhance the inviting atmosphere.

Home in Park Forest

Gorgeous home away from home.

4.89 out of 5 average rating, 9 reviews

An open living area features a light-colored sectional sofa with an accompanying ottoman, arranged beside a modern dining space. Natural light filters through large windows, highlighting indoor plants and decorative accents. A granite countertop serves as an inviting transition to the kitchen.

Home in Park Forest

Modern Oasis Getaway Home. Free Cancellation

4.92 out of 5 average rating, 25 reviews

A two-story brick farmhouse is set within a lush green landscape, showcasing a spacious front yard adorned with fallen leaves. Large windows allow natural light to fill the interior, while a covered porch extends from the front entrance, offering a welcoming view of the surroundings.

Home in Valparaiso

Fun at the Farmhouse

4.86 out of 5 average rating, 92 reviews

A two-story house features a combination of brick and siding exterior, bordered by neatly trimmed shrubs. A spacious lawn is visible in the front, with trees providing shade. The driveway leads to a garage around the side, while clear blue skies framing the home complete the scene.

Home in Riverdale

Beautiful , fully renovated