Pet-friendly holiday rentals in Waukegan

4.91 out of 5 average rating, 259 reviews

Guest suite in Zion

Cozy Mother inlaw Suite. Private. Next to beach.

30 minutes away from the Navy Base(Graduates). 5 minutes away from the newly renovated Beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags. This Mother in Law suite has tons of natural light. Private access and no shared indoor space. Safe and quiet neighborhood with plenty of wildlife right in the back yard. For nature lover’s this unit is close to the beach and there are walking trails nearby.

WalkabilityOutdoor spacesLayout

4.94 out of 5 average rating, 186 reviews

A cozy living room features a pair of light-colored sofas and an accent chair, positioned around a rustic coffee table. A patterned area rug lies underfoot, while a mirror with a wooden frame and wall art enhance the space. A partial view of the kitchenette is visible in the background.

Home in Highland Park

Cozy 2-Bedroom Cottage Near Downtown Highland Park

Step into a warm, inviting retreat where comfort meets character! This beautifully updated suite features two cozy bedrooms, a private bathroom, and thoughtfully decorated living spaces in a modern farmhouse style. Nestled in the heart of Highland Park, you’re steps from great restaurants, boutique shops, scenic trails, and parks, plus a golf course across the street and just 1.5 miles from Lake Michigan. Whether it’s a family getaway or a business trip, it’s your perfect home away from home!

Outdoor spacesPetsLayout

5.0 out of 5 average rating, 26 reviews

Home in North Chicago

Modern 4 BR 3 miles from Great Lakes Naval Base

Welcome to this modern Getaway next to Base! Make yourself at home in this modern 4BR, 1.5BA -Perfectly located 4 miles from Great Lakes Naval Base. Relax in the bright, open living room with smart TVs, fast Wi-Fi, and plenty of seating for family time. Prepare meals together in a fully stock kitchen, laundry, and private fenced yard with fire pit and BBQ. Designed for Navy Families, and leisure travelers, Enjoy cozy nights by the indoor fireplace and starry evenings around the outdoor fire pit

LocationAccessBeach

4.97 out of 5 average rating, 102 reviews

The backyard features a well-maintained lawn surrounded by gray gravel. A patio area includes a dining table and umbrella. The house is painted in a soft blue, while a grill is positioned near the side of the house. A condo building is visible in the background.

Home in Wauconda

The Adorable "Blue Breeze"!

Enjoy time at our centrally-located, family-friendly home. Close by, you'll find a public fishing dock and the popular Phil's Beach. A peaceful space with an outside patio and grill, perfect for relaxing at end of day. We also have a large driveway that can accommodate your boat making it easy to enjoy a day on Bangs Lake or a short 15 min trip to Fox Lake. Nearby attractions include the Volo Museum, Jurassic Gardens, and Lake County Discovery Museum. Please note the backyard is not fenced in.

PetsOutdoor spacesComfort

4.98 out of 5 average rating, 181 reviews

A private pier extends into the clear waters of Lake Shangri-La, bordered by smooth stones. Benches on the pier provide space for relaxation, surrounded by trees and open skies, creating an inviting view of the serene lake landscape.

Home in Bristol

Lake Home w/View, Private Pier, + Indoor Hot Tub

Wake up to stunning lake views, then spend your days exactly how you want - fishing off your private pier, paddling out in one of the six provided kayaks, or floating in the indoor hot tub while watching the sunrise over the water. Our 3BR/2BA lakefront ranch sits on 200 feet of shoreline with a four-season room that doubles as a game room (pool table included), so there's never a bad weather day. The dock is steps from the back door and ready for swimming, fishing, or bringing your own boat.

Outdoor spacesPetsCondition

A welcoming living area features a plush, light-colored sectional sofa and an elegant coffee table. Soft lighting emanates from a chandelier, enhancing the warm tones of the walls. A decorative console table displays plants and a mirror, while a cozy blanket is draped nearby.

