
Family-friendly holiday rentals in Willoughby
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Willoughby
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Charming Relaxing Cozy Lake Erie Getaway Cottage
A charming and quirky 1930’s cozy lake cottage bungalow recently remodeled with over 900 sq ft plus an adorable sunroom lined with windows. Enjoy the private fenced backyard oasis with waterfall and garden pond. Includes your own long driveway, perfect for car and boat parking plus 2 extra spaces. Provided is a variety of entertainment including air hockey table, puzzles, Atari, Roku, BluRay DVD player, & board games. Located on a quiet street that dead-ends into the Mentor Harbor Yachting Club.

Lake Erie Getaway
Enjoy the wondrous beauty and sunsets of Lake Erie, the 11th largest freshwater lake in the world. From the back yard you can swim or fish. 2 bedroom/2 bathroom house with cozy electric fireplace in family room . 1300 square feet of first floor living on Lake Erie.Lake views from nearly every room. Private fenced backyard with over 400 plants. Twenty minutes from downtown Cleveland and University Circle area, 10 minutes to downtown Willoughby and a 5 minute walk to the grocery stores and deli

Retreat at DTW
Come relax & enjoy The Retreat at DTW! Just minutes away from Historic Downtown Willoughby where you can shop, dine & stroll the streets at your leisure. This completely renovated single family ranch home has so much to offer. Including all kitchen appliances, washer & dryer, all necessities (kitchenware, towels, sheets, etc.) & playing cards plus board games for your pleasure. The bedroom has a king bed & living room has a sofa bed. Enjoy the reading nook on the 2nd level loft area & backyard.

Lake House with Amazing Views
Amazing location right on Lake Erie. This cozy lake house has a large kitchen, full bathroom and a living room/bedroom with king-size bed. The cottage is off by itself so you can enjoy your seclusion, but we live about 200 feet away so we can assist you if you need us. Enjoy a morning coffee on the deck while watching nature, spectacular sunsets on the private patio, and falling asleep to the sounds of the lake. You will be blown away by the beauty and peacefulness of this amazing cottage.

Lovely 2 bedroom 1 bath ranch, fully equipped.
Welcome to The Stone House! Keep life comfortable and simple at this beautiful ranch. This charming home is exceptionally well located a short drive away from many of Cleveland’s most exciting attractions including all of the sports stadiums, the Rock and Roll Hall of Fame, Amazon, and Cleveland Clinic. We respond to booking inquiries within 1 hour (if request received between 8 a.m. -10pm ET)! No smoking, no pets, no events, no parties. READ THE RULES BEFORE YOU CONTINUE WITH YOUR REQUEST.

Upscale-Lakefront-Private Beach-Hot Tub-King-Pets
Lakeside living at its finest. This amazing oasis is comfy and inviting with stunning views, expansive deck, and your own private beach. Fully renovated, carefully curated and meticulously cleaned-this indulgent gem is perfect for a serene dip in the hot tub at sunset or easy fishing from the shore. Relax and watch the boats, eagles and waves-everything has been thought of here. Your spacious master suite looks out over a second-floor balcony. A perfect place to enjoy the in-room coffee bar.

Chardon Loft
Large private 2nd floor studio style living area with queen size bed, couch, table/chairs, TV, refrigerator, microwave, hot plate, NO OVEN OR STOVE TOP, sink, large shower, A/C, heat, washer and dryer, and deck. Wifi internet is provided. The television has Netflix. No cable channels. The furnace is nontraditional. It is not located in a closet. The noise when running and starting will be louder than normal during winter months. Ear plugs are available for those that are noise sensitive.

Lydia's Lake Erie Cottage
In the heart of Willoughby, a cozy cottage awaits you as the perfect getaway spot. Situated on the shores of Lake Erie, you'll be able to enjoy stunning lake views on the water's edge. Inside, you'll find a cozy and well-appointed space, complete with a fully stocked kitchen and outdoor grill, Unwind by the fireplace in the living room or catch up on your favorite shows on the smart TV. Stay connected with the free WiFi, and take advantage of the laundry with a washing machine and dryer.

Residential Apartment w/Drumkit
Quiet apartment in residential neighborhood attached to owner occupied home. Beautiful scenic large backyard with dining area & fire pit. Electronic Roland, TD-8 drum kit to be enjoyed by everyone: If you’ve ever wanted to play the drums and haven’t had a chance, or if you are a current player looking to keep your chops in shape!! Located 25 min. from Cleveland with a beautiful Great Lake (Erie) at the end of the st.&Lakefront Lodge Park 1/2 mi. Many food/grocery establishments nearby.

