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!

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.

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.

Tennis House

Enjoy this wooded corner lot retreat with private tennis court during the day or under the lights. New kitchen and mid mod renovated main floor. 3 bdrms, 2.5 baths, and laundry. Quirky home also boasts a Japanese tea garden in back, a full English pub in the lower-level walk out, and a gazebo. Located 2 min to Gates Milles, 8 min to Hillcrest Hosp, 12 min -Chagrin Falls, 25 mins -Cleveland Clinic, and 32 mins to downtown CLE great for ball games, weekend visits, and family time.

Cozy Heights Oasis-Walk to Restaurants

Private and cozy second floor 2 bedroom spacious unit in the Cedar-Lee district of Cleveland Heights. Completely refurbished. Walk to restaurants on Lee Road or Cain Park. Open the windows and listen to a chorus of birds-a true oasis from the hub-bub. A private patio and outdoor living right off the living room. Note: Quiet hours after 10 p.m. This unit is not suitable for partying, loud music and disruptive behavior that impacts neighbors or guests in other apartments.

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 Abigail House

Welcome to The Abigail House — a beautifully renovated, family-owned short-term rental nestled in the heart of Cleveland’s east side suburbs. Thoughtfully designed, this 1,600 sq ft first-floor apartment offers a peaceful retreat inspired by our travels and deep hometown roots. Whether you’re a traveling professional, visiting small family, or simply seeking a peaceful getaway, you’ll find everything you need within reach, from local eateries to cultural attractions.

Maple Heights 3BR Summer Haven — Cozy & Spacious

Welcome to your cozy home away from home! This bright and beautifully furnished house offers the perfect mix of comfort, style, and functionality. Whether you’re visiting for work, family time, or a peaceful getaway, you’ll find everything you need right here. Ideal for couples, solo travelers, families, or business trips. The house is fully stocked with everything you need for a short getaway or a long-term stay, just bring your suitcase and make yourself at home😎

Cozy Stone Castle 12 min to CWRU!

Private & cozy 2 Bedrm apt in a stone castle style home is 4.1 miles, only 12 min, to Clev Clinic/CWRU. Fab hardwood floors, upscale furnishings and elegant chandeliers. Popular location near universities, hospitals, shopping districts and restaurants. This unit is on the lower level and features an office space with an extra thick n plush futon sofa bed in the 2nd bedroom! Significant discounts for weekly and monthly stays.

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!!

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.