4.94 out of 5 average rating, 110 reviews

*Entire house w/4 LG Bedrms, NAVY 4 miles/baseLake

We are excited to welcome you to this clean and spacious home/perfect location.10 mins /4 miles from Great Lakes. SLEEPS 5- 12!! A"Gathering Place" is for FAMILIES! Stay all together in one place and make memories! Waukegan has parks/cool pl! A Dock/ lakefront, galleries, breweries, restaurants, and more! Near the train station, if you want to travel to Chicago N Suburbs. Close to Six Flags, the Genesee Theatre and the new CASINO! The train is 2 blocks/travels to both Chicago and Wisconsin.

Outdoor spacesWalkabilityIndoor spaces

4.97 out of 5 average rating, 60 reviews

A bright entertainment space features a pool table at its center, surrounded by a cozy seating area with a rust-colored couch and two armchairs. Natural light filters through sheer curtains, highlighting the warm wood flooring and neutral wall tones.

Home in Libertyville

Modern French Escape | Near Base

Welcome to Your Chic French-Inspired Escape! Step into a stylish 4-bed, 2.5-bath retreat blending modern comfort with a touch of France. Just 2 miles from Six Flags, 4 miles from The American Place Casino, and 9 miles from the beach and Naval Station, this home is perfect for families and groups. Enjoy French-inspired décor, office nooks, a pool table, and board games for fun nights. The stocked kitchen makes meals easy. Near highways, shopping, and dining, this elegant getaway has it all!

PetsOutdoor spacesKitchen

4.96 out of 5 average rating, 241 reviews

A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.

Home in Richmond

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

PetsOutdoor spacesCleanliness

4.89 out of 5 average rating, 133 reviews

A spacious living area features a blue couch facing a large television mounted on the wall. A decorative rug complements a wooden dining table set for four, accented with plates and glassware. Natural light filters through large windows, enhancing the inviting layout.

Home in North Chicago

Spacious 2-br, 1 bath home w/AC near Naval Base

Welcome to our cozy and comfortable Airbnb, perfectly located near Naval Station Great Lakes (approximately 5-7 min., 2 miles), Six Flags Great America, and just an hour from downtown Chicago! Whether you're visiting for Navy graduation, family time, business, or a weekend getaway, our home offers the perfect balance of convenience and relaxation. We take pride in providing excellent hospitality and a smooth, stress-free experience from check in to check out.

PetsOutdoor spacesCheck-in

4.89 out of 5 average rating, 102 reviews

A charming brick home is set amidst a lush green lawn, framed by trees and bushes. The two-story structure features a distinctive sloped roof and a welcoming front porch. Natural light enhances the inviting exterior on a clear blue sky day.

Home in Highland Park

A Wonderful Getaway Home on the North Shore!

A perfect place to visit the northern highlights of Chicago! 1/4 mile from Ravinia! 1.5 miles from the Botanic Gardens! 30 minutes from Chicago (an hour and a half from Milwaukee). Close to trains, planes, and easy automobile access. A two-bedroom gem in the heart of so many wonderful things. Other local places include Northwestern University, Lake Forest, Winnetka, and Lake County. I have a cat living here, but he will accompany me when I leave.

WalkabilityPetsAccuracy

4.99 out of 5 average rating, 139 reviews

A cozy sunroom is featured with large windows, allowing natural light to fill the space. A comfortable gray sectional sofa provides seating, accompanied by a decorative pillow. Soft lighting fixtures and a unique chandelier add a welcoming touch to the inviting atmosphere.

Home in Kenosha

6th Ave Harborside

Perfectly located near downtown Kenosha, this cozy and comfortable home makes it easy to enjoy the best of the area. Ride the bikes to the farmers market, stroll to the beach, or spend time along the marina and harbor. The large dining room invites long meals and relaxed evenings together. An ideal home base for a peaceful getaway, visiting family, or attending local events. One night stays are available on a limited basis - reach out for details!

