Holiday rentals in Highland Hills

Top guest favourite

Guest favourite

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.

Luxurious Hidden Gem in Suburbs of Cleveland OH

Welcome to a luxury getaway! Nestled in the quaint community of Gates Mills, this spectacular 4 bed/4.5bath modern estate offers style, open-concept living, and peaceful privacy. This home features high ceilings and panoramic windows that overlook a beautiful wooded lot, and offers a true country setting without sacrificing urban convenience. Large private driveway to park. Local Metroparks hiking and biking trails just minutes away. Conveniently located just 30-minutes from downtown Cleveland.

Top guest favourite

Guest favourite

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.

Leather Recliner | FREE Garage Parking | Updated

Step into comfort and style in this beautifull home. Unwind after a long day on the luxurious leather reclining sectional, perfect for cozy evenings or movie nights. With six plush beds, restful sleep is guaranteed for every guest. Each room is designed with your comfort in mind, with a desk, chair, TV, chest of drawers, and other furnishings to make your more convenient. Whether you're here for work or leisure, this home offers the perfect blend of comfort and tranquility.

Top guest favourite

Guest favourite

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

Sleeps 3 | Cleveland Clinic + University Circle

Chic Studio in Prime Location — Steps from Cleveland’s Best Experience the city right at your doorstep. This modern open-concept studio is ideally located near University Circle, Cleveland Clinic, top museums, Little Italy, and just minutes from Downtown Cleveland, major stadiums, and popular attractions. Features Cozy sleeping area Fully equipped kitchen Clean, modern bathroom High-speed Wi-Fi In-unit washer and dryer Free private parking included

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.

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!!

Family Retreat | Sleeps 12 + Fenced Yard

🏡 Spacious family home in quiet University Hts 🛏 4 Bedrooms • Sleeps up to 12 🐾 Pet-friendly with a fully fenced backyard 👶 Family-friendly w/ high chair & board games 🔥 Fire pit + outdoor dining 🎯 Game room, foosball & dartboard 🍳 Fully stocked kitchen 📺 Multiple Smart TVs + fast Wi-Fi 📍 Minutes to John Carroll, hospitals & downtown Cleveland

Top guest favourite

Guest favourite

Cozy Mid-Century Modern University Heights Getaway

Welcome to our meticulously re-imagined mid-century modern space, where relaxation and style harmoniously come together. This property has undergone a complete top-to-bottom renovation, ensuring that every aspect is refreshed and revitalized. With plenty of space to unwind and recharge, you can truly kick back and enjoy your stay.