Holiday rentals with a pool in Middleburg Heights

the Black Barn Guest House

Totally renovated and finished in in 2025 This unique place has a style all its own. Restored 1899 barn on peaceful, resort like setting. This cozy barn guest house is perfect for a romantic get away, or those who want a cozy, comfortable retreat. We are surrounded by trees, yet neighboring homes are nearby. 25 minutes from Cleveland Hopkins airport. 30 minutes from Downtown Cleveland. 5 minutes to charming Valley City or Columbia Stations newest gem, Red Wagon Brewery and Farmers Market.

Stillwater Retreat-Waterfall·Pond Horses·Firepit

Experience refined living at this elegantly appointed country estate, tucked into a secluded and pristine valley. Surrounded by natural beauty, the property features wooded walking trails that follow the west branch of the Cuyahoga River and offer sweeping views at every turn. Enjoy peaceful mornings overlooking the pond, afternoons exploring shaded forest paths, and golden evenings framed by autumn foliage and stately pines. Blending rustic charm with elevated comfort and private relaxation.

Boho Star Pad on Madison-beautiful & cozy 1 bd rm

Brand new one bedroom with all the comforts of home. Your own private apartment is centrally located in Lakewood above the local favorite Taco Tontos known for amazing craft cocktails, baked burritos & jumbo tacos! Walking distance to Madison park & municipal pool, restaurants, bars, shops & music venues. Five minutes to our beautiful lakeshore parks & a ten minute drive to downtown: Playhouse Square, Guardians, Cavaliers, Browns Stadium, Rock & Roll Hall of Fame & 15 minutes to CLE airport.

Your home away from home!

Welcome to your away from home! One bedroom MIL suite in private home with spa quality bathroom ( tiled walk-in rain shower, with body jets, heated towel bars, and heated heated floors). Gas fireplace. Fully equipped kitchen. Private front and back entrance. Seasonal (May - Oct) use of pool, deck, grill and shared backyard space. High speed internet, cable TV, Netflix, Hulu, HBO, etc..Driveway parking. No Pets. No Parties. No smoking. We are fully vaccinated. COVID cleaning protocols

Slow Burn | Urban Oasis Near Downtown CLE

Welcome to Slow Burn, one of four boutique suites located within Tremont's newest apartment community, Driftwood! Our modern, efficiently designed suites offer a perfect blend of comfort and style. Featuring floor-to-ceiling windows, each space is filled with natural light, creating an open and airy feel despite its cozy footprint. Carefully selected finishes, decor, and warm architectural lighting add to the inviting atmosphere, making it an ideal retreat for solo travelers or couples.

Luxury Apt w/ Rooftop Pool, Hot Tub & Skyline View

This stylish corner unit features an eclectic industrial design with exposed ductwork and a quiet, spacious layout. Enjoy a glimpse of Progressive Field from the living room and relax on your private balcony. The 725 sq ft space includes a fully equipped kitchen, smart TV, and generous closet space—perfect for extended stays or business travel. *The map shows a parking lot because this building was recently constructed on a former parking lot and opened just months ago!* FREE PARKING

Winter skiing, hot tub/Summer pool, national park.

Welcome to our property that sits on 6 gorgeous acres of land near Cuyahoga National Park and bursting with every amenity! The 7 bedrooms & 6000 sq ft of living space doesn't scratch the surface of what this place has to offer. Relax in the indoor hot tub complete with a bar located in the sunroom or take a dip in the resort sized heated outdoor pool with gazebo (pool open May-Sept) & finish the night in the 9 seat movie theater complete with surround sound or shuffleboard game room.

Central Flat: Heated Pool, Rooftop, Gym

You can stop your search now. You just found the perfect place to book for your trip to Cleveland. ➹ Clean. Robust Amenities. Modern Finishes. Quick Host Responses. ➹ You're going to be located at the CENTER of everything in Downtown Cleveland. ➹ Get a good night's sleep with our memory foam beds. ➹ Spend your daytime working from home at our private home office. Cook a meal for your group in our beautiful, timeless kitchen. Then spend your evenings relaxing with our 55" Smart TV.

Luxury Spa+Theater+Gameroom | CasaMora

From the co-founder of Joshua Tree Hata Retreat comes Cleveland's first fully immersive luxury experience. Whether going back and forth between the sauna and plunge pool, sipping wine by the 120-year-old upcycled sandstone fireplace, competing in ping pong and shuffleboard, or lounging on the oversized couch watching a movie while picking your favorite treats from the candy station, this centrally located home (just 5 minutes from any stadium) won't allow you to become bored.

Heated Pool + Saltwater Hot Tub | Family 3BR

Heated Pool + Saltwater Hot Tub Spacious 3BR West Park Oasis. Private backyard retreat perfect for families & quiet stays (no parties/events). 10 min to Cleveland Hopkins Airport (CLE) & Downtown, 45 min to Cedar Point. Features: Heated pool (Apr–Sept), year-round spa, & fenced yard. Fast Wi-Fi & dedicated workspace. Walkable to dining in a safe, quiet neighborhood. The perfect blend of relaxation and convenience for your Cleveland stay. Book your private getaway today!

Swim & Relax - Pool, Hot Tub and Renovated

Welcome to your dream retreat in our charming, split-level home in Parma! - Enjoy a private outdoor pool with sun loungers and pool toys. - Relax by the fire pit or BBQ on the private patio. - Newly remodeled kitchen equipped with modern appliances and quartz countertops. - Stay entertained with a 48" HDTV, Netflix, arcade games, and a game console. - Fast Wi-Fi and a dedicated workspace perfect for remote work. - Secure and private with a fully fenced backyard.

Luxe Lil' Italy 2BR | Sleeps 6 | Free Parking+Gym

Live in the heart of Little Italy, steps from University Circle, UH, and CWRU, with the Cleveland Clinic just minutes away. This professionally designed 2BR 1BA suite has: ✓ Sleeps up to 6 ✓ Includes secure gated parking ✓ A gym ✓ An in-unit washer/dryer ✓ and resort-style community amenities Whether you’re visiting for work, medical travel, or a city getaway, this centrally located space offers comfort, convenience, and a refined place to recharge.