Holiday rentals in Highland Hills

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.

Rock 'n' Roll Retreat ~15min to DT~8min Cle Clinic

Unwind in this newly renovated 2BR 1Bath Rock n' Roll retreat in a friendly & vibrant Larchmere neighborhood just 15 mins from the Rock 'n' Roll HOF. This 2nd floor apartment offers a relaxing getaway near restaurants, shops, attractions, landmarks, and major hospitals and employers, making it ideal for your stay in the Cleveland area. ✔ 2 Comfy Bedrooms w/ Queen-Size Beds ✔ Central Air and Heat ✔ Fully Equipped Kitchen ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Parking See more below!

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.

Hot Tub + Game Room + Fenced Back + EV + Pets OK + Kings + Kid Loft

Summer Specials! Gather family or friends for an unforgettable getaway in a spacious, pet-friendly, amenity-rich oasis in a quiet neighborhood. You’ll find fun and relaxation at Serenity At Seven Hills with its loaded gameroom, games, hot tub, Jacuzzi tub, fenced yard. You’ll love the proximity to Cleveland and the garage parking and EV charger. Guests rave about host responsiveness; one guest called it “Best Airbnb we have stayed in.” Contractors - Traveling Workers - Families Welcome

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

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!!

“BOOK NOW”- Pool Closing! Last Chance for Summer!

Nestled in a peaceful rural setting, this fully appointed upscale cabin rests on a breathtaking property in a lush valley. Scenic wooded trails meander along the West Branch of the Cuyahoga River, offering a tranquil escape into nature. Panoramic views showcase rolling hills, a serene, elevated porch view, vibrant seasonal foliage, towering pines, and abundant wildlife-creating a truly unforgettable retreat.

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

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.

Fabulous Fairmount Retreat

Enjoy a charming, sunny home located in the heart of The Heights across from an acclaimed French bakery and buzzing Parisian style bistro. Walk to shops or the Shaker Lakes. Perfect spot for visits with family, or access to local universities, the Cleveland Clinic or University Circle museums and cultural institutions.