Holiday rentals in Highland Hills

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!

Quiet Cozy 3BR | Relaxing Convenient Getaway

Just seconds from the highway, drive to visit nearby Cuyahoga Valley National Park, Pinecrest shopping, casinos, Cleveland Clinic, & University Hospital. 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 property will make you feel right at home. Message for booking dates more than 60 days away.

The Lake House

** We do not allow weddings (including “micro”), parties, or events of any kind. ** 10 minutes from downtown! DIRECTLY on Lake Erie's shoreline, cantilevered above the water. Completely private waterfront escape. Experience the sound of the waves for a truly relaxing getaway. THE VIEW - Panoramic views of Lake Erie and surrounding wildlife. Dreamy sunsets. THE INTERIOR - The meticulously designed interior blends the timeless charm of mid-century modern architecture with high-end luxuries.

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, in a safe/historic neighborhood. Apartment is located on a 3rd floor of a Tudor house, some stairs are required to access.

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

The Mill House

The Mill House, built in 1890, sits in downtown Chagrin Falls, a former mill town with a history of 9 mills powered by the Chagrin River. Settlers in the mills' early days lived in the village's old homes, inspiring the name "Mill House." Nearby, you'll find restaurants, coffee shops, stores, a grocery, pharmacy, the famous popcorn shop, waterfalls, and the historic Chagrin Falls Hardware. We only accept guests that have reviews.

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!!

The Maproom Room | 10 Mins to Cleveland Clinic, UH

🗺️ Map-themed studio • Sleeps 2 ✨ Fully renovated • Clean + modern ☕ Kitchenette • Coffee maker • Microwave & Instapot 📺 Smart Roku TV + streaming apps 🚗 Off-street parking for midsize cars (1 spot) 📍 10 min to Cleveland Clinic + University Circle Modern comfort meets world travel charm in this map-inspired studio apartment — thoughtfully designed and ideally located near Cleveland’s best cultural attractions.

Maple Heights Serenity

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!

[C] Sky Light | Cozy 1BR Apt, TOP | Coventry Area

Welcome to our modern 1-bedroom city apartment, situated just a short distance from the vibrant downtown area. Relax in the comfortable living room and enjoy the convenience of being close to the city's attractions without the hustle and bustle right at your doorstep. Our apartment is ideal for couples or business travelers looking for a comfortable and well-located 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.