WalkabilityOutdoor spacesIndoor spaces

4.94 out of 5 average rating, 138 reviews

A spacious living area features modern furniture, including a leather sofa and armchairs arranged around a coffee table. A dining table with blue chairs is visible, complemented by large windows allowing natural light. The room has a warm and neutral color palette.

Loft in Libertyville

Historic Downtown Libertyville Loft

Enjoy a stylish experience at this centrally-located 1600 square foot place. Located in the heart of Downtown Libertyville, half way between Chicago and Milwaukee. Close to Six Flags, Great Lakes Navy Base, Lake Michigan beaches, forest preserves, train station and the Chain of Lakes. Downtown Libertyville is a trendy town offering several restaurants, shops and fun events. Book one of the only units truly Downtown Libertyville.

PetsWalkabilityAccess

Popular amenities for Waukegan pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.95 out of 5 average rating, 104 reviews

A wooden deck steps lead to the entrance of a recently renovated home, framed by flower pots and outdoor seating. Decorative string lights are visible above, and an American flag is displayed on the left, adding to the welcoming atmosphere.

Home in Salem

Lago Amore - Channel house, pier, kayaks

Outdoor spacesPetsBathroom

4.84 out of 5 average rating, 103 reviews

The exterior of a single-story home is showcased with a spacious deck leading to a grassy yard. A large tree provides shade nearby, and the facade features clean white siding with several windows reflecting natural light.

Home in Round Lake Beach

Lake/Beach Getaway (Remodeled)

PetsWalkabilityDecor

4.81 out of 5 average rating, 113 reviews

The exterior of the lake house is visible, featuring a two-story design with a combination of light green siding and a dark roof. A spacious yard with autumn leaves leads down to the lake, showcasing a serene view of the water and trees.

Home in Ingleside

Lake house Monica Steps from the lake! 4BD 3bath

PetsOutdoor spacesHospitality

4.98 out of 5 average rating, 140 reviews

A modern house features an inviting front porch with landscaped gravel beds and well-maintained grass. A wooden garage door complements the green exterior walls. Surrounding trees and shrubs enhance the outdoor space, creating a welcoming entrance.

Home in Twin Lakes

4Bd 3.5ba Cozy New Construction! Close to lake!

WalkabilityPetsBathroom

4.97 out of 5 average rating, 118 reviews

A bright living area features a spacious cream-colored sofa with colorful pillows, complemented by a sleek console table with barstools. A large TV is mounted on the wall, while natural light enters through windows and glass doors leading to the outdoor patio.

Home in Highland Park

Modern Retreat near Ravinia & Botanic Gardens

Outdoor spacesPetsBackyard

4.9 out of 5 average rating, 30 reviews

Relax & Play! 9 Minutes from Naval Base Station

PetsWalkabilityIndoor spaces

4.78 out of 5 average rating, 51 reviews

Peaceful home in waukegan

QuietSleep qualityHospitality

A spacious living area is shown, featuring a comfortable sectional sofa and a decorative coffee table. The open layout leads to a modern kitchen, equipped with wooden cabinets and bar seating. A large dining space is visible in the background, enhanced by natural light from nearby windows.

4.96 out of 5 average rating, 55 reviews

Chic Oasis/Game Room/Near Base

PetsWalkabilityDecor

Pet-friendly home rentals with a pool

4.85 out of 5 average rating, 408 reviews

A winding red mulch pathway leads towards a charming A-frame house nestled among tall trees. The surrounding lawn is lush and green, with a peaceful natural setting enhanced by the canopy of leaves above.

Chalet in Ingleside

"A" Frame Brandenburg Lake

PetsOutdoor spacesLaundry

4.93 out of 5 average rating, 128 reviews

The modern kitchen features white cabinetry and a spacious island with four bar stools. A stainless steel refrigerator stands next to a gas stove and microwave. Natural light filters through large windows, illuminating the elegant countertops and sleek finishes.

