Holiday rentals in Highland Hills

Jacuzzi + Private Theater | Modern Getaway

Experience a unique Airbnb <5 min to Walmart, Target and Legacy Village shop mall <5 min walk to restaurants stunning 4-bed, 3-bath retreat in a friendly neighborhood. Discover local attractions & after relax in a stylish home featuring: Full Theater & hot tub 4 comfortable bedrooms with smart TV’s 1 Bedroom in main floor with full bath Spacious living & dinning area Game room includes Pool Table Fully equipped kitchen 6- Smart TV's with Wi-Fi Free Parking Embark on an unforgettable getaway!

The Worlds Cozy Nest

Rest and relax in this calm, stylish space. Sitting right in the heart of one of Cleveland’s most prestigious, safe suburbs, University Heights. This cozy home is Less than 15 minutes from Cleveland clinic and University hospitals main campus. Walking distance from plenty of shops and restaurants and less than 10 minutes from Legacy Village and Beachwood Mall, two of Clevelands premier, upscale shopping areas. This house has been newly renovated and comes equipped with all essentials plus more!

Modern & Peaceful Loft | Private Entrance

You’ll experience comfort and privacy in this renovated Shaker Heights studio, just minutes from Cleveland Clinic. Professionally designed for peaceful stays with a private entrance, $5k+ countertops, fridge & freezer, microwave, $1k+ queen bed, soft close cabinets, firm mattress, etc. Enjoy fast Wi-Fi, secure self check-in, perfect for medical visits, work trips. Located in a safe/historic neighborhood. Apartment is located on 3rd floor of a Tudor house, some stairs are required to access.

Modern Farmhouse Chagrin Falls Beachwood CVNP

Private Custom-Renovated Modern Farmhouse tucked into a wooded setting minutes from downtown Chagrin Falls and Hunting Valley. Neighboring Beachwood, Moreland Hills & Pepper Pike. 20min to Cuyahoga Valley National Park. Heated slate floors, spa like bath with endless hot water, dual work spaces & true privacy. Affectionately dubbed “The Wayback,” this home sleeps 6 with 2 private bedrooms, a fully equipped kitchen, and upscale amenities near Pinecrest & ETON dining, shopping, and entertainment.

Cozy 3BR | Relaxing Convenient Quiet Getaway

Just seconds from the highway, drive to visit nearby Cuyahoga Valley National Park, casinos, Cleveland Clinic, & University Hospital, & Pinecrest shopping. Welcome to this spacious, centrally located retreat in Bedford Heights—a quiet neighborhood less than 20 minutes drive to Downtown Cleveland, & outdoor adventures. Perfect for medical recovery, family fun, traveling professionals or extended stays-this space will make you feel right at home. Message for booking dates more than 60 days away.

Log Cabin I Nature's Oasis I Fire Pit + Gazebo

🌲 3 bedrooms • 4 beds • 1.5 bathrooms • Sleeps 6 🔥 Stone patio • fire pit • screened-in gazebo 🍳 Fully equipped kitchen • double ovens • eat-in dining 🪵 Log cabin vibes • nature views in every room 🪟 All-seasons room w/ game table + lounging area 🚗 Driveway parking for 5 cars + carport 📍 Next to Euclid Creek Reservation • 20 min to Downtown CLE Subtly tucked away, this mid-century log cabin offers peace, space, and a true connection to nature — all just minutes from Downtown Cleveland!

Trendy upscale retreat w/hot tub

Come relax in this calm, stylish space! Open floor plan on 2 very private acres- walking distance to village with large hot tub! Large open custom kitchen - fully stocked - great for family gatherings. De-stress in new Italian tile master bath. Award winning location, enjoy nearby wineries, arts, Cleveland’s best fine dining -located close to airport, sports & universities. Use our kayaks spending an afternoon on the nearby river, stroll thru the village or relax in our tree lined yard!

Upscale 2Br Near Van Aken/Hospital/CWRU (2nd FL)

This newly renovated 2BR 1Bath home is located in a safe, peaceful and friendly neighborhood in the heart of Shaker Heights. Our home offers great convenience and is surrounded by the area's best shopping and dinning - walking distance to Heinen's and CVS; 5 minutes to Van Aken District; 10 minutes to Beachwood and Pinecrest; 15 minutes to Cleveland Clinic, UH, University Circle, Orchestra, Art Musem; and close to major employers. It is situated near public transportation, I-271 and I-480.

Cozy Home, Ideal for Travel Nurse in NE Summit Co.

Enjoy a stay in our newly remodeled 1850's home nestled in the corner of Summit County overlooking 9 acres of field and white pines. This duplex is a single level home with a private entrance for our Airbnb guests. Conveniently located near I-271/I-480 and less than 5 miles from MGM Northfield Park. Restaurants, shopping, and Summit County Metroparks are just a short drive away. Enjoy a hike and gorgeous scenery in Ohio's own Cuyahoga Valley National Park within a 10 mile drive.

Cozy Quiet Ranch with Sprawling Yard

This cozy ranch has undergone a complete renovation and sits on a quiet street that dead ends into the Metro Park bridle trails. This unit features comfortable furnishings, all new stainless steel kitchen/laundry appliances, and comes with a huge back yard that frequently gets visited by wildlife. This house is only a 10-15 min walk from Bedford's historical district that has been featured in Architectural Digest as one of the top 30 most beautiful main streets in America.

Star Wars–Themed Home w/ Arcade | Family-Friendly

Enjoy your stay at a newly updated Star Wars–themed family home- perfect for relaxing getaways, extended stays, or families needing comfortable temporary housing nearby. 📍 Nearby: • Cleveland Clinic – 20 min (medical stays & visits) • Pinecrest – 6 min (dining & shopping) • Cuyahoga Valley National Park – ~20 min (trails & scenic railway) • Downtown Cleveland – ~20 min (museums & sports) • Hopkins Airport – 20 min (easy travel access) 🚭 Smoke-free & pet-free home

Little Black Cabin in the woods

We have a 900 sq.ft. , log cabin in the woods. The woods of Solon, OH. A southeast suburb of Cleveland. The cabin has 2 bedrooms, each with a queen bed and lots of built in cabinets. They share full bath. As you enter the mud room, to the right is a laundry room with washer & dryer, straight ahead the great room complete with a stone fireplace lots of windows and a small functional kitchen. Welcome to your home in the woods!!