Pet-friendly vacation rentals in Highland Park

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Top-rated pet-friendly home rentals in Highland Park

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in McHenry

4.93 out of 5 average rating, 126 reviews

Riverside Retreat : A Nature Lover’s Dream!

Immerse yourself in nature at this enchanting 3bedroom cabin! Discover adventure-ready luxury in our historic 1950s riverside home. Unwind in the outdoor spa tub or challenge friends in the game room. Your gateway to riverside bliss with a private boat dock. Bring water toys and enjoy access to the Chain of lakes. Explore Moraine State Park's outdoor wonders just steps away. Indulge in downtown McHenry's dining and nightlife options. Escape to perfection in this one-of-a-kind handcrafted cabin.

Guest favorite

Cabin in Lake Geneva

4.98 out of 5 average rating, 197 reviews

Charming A-Frame - Dog Friendly!

FEATURED IN Madison Magazine's, December 2021 issue, "Wisconsin Winter Cabin Getaway"....The River Birch Cabin is a 900 sq ft A-Frame nestled in a partially wooded lot and is the perfect couples retreat or family escape from the city. Just 2 blocks from Lake Como, there are many activities & restaurants nearby including kayak & boat rentals. It is also located within minutes of Lake Geneva Ice Castles/Winter Realms, plus fishing, hunting, hiking, ziplining, snow skiing, boating & much more.

Superhost

Rental unit in Park Ridge

4.79 out of 5 average rating, 404 reviews

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment

Guest favorite

Condo in Skokie

4.91 out of 5 average rating, 104 reviews

Parking Terrace Near Universities Up to 20%OFF

LUXURIES 2 BEDROOMS, 1 BATH APARTMENT WITH LARGE FURNISHED BALCONY. FREE PARKING NEXT TO THE ENTRANCE. BRIGHT & SUNNY SOUTHWESTERN EXPOSURE. THIS CORNER UNIT IS LOCATED ON THE FIRST FLOOR-FEW STEPS UP. QUIET PROPERTY IN RESIDENTIAL AREA. MODERN KITCHEN WITH NEW STAINLESS STEEL APPLIANCES. KEURIG COFFEE MAKER. CENTRAL AIR & HEATING, HARDWOOD FLOORS, FAST WI-FI INTERNET, LARGE 55" ROKU TV, FREE LAUNDRY. SPARKLING CLEAN APARTMENT. BOOK IT WITH CONFIDENCE YOU WILL ENJOY STAYING HERE, I PROMISE YOU.

Superhost

Rental unit in Highland Park

4.86 out of 5 average rating, 99 reviews

Chic Studio in Downtown Highland Park near Metra

Welcome to downtown Highland Park! Experience comfort and convenience in our cozy studio apartment with FREE parking. Just a 5-minute walk to the Metra, and within a leisurely 15-minute stroll, enjoy breathtaking views of Lake Michigan. Explore historic Fort Sheridan Forest Preserve and beach, only a quick 5-minute drive away. Discover delightful dining, gelato shops, parks, and more—all within walking distance. Our well-appointed apartment ensures a memorable stay in this vibrant neighborhood.

Guest favorite

Rental unit in Highland Park

4.93 out of 5 average rating, 149 reviews

Lovely studio near the beach! (and heated floors!)

Get away from the city to this studio in Highland Park. The newly renovated space has everything you need for a relaxing getaway—huge comfy couch, brand new bed with Brooklinen + Parachute bedding, pristine bathroom, and lots of amenities. Downtown Highland Park, Highwood, + the beach are just a walk away. There's access to grocery stores, restaurants, and shops, and you can retreat to the quiet of your studio when you're ready to unwind. Ps. For the winter months: We've got heated floors.

Guest favorite

Home in Highland Park

4.91 out of 5 average rating, 140 reviews

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

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Guest favorite

Home in Richmond

4.96 out of 5 average rating, 138 reviews

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 !

Guest favorite

Home in Lake Geneva

4.88 out of 5 average rating, 210 reviews

Beautiful Home w/ Hot Tub in Lake Como, Wisconsin

Enjoy time with friends and family in this fully equipped 2 bedroom 1 bathroom home in the great neighborhood of Lake Como. Our house is located 1.5 blocks from the lake and is less than a 10 minute drive to Lake Geneva. Featuring an outdoor hot tub, gated backyard and an amazing basement bar. Spend the afternoon shopping and enjoying the many activities the area has to offer. Spend the evening with a cocktail in the 4 person hot tub on the deck or have some s'mores by the firepit.

Guest favorite

Guest suite in Naperville

4.95 out of 5 average rating, 375 reviews

Lake facing cozy little studio with private entry

This is a luxurious cozy little studio facing the lake, featuring a private entrance that is attached to a single family home. The studio is equipped with a top quality queen bed, an in-suite kitchenette including a mini fridge, microwave, and induction top, as well as a luxurious full bathroom. The studio is situated in the safest and friendliest neighborhoods in Naperville conveniently located close to cafes, restaurants, markets, a biking trail, and just minutes away from I88.

Guest favorite

Rental unit in Libertyville

4.88 out of 5 average rating, 136 reviews

131 East Park Ave. #308

Keep it simple at this peaceful and centrally-located apartment walking distance to fantastic downtown Libertyville. Very nicely maintained building with elevator. 7 miles to Great Lakes Naval Base. Super clean unit with all brand new furnishings. HD smart TV's with cable in both the living room and bedroom. Pull out bed in living room good for one person. Fast Wi-Fi with dedicated work desk. Ample free parking right in front of the building. On-site laundry one floor down.