Apartment in West Town

Cozy Duplex Down in Wicker Park East w/ Parking

PetsWalkabilityWi-Fi

4.75 out of 5 average rating, 303 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

Outdoor spacesWalkabilityGetting around

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.

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

Outdoor spacesPetsTV

4.87 out of 5 average rating, 168 reviews

4.98 out of 5 average rating, 90 reviews

A spacious indoor heated pool is seen, with clear blue water and steps leading in. Two lounge chairs are positioned nearby, and large glass doors provide a view of the outdoor area. Soft lighting enhances the calming environment.

Home in Grayslake

Family-sized Indoor Heated Pool & Movie Theater!

Outdoor spacesPetsTV

5.0 out of 5 average rating, 11 reviews

Condo in Fox Lake

4/2 Modern Luxury Home on Pistakee Lake with Pool

Outdoor spacesKitchenView

4.98 out of 5 average rating, 45 reviews

A well-maintained in-ground pool is shown surrounded by a concrete deck and lush greenery. A wooden fence encloses the yard, offering privacy. Tall trees and shrubs provide a natural backdrop, while the bright blue sky adds to the inviting atmosphere.

Home in Crystal Lake

Hot tub. Heated Pool. In town location.

Outdoor spacesPetsIndoor spaces

4.93 out of 5 average rating, 41 reviews

A log-sided home is set against a clear blue sky, overlooking a heated pool. Lush greenery surrounds the pool area and a spacious deck features seating and umbrellas. The house showcases large windows and a balcony that opens to the serene landscape.

Villa in McHenry

Fabulous Cabin

Outdoor spacesPetsAmenities

Private, pet-friendly home rentals

4.95 out of 5 average rating, 39 reviews

A modern living area features a gray sectional sofa and a round coffee table centered on a patterned area rug. A staircase with a dark wooden railing is visible on the side. A large piece of artwork brightens the wall, complemented by a tall potted plant.

Townhouse in Zion

Cute & Cozy, 1bd Condo Apartment/townhouse

PetsLocationSleep quality

5.0 out of 5 average rating, 77 reviews

The living room features a spacious sectional sofa in a soft gray tone, paired with a wooden coffee table. A large Smart TV displaying Netflix is positioned against the wall, while natural light enters through multiple windows, enhancing the cozy atmosphere.

Home in North Chicago

Gorgeous Home Stay | 4BD 1.5BA

Outdoor spacesIndoor spacesQuiet

4.82 out of 5 average rating, 45 reviews

Remodeled Waukegan Oasis | 4Bed 1.5Bath House NEW

PetsValueAccuracy

4.78 out of 5 average rating, 23 reviews

Home in Gurnee

Great America Getaway | Sleeps 12 | Near Navy Base

Outdoor spacesPetsBackyard

5.0 out of 5 average rating, 61 reviews

A screened-in porch features a seating arrangement with plush chairs and a central table. Natural light streams through the screens, offering views of the serene lake and surrounding landscape. A ceiling fan hangs above, providing a comfortable breeze in the inviting space.

Home in Trevor

Lakefront 2BR w/ Kayaks + Paddle Boards | Dogs OK

WalkabilityOutdoor spacesDecor

4.97 out of 5 average rating, 30 reviews

A spacious kitchen is equipped with wooden cabinets and modern appliances, including a refrigerator and stove. A central island with seating for three is visible, alongside a dining table. Natural light enters through multiple windows, enhancing the warm tones of the room.

Home in Libertyville

Home w/ porch in DT Libertyville Near Naval Base

PetsWalkabilityAccess

4.99 out of 5 average rating, 80 reviews

A spacious deck offers unobstructed views of the calm waters and nearby marina, where boats are gently moored. A grill and seating area provide a perfect setting for relaxation, surrounded by greenery and sunny skies.

Home in Kenosha

Waterfront w/Lake Views, walk to the beach!

WalkabilityPetsAccuracy