Holiday rentals with a pool in Cleveland

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.

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

Chagrin Falls Private Suite

Private in law suite on 2 acre wooded setting in Bainbridge Twp., just minutes to historic Chagrin Falls and easy access to freeway to head downtown to explore downtown Cleveland. Suite has full kitchen, private bath with walk-in shower, 1 bedroom with queen bed and walk-in closet, covered parking, patio area with fire pit. Main home is occupied by hosts and suite has private entrance but shared laundry room (available for extended stays) that connects main home to suite with locking doors.

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

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 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 🌿

Central Flat w/ Pool & Sauna • Gym • Heart of DT

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 65" 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.

Stylish Chic Downtown Apartment

Stylish chic 1 level apartment located in the heart of downtown Cleveland. Short walk to Playhouse Square, Cleveland sports arenas, Tower City Center and JACK Casino. Short drive to Rock & Roll Hall of Fame, Cleveland Museum of Art, University Circle, Cleveland Clinic and Cleveland Metroparks Zoo. This 2 bedroom 2 bath apartment is fully equipped with all kitchen essentials, laundry and access to an incredible 24 hour facility which includes pool, indoor track and gym.

Ultimate Group Escape | Heated Pool 12 Guests

🏡 4 bedrooms • 7 beds • 2.5 bathrooms • Sleeps 12 🏊 Private in-ground pool • lounge chairs (open Memorial Day - Labor Day) 🕹️ Arcade games • cozy sunroom w/ string lights 🍳 Stocked kitchen • dining for 10 + breakfast nook 🔥 Fire pit for family fun 🐕 Pet friendly w/fully fenced in backyard 📺 Smart TVs • family-friendly layout 📍 Quiet neighborhood, near dining, shops, & parks The ultimate group getaway! Perfect for families, reunions, or weekends with friends!

Downtown Cleveland Luxe Stay | Walk to Stadiums

Modern 1BR Downtown Cleveland apartment with a king bed, steps from stadiums, restaurants, bars, and nightlife. Enjoy fast Wi-Fi, smart TV, full kitchen, free parking, and self check-in. Perfect for business travelers, couples, or extended stays, with stylish comfort and easy access to the waterfront, entertainment, and top attractions. Experience a seamless, memorable Cleveland stay in a prime, convenient location. June 2026 discounts applied.

Modern Univ Circle Suite | UH/CWRU | Gated Parking

Stay in the heart of Little Italy, steps from University Circle, University Hospital, and Case Western Reserve University, with the Cleveland Clinic just minutes away. This modern 1BR suite: ✔️ Sleeps up to 4 ✔️ Includes secure gated parking ✔️ In-unit laundry ✔️ Gym in Building ✔️ High-speed WiFi ✔️ Access to resort-style amenities All are ideal for medical professionals, business trips, couples, small families, and extended stays.