Lakefront Home
Peace and tranquility await in this charming bungalow with lake views (NO LAKE ACCESS) at every direction. Just a few feet from Lake Erie, this gem has 2 bedrooms and 1 bath with a delightful interior design that is a mix of midcentury modern and contemporary décor. Situated at the end of a private drive, it has a washer/dryer (for stays greater than +4 days), fully equipped kitchen, off-street parking, 2 TV’s, work desk and internet (NO CABLE). NO PETS OF ANY KIND & NO FISHING

The Nest! 2 bedroom
Welcome to our charming 2 bedroom 1 bathroom unit, where comfort meets convenience! Nestled within walking distance (.03miles) from Historic Downtown Willoughby, our stylish and spacious accommodation offers a delightful retreat for your stay. With thoughtful touches, modern amenities (Smart TV's, Keurig), and proximity to local attractions, such as dining, shopping, and the local nightlife! We guarantee a memorable experience during your time here.

1 BR WiFi Downtown Willoughby self check in Unit A
Quaint 1BR walking distance to Downtown Willoughby. Enjoy the added touches like smart TVs in the living room and bedroom. The bathroom is small so please take a look at the pictures. A kuerig coffee machine for that morning cup of coffee. A rain head shower head in the “claw” tub and shower. Perfect for a quick getaway to enjoy the downtown willoughby area.
Popular amenities for Willoughby family-friendly rentals
Family-friendly home rentals with a hot tub

Sandstone Ranch

Cozy winery getaway with hot tub!

Cozy A-Frame Getaway Minutes from Nelson Ledges

Wine Country Oasis with Pool & Hot Tub

Cheerful Cabin-Sleeps 5 - lake views + relaxation

Hot Tub, CVNP, Private Waterfall Trail, Firepit

Groovy Cedar Chalet Forest View

Mahoning River Lodge Unique Grain Bin w/ hot tub
Family- and pet-friendly home rentals

Mid-Century Modern Ranch in quiet neighborhood

Sunny Studio II / Private home next to Ray's MTB

Chagrin Falls Charmer

Cozy Cottage, Modern Amenities

Cozy house near Lake Erie, 10 minutes to Downtown.

Unique Farm Stay -Brandywine Falls -Peaceful CVNP

Abby's Tranquil Lakeside Cottage

Cozy Solar Powered Hideaway (Pet Friendly)
Family-friendly home rentals with a pool

Euclid Escape - Poolside Bliss with Hot Tub

Stillwater Retreat-Waterfall·Pond Horses·Firepit

Lake Erie Condo #108 w/ amazing view & indoor pool

Madison on the Lake Home w/ pool in wine country!

Your home away from home!

Cozy | SPIRE | Winery Tours | GOTL | Beach

Boho Star Pad on Madison-beautiful & cozy 1 bd rm

the Black Barn Guest House
When is the best time to visit Willoughby?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $178 SGD | $192 SGD | $201 SGD | $169 SGD | $174 SGD | $184 SGD | $204 SGD | $208 SGD | $195 SGD | $190 SGD | $199 SGD | $216 SGD |
| Avg. temp | -2°C | 0°C | 4°C | 10°C | 16°C | 21°C | 24°C | 23°C | 19°C | 13°C | 7°C | 1°C |
Quick stats about holiday rentals that are family-friendly in Willoughby

Total holiday rentals
Explore 30 holiday rentals in Willoughby

Nightly prices starting at
Willoughby holiday rentals start at $89 SGD per night before taxes and fees

Verified guest reviews
Over 2,010 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Willoughby holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Willoughby rentals

4.8 Average rating
Willoughby stays are highly rated by guests – averaging 4.8 out of 5!
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- Cuyahoga Valley National Park
- Rocket Mortgage FieldHouse
- Progressive Field
- Rock & Roll Hall of Fame
- Cleveland Browns Stadium
- Headlands Beach State Park
- Mosquito Lake State Park
- Little Italy
- Cleveland Metroparks Zoo
- Punderson State Park
- Case Western Reserve University
- Boston Mills
- Cleveland Museum of Natural History
- Cleveland Botanical Garden
- Laurentia Vineyard & Winery
- Agora Theatre & Ballroom
- Cleveland Museum of Art
- Debonné Vineyards
- Crocker Park
- The Arcade Cleveland
- JACK Cleveland Casino
- Huntington Convention Center of Cleveland
- Rocky River Reservation
- Stan Hywet Hall and Gardens





