Vacation rentals in Highland Hills

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Top-rated vacation rentals in Highland Hills

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Guest favorite

A modern living area features a comfortable sofa with cushions, two cozy armchairs, and a coffee table. Large windows allow natural light to fill the room, enhancing the neutral color scheme and contemporary decor. A television stands on a sleek entertainment unit, completing the inviting space.

Apartment in Shaker Heights

4.93 out of 5 average rating, 166 reviews

Modern & Comfy ~ Close to CLE Clinic ~ Long-Stays!

Unwind in this newly renovated 2BR 1Bath modern-industrial oasis in a friendly & vibrant Shaker Heights, OH neighborhood. This 2nd floor apartment offers a relaxing getaway near restaurants, shops, attractions, landmarks, and major hospitals and employers, making it ideal for traveling nurses and business travelers looking for an extended stay. ✔ 2 Comfy Bedrooms w/ Queen Beds ✔ Relaxing Living Area ✔ Fully Equipped Kitchen ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Parking See more below!

Top guest favorite

A spacious living area features a leather couch with decorative pillows and a light wood coffee table. Natural light enters through a window near the staircase, while a mounted television and decorative fireplace accentuate the cozy atmosphere.

Home in University Heights

4.9 out of 5 average rating, 105 reviews

Stylish&Bright 4BR w/Sun Deck-Close To Everything!

Cute & cozy, this recently updated 1930's house this full of classic charm and close to EVERYTHING! Fully furnished with brand new, modern furniture & fixtures, central A/C, 100% cotton bedding, and all of the amenities you need to make this place your home away from home. Walk to Whole Foods, Starbucks, Target, JCU, parks, coffee shops, restaurants and retail, public transportation. Short drive to Cleveland Clinic, UH, museums, downtown CLE, West Side Market, sports & entertainment districts.

Guest favorite

A bright three-season porch is furnished with two wooden chairs and a small coffee table. Natural light fills the space, and a plant sits on a side table. A textured area rug covers the floor, enhancing the casual and inviting atmosphere.

Apartment in Shaker Heights

4.88 out of 5 average rating, 67 reviews

Quiet Cleveland Retreat • Fully Stocked • Comfy Be

Peaceful • Convenient • Perfect for Extended Stays Whether you’re here for medical visits, remote work, or family time, this quiet Shaker Heights duplex is designed to help you feel right at home—just 15 minutes from Cleveland Clinic and downtown. 💰 Long-Stay Discounts • Stay 7+ nights: Save 10% • Stay 28+ nights: Save 25% Step into comfort with: • Secure keyless entry and digital locks on all doors • A cozy, fully stocked kitchen • Fast Wi-Fi + a dedicated workspace • A peaceful three

Top guest favorite

A bright living room features a cozy orange sofa paired with two armchairs adorned with patterned cushions. A wooden coffee table sits in the center, complemented by a decorative rug. Natural light filters through the windows, enhancing a welcoming atmosphere.

Apartment in Cleveland Heights

5 out of 5 average rating, 175 reviews

The Farmhouse - 1 Bdrm Apt in a Great Location

Welcome to this 2nd flr 1 bd/1 ba private apartment in a charming 1880s farmhouse located in a friendly walkable neighborhood. Full kitchen with all you need to make your own meals, washer/dryer and separate office inside the unit. Free off-street parking. You are only: 5 min walk to Starbucks, a variety of restaurants, bars, shops, trails 5-10 min drive to Cleveland Clinic, University Hospitals, Case Western, museums, parks, Little Italy and more 15 min drive to major attractions and Lake Erie

Guest favorite

A cozy living area features two black chairs and a beige sofa, complemented by a circular glass coffee table. The walls are painted white, creating a bright atmosphere, while the sloped ceiling adds character. A small kitchenette is visible in the background.

Apartment in Shaker Heights

4.91 out of 5 average rating, 136 reviews

Small and Cozy 1BR Near Cleveland Clinic~Safe Area

Relax in this newly renovated 1BR 1Bath unique efficiency in a friendly, safe & vibrant Shaker Heights, OH neighborhood. This upper level unit offers a relaxing getaway near excellent restaurants, shops, attractions, landmarks, major hospitals and employers, making it ideal for traveling nurses and business travelers looking for an extended stay. ✔ Comfy Bedroom ✔ Relaxing Living Area ✔ Basic Kitchenette ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Air Conditioning ✔ Washer/Dryer ✔ Parking See more below!

Top guest favorite

A cozy bedroom features a queen-size bed with a light green coverlet. Decorative floral prints adorn the walls. A bedside lamp and a wooden nightstand are positioned nearby. A sliding mirrored closet door reflects the space, adding depth to the inviting atmosphere.

