Holiday rentals in Highland Hills

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Top-rated holiday rentals in Highland Hills

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Top guest favourite
A spacious living area is furnished with a gray sofa, yellow accent chairs, and a mid-century modern coffee table. A large television is mounted on a stylish console. Natural light enters through large windows, complementing the neutral color scheme and patterned area rug, enhancing the cozy ambiance.
Flat in Shaker Heights
4.94 out of 5 average rating, 160 reviews

Relaxing Gem near CLE Clinic & Van Aken District

Unwind in this newly renovated 2BR 1Bath mid-century modern oasis in a friendly & vibrant Shaker Heights, OH neighborhood. This 1st 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 Bedroom w/ Queen Beds ✔ Relaxing Living Area ✔ Fully Equipped Kitchen ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Parking See more below!

Top guest favourite
A loft-style bedroom features a spacious bed with light bedding, set against blue and white walls. Natural light enters through a window, and a small lamp illuminates a bedside table. A textured area rug adds comfort to the hardwood floor.
Home in Cleveland
4.98 out of 5 average rating, 593 reviews

Cozy + Bright Lakeshore Cottage

Relax in this sunny cottage steps away from the Lake Erie shore. Comfy living room opens to the dining room (or home office - you choose!) Kitchen is well stocked and ready for the chef. Main bedroom and full bath are loft-style on the second level. Additional smaller bedroom and half bath on the first floor. Washer/dryer in the basement. Private driveway. Friendly and authentic Cleveland neighborhood. Terrific natural sunlight will brighten your stay and make THIS your Cleveland *happy place!*

Top guest favourite
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.
Flat in Cleveland Heights
5 out of 5 average rating, 194 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 favourite
A vibrant living area features a blue couch adorned with yellow cushions and a red decorative pillow. Colorful wall decor made of greenery and flowers adds a cheerful touch above the couch. Natural light is filtered through red and white curtains at two windows, enhancing the inviting space.
Flat in Cleveland Heights
4.81 out of 5 average rating, 123 reviews

The Cozy Zen

Explore Cleveland from this historic brownstone located in the center of iconic Cedar/Fairmount / University Circle! Filled with light & modern decor, this apartment is in walking distance to UH & CC hospital; the best landmark, restaurant & shops. Less than two miles from University Circle & only seven miles from Downtown Cleveland. There is so much to see & do, all within walking distance from this home. Can’t wait to meet you in Cleveland Cedar Fairmount / University Circle! NO PETS ALLOWED.

Top guest favourite
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.
Flat in Chagrin Falls
4.97 out of 5 average rating, 616 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.

Top guest favourite
Home in Little Italy
4.93 out of 5 average rating, 320 reviews

Historic Little Italy Garden Apartment

Stylish garden apartment. This retreat blends modern comfort with the vibrant cultural charm of Historic Little Italy. Steps away from shops, restaurants, and lively bars. Wade Oval Park is a nearby cultual hub, home to The Art & Natural History Museums and Botanical Gardens. Easy access to Case Western Reserve, Cleveland Clinic and University Hospital. Walk to the beautiful Lakeview Cemetary or take transit downtown to 4th street. Perfect for short or long stays. Book for a memorable time.

Guest favourite
A spacious living room features a light-colored sofa paired with a textured area rug. A coffee table holds a small plant and a remote. Natural light filters through sheer curtains over a 50" Flatscreen TV, illuminating the inviting space.
Flat in Shaker Heights
4.91 out of 5 average rating, 205 reviews

Historic District 2BR on 2nd Floor near CLE Clinic

Get comfy in this 2BR 1Bath historic district charmer 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!

Guest favourite
The spacious loft features an open-concept kitchen with modern appliances and sleek cabinetry. Natural light floods the area through large windows, illuminating the subtle brick wall and inviting seating area. Exposed beams add character to the vaulted ceiling, enhancing the room's airy feel.
Flat in Tremont
4.97 out of 5 average rating, 257 reviews

Perfect Studio Apartment in Heart of Tremont.

Enjoy your stay at this modern and newly updated, energy-efficient, spacious loft in the heart of Tremont, just a minute’s walk from all the bars, restaurants, cafès, parks, and vintage stores. Enjoy vaulted ceilings, central AC, a private furnished patio, the convenience of an in suite washer and drier, and a Nespresso coffee machine that is a coffee lover’s dream. The unit includes off-street parking for a small to medium sized car. We are pet friendly on a case-by-case basis.

Top guest favourite
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, 197 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.

Top guest favourite
The exterior of the house is shown, featuring a two-story structure with a shingle facade. A welcoming red door is flanked by green shutters. A short set of stairs leads up to the entrance, surrounded by well-kept landscaping and colorful flower beds.
Home in Cleveland Heights
4.85 out of 5 average rating, 137 reviews

Cozy, deadend street. Close to everything!

*HOUSE IS ntentionally BASIC IN EVERY WAY - THIS IS FOR DOGS FIRST. Intentionally NOT LUXERIOUS. Basic in decor. Furnished with all basics- kitchenware, dishes, pots, pans, silverware. Towels, bedding, etc. Located in the middle of "The Heights", you are within a 1/2 mile to restaurants, bars, movie theatre. Great location for medical residence, as it's close enough to Cleveland Clinic and UH, but in a fun, affordable neighborhood. *NOTE: AC is portable units-not central

Top guest favourite
Home in Warrensville Heights
4.97 out of 5 average rating, 129 reviews

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

Guest favourite
A stone fire pit is surrounded by a circular arrangement of natural rocks, with logs integrated into the design. Bright green chairs offer seating nearby, while a gravel path leads to a log cabin nestled among tall trees in the background.
Cabin in Solon
4.87 out of 5 average rating, 188 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!!

Popular amenities for Highland Hills holiday rentals

  1. Airbnb
  2. United States
  3. Ohio
  4. Cuyahoga County
  5. Highland Hills