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!

High Road Retreat

Welcome to our sweet retreat! My daughter and I have created a cozy space where you can feel right at home! This newly renovated, entire home with 2 bedrooms, is conveniently located just outside of Cleveland, and a short 5-minute drive from the highway in a quaint and quiet neighborhood. Whether you’re traveling for a music concert, sporting event, exploring the city, discover our vast hiking trails, require a place if a loved one is in hospital, or a traveling nurse, we are centrally located!

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.

Quiet Cozy 3BR | Relaxing Convenient 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.

Rare Cleveland Apt: Little Italy! W/Sauna&Hot tub!

Fall in love with this charming, newly updated 1-bedroom, 1-bath lower unit triplex apartment situated in the heart of Little Italy, walking distance from University Circle, UH Hospital, Cleveland Museum of Art, Botanical Garden, Public Transportation and much more. Apartment is complete with a well-equipped kitchen, Smart TV, laptop workspace, and modern furnishings, this vacation/business rental delivers all the essentials so you can spend more time relaxing and exploring.

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

Home Away From Home - Beautiful Yard

Welcome to South Euclid! This the perfect single family home to escape from the hustle and bustle of the city. Enjoy quiet streets, a nice large patio where you can sip your morning coffee and a comfortable sectional to spread out with the whole family or friends to watch TV or just chat about the day. Traveling with pets? No problem! We are pet friendly and would love to host your furry friends! Don't miss out on this 3 bedroom 1 bath today!

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!!

Historic District - Fully Stocked Kitchen-Sleeps 6

Enjoy a comfortable stay in this inviting Bedford duplex! You’ll be booking one side of a charming duplex home, giving you a private space to relax while still being part of a side-by-side property. With a fully equipped kitchen, coffee bar, and comfy living room. Features a king, two queens, Smart TVs, office space, laundry, and parking. Close to Bedford Reservation, waterfalls, and Cuyahoga Valley National Park.