Apartment in Chagrin Falls

4.97 out of 5 average rating, 589 reviews

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.

Superhost

Apartment in Cleveland

5 out of 5 average rating, 3 reviews

Rooftop | Free Parking | Near Cleveland Clinic

✨ Discover comfort & convenience in our charming city haven! Perfect for professionals & travelers, this apartment is your gateway to nearby dining, universities, museums, shopping, & top attractions. 🌟 Amenities 🍳 Fully Equipped Kitchen – Cook with ease! 🛏️ Cozy Bedroom – Comfy bed for a restful night’s sleep. ♿ Handicap-Friendly Bathroom – Safety handle bars. 🌆 Rooftop Patio – Unwind in city vibes. 🧺 In-Unit Washer/Dryer – Laundry made simple. 📶 Complimentary Wi-Fi – Stay connected.

Superhost

A cozy living area is showcased with a light-colored sofa, a modern television on a white entertainment unit, and a decorative plant. Natural light enters through the windows, while the textured brown wall adds warmth. Soft carpeting enhances the comfort of the space.

Apartment in Cleveland

4.78 out of 5 average rating, 18 reviews

Beige lovely 1 bedroom unit

Welcome to our unique Airbnb nestled in the heart of a vibrant, culturally rich neighborhood. Immerse yourself in the authentic charm of our black developing community, where you'll find a warm and inviting space that's more than just a place to stay – it's an experience. This tastefully designed Airbnb offers a blend of modern comforts and local character, with thoughtfully curated decor that reflects the vibrant spirit of our neighborhood. Relax in a cozy, stylishly furnished living space.

Top guest favorite

A spacious studio living area is presented with a queen size bed positioned next to a comfortable couch. A wooden dining table with chairs is visible, accompanied by a kitchenette featuring modern cabinetry and appliances. Natural light enters through a unique angled window.

Guesthouse in Chardon

4.95 out of 5 average rating, 264 reviews

Chardon Loft

Large private 2nd floor studio style living area with queen size bed, couch, table/chairs, TV, refrigerator, microwave, hot plate, NO OVEN OR STOVE TOP, sink, large shower, A/C, heat, washer and dryer, and deck. Wifi internet is provided. The television has Netflix. No cable channels. The furnace is nontraditional. It is not located in a closet. The noise when running and starting will be louder than normal during winter months. Ear plugs are available for those that are noise sensitive.

Top guest favorite

A light-filled living area features a blend of modern and cozy elements, including a seating arrangement with a brown futon and two accent chairs. A glass coffee table is centered on a decorative area rug, while natural light filters through the window, enhancing the serene ambiance.

Apartment in Shaker Heights

5 out of 5 average rating, 44 reviews

Charming 2Br Near Van Aken/Hospital/CWRU (2nd FL)

This newly renovated 2BR 1Bath home is located in a safe, peaceful and friendly neighborhood in the heart of Shaker Heights. Our home offers great convenience and is surrounded by the area's best shopping and dinning - walking distance to Heinen's and CVS; 5 minutes to Van Aken District; 10 minutes to Beachwood and Pinecrest; 15 minutes to Cleveland Clinic, UH, University Circle, Orchestra, Art Musem; and close to major employers. It is situated near public transportation, I-271 and I-480.

Top guest favorite

An entertainment lounge is featured with a space-themed mural depicting an outer space view. Red accent lighting highlights the modern seating area, which includes a red couch and light-colored coffee tables. A large TV is mounted on the wall, enhancing the inviting atmosphere.

Home in Warrensville Heights

4.97 out of 5 average rating, 121 reviews

NEW! Stylish Galactic Getaway

Enjoy your stay at a newly updated Lux Airbnb! Surrounding Locations: - Cleveland Clinic | 20 mn - Pinecrest | 6 mn - Beachwood Place | 10 mn - Legacy Village | 10 mn - Hopkins Airport | 20 mn Housekeeping/Guidelines: - Before check-in, the unit will be thoroughly cleaned and inspected. - We ask you to treat our Airbnb with respect as if it was your own. - Damaged/Stolen items = Additional Fees. - The home's security code will be issued upon the reservation date. - No Smoking!

Top guest favorite

A bright living area features a spacious sofa adorned with patterned cushions, complemented by an area rug with intricate designs. Large windows allow natural light to fill the space, while a decorative table and various accent lamps add warmth and charm. French doors provide access to the outdoor patio.

Home in Cleveland Heights

4.94 out of 5 average rating, 181 reviews

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.