Holiday rentals in Highland Hills

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.

Stay at Supreme!

Enjoy a comfortable and convenient stay in the heart of Beachwood. Located just minutes from Cleveland Clinic and University Hospitals, beautiful parks and nature trails, and top shopping and dining at Pinecrest and Eton Malls, our home is perfectly situated for both short and extended stays. The house is minutes from local synagogues and kosher restaurants. A spacious, fully renovated home, with a modern touch. It’s an ideal place to relax and feel at home—no matter the reason for your visit.

Cozy Apartment in Charming Village

Cozy apartment with private entrance attached to historic house. Central location in this charming tourist village of Chagrin Falls, a short walk to the natural waterfalls, over 20 great restaurants, two ice cream shops & boutique shopping. Low ceilings & compact bathroom, but full kitchen and parking for one car. Non-smokers only. No pets - out of consideration for future guests. Guests must be able to climb stairs to access apartment. Air conditioning is available during the summer season.

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.

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

Gallery House | Near Clinic + Museums

🎨 Artist-curated apartment • Sleeps 4 🛋 Decorated w/ works by local artists (for sale!) 🛏 2 bedrooms • 1 bathroom ✨ Modern & bright 📍 Minutes to Cleveland Clinic, UH & CWRU 🎶 Walk to dining, bars, shopping & Cleveland Orchestra 📺 Smart TV w/ streaming apps 🚗 1 mid-sized off-street parking spot + free street parking Stay in style and surround yourself with Cleveland’s creative spirit — a one-of-a-kind apartment curated by local artist Dawn Tekler.

5-BR Colonial, King Bed, Main Floor BR, Pool Table

🏡 Enjoy a spacious two-level, 5-bedroom home perfect for families, medical visits, business travel, and extended stays. The main floor offers: A queen bedroom A half bath Upstairs includes: Four bedrooms Two full bathrooms Relax with: A king bed A pool table A foosball table A 58-inch living-room TV A 50-inch primary-bedroom TV Fast Wi-Fi A workspace A full kitchen Laundry Self check-in Parking Sleeps up to 12 registered guests.

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!!

Maple Heights Oasis

Conveniently situated near Cleveland, this place offers both comfort and easy access. Just a short drive to downtown, the airport, Edgewater Beach & Lake Erie. Close to shops, restaurants, parks, and family fun centers. Features a modern kitchen, Wi-Fi, and a SMART TV (log into your own Roku). Shared washer/dryer (paid use). No cable; don’t forget to log out before checkout. A great spot for work or relaxation!

Spacious house in University heights

This is a spacious, fully updated single-family home in a quiet University Heights neighborhood, comfortably accommodating up to 10 guests. Designed to be a reliable, and stress-free home base near John Carroll University, University Circle, and the Cleveland Clinic, the property features a dedicated basement gym, a quiet outdoor patio, and a finished attic equipped with a lounge, TV, and foosball table.

Luxury|Pool Table|Movie Room|Poker|Nature Oasis

Escape to luxury in this 4-bedroom, 3.5-bath home featuring a spacious living room, dining area, and fully equipped kitchen. Enjoy a home office, lower level with games and movie room, and a master suite with private bath. Outside, explore a nature-filled backyard with a walking trail, creeks, and fire pits. Ideal for relaxation and fun, this home blends modern comfort with stunning outdoor beauty.

Pet-Friendly 3BR Retreat Near Cleveland

🏡 Comfortable 3BR home in quiet South Euclid 🛏 3 Bedrooms • Sleeps up to 6 🐾 Pet-friendly 🌿 Large yard + spacious patio 🛋 Comfortable living room w/ large sectional 🍳 Updated, fully equipped kitchen 📺 Smart TV + fast Wi-Fi 🚗 2-car garage + additional street parking 📍 Convenient to Cleveland Clinic, University Circle & downtown