Holiday houses in Cleveland

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Top-rated holiday rentals in Cleveland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
An open-plan dining and living area features a long dining table with black chairs. Off to the side, a cozy seating arrangement includes a sectional sofa and a coffee table. Natural light floods through large windows, and warm wood paneling creates a comfortable ambiance.
Loft in Louisburg
4.97 out of 5 average rating, 72 reviews

Modern Loft w/ Brick Walls, Pool Table + Sleeps 12

You are going to LOVE the Lowman Loft - a beautifully refurbished historic building right in the center of Louisburg, Kansas. Only straight highway 40 miles from Kansas City. The loft is 3,000 sq ft. Open dining, living and kitchen areas and four private bedrooms. A perfect option for your friends, families, or workmates, the loft is located in a beautiful neighborhood surrounded by antique shops, local wineries, and wedding venues that you can explore. A short drive to Overland Park or Olathe.

Guest favourite
A small wooden cabin is positioned on a grassy area, surrounded by trees. A wooden deck with chairs offers outdoor seating. Two hammocks are seen nearby, with a fire pit in the foreground. Soft evening light casts a gentle glow over the exterior.
Tiny home in Cleveland
4.95 out of 5 average rating, 97 reviews

Lux tiny off-grid cabin getaway

This getaway is the best off-grid camping experience you'll ever have. Said to be located on the ancestral farm of some of the world's most notorious outlaws (The Dalton Gang). This tiny secluded cabin is located on 10 acres of western Missouri prairie. With everything you need for a great night away from it all. But with all the modern amenities that an off-grid camping experience can offer, you don't have to live like a savage to experience what it was like to be a prospector in days gone by.

Guest favourite
The cabin exterior features a wooden facade with a covered porch and decorative beams. Surrounding greenery enhances the secluded setting. A flagstone patio is visible, alongside a gravel path leading to an outdoor BBQ area, creating an inviting outdoor space.
Cabin in Peculiar
4.93 out of 5 average rating, 28 reviews

New Cabin for an Adventure!

Beautiful Western Cabin that is well appointed for a once in a lifetime memorable night or two. The Cabin is secluded and nestled at the base of a ridge line with views of wildlife in the field. Flagstone patio, Table, BBQ, and open firepit provide an ambience with the outdoors to gaze at the stars. For bedding down, step inside the Cabin to a Living room,Queen bed and loft above with two beds, bathroom and shower,TV, StarLink,Full kitchen,LG Washer/Dryer,Coffee maker, and a designer decor.

Guest favourite
The guest house exterior is framed by lush trees, featuring a light brown siding with a shingled roof. Large windows allow for natural light, while a welcoming front porch enhances accessibility. A two-car garage is situated to the right of the entrance.
Home in Peculiar
4.91 out of 5 average rating, 226 reviews

Charming Getaway just south of Kansas City

*This is a smoke-FREE property* Do you have fond memories of staying at grandma's house as a kid? Then you'll love our spacious 1200 sq foot guest house on our beautifully treed, secluded 3 acre property, complete with hobby farm animals. Whether you are coming to visit the KC Metro area or looking to get away from the city, we have you covered. Located just off of I-49 highway, we are less than 30 minutes from the Country Club Plaza, Kauffman and Arrowhead Stadiums, and Downtown Kansas City.

Top Guest favourite
Guesthouse in Louisburg
4.96 out of 5 average rating, 150 reviews

Spacious Country Apartment with Modern Amenities

Welcome to Louisburg! Spacious, private entry, 1000 sq. ft. apartment above detached garage within minutes of wineries, antiques & Cider Mill. Set on 15 acres, and 2 miles down a gravel road, you are out of the city and seeing stars, with an amazing 2nd story view. Sleeps up to 6 with separate bedroom with queen bed and low ceiling (62” great for kids!) loft with 2 twins & a double. All wrapped in unique finishes including an amazing shower! Located only 45 minutes from downtown Kansas City!

Top Guest favourite
Barn in Greenwood
4.92 out of 5 average rating, 248 reviews

Cozy Private Barndominium/studio

Private studio on the second level of our detached garage behind our main house. Located in a resort-like property. Quiet and safe neighborhood. Minutes from downtown Lee's Summit. Coffee shop/bakery within walking distance. Several restaurants close by, 1 mile to iconic antique malls. Perfect place for traveling professionals. Close to Hwy 291. We use the garage for storage and to work on our vehicles occasionally, you might hear us working. *There is no smoking/vaping in the apartment*

Top Guest favourite
A well-appointed kitchen features full-size white appliances, including a refrigerator and dishwasher. Natural light enters through a skylight, illuminating the countertop and cabinetry. Decorative accents and a floral arrangement enhance the space, creating a functional and inviting atmosphere.
Barn in Bucyrus
5 out of 5 average rating, 32 reviews

Dairy Barn Loft Apartment

Enjoy the sounds of nature when you stay in this unique place. Former dairy barn hayloft converted into adorable loft apartment. Enjoy extreme peace and quiet. 20 minutes south of shopping and some of the finest restaurants the Kansas City area has to offer. This dairy Barn offers Wi-Fi, full size appliances, washer and dryer, two flat screen televisions with Roku. King size bed and queen size hideaway bed couch. Please contact the host for a link to the video of this hidden gem.

Top Guest favourite
A welcoming two-story home is surrounded by a manicured lawn, featuring vibrant flower beds. Rocking chairs are positioned on a large front porch with hanging planters. The sun casts gentle shadows across the neatly trimmed grass, enhancing the peaceful outdoor setting.
Home in Cleveland
4.97 out of 5 average rating, 121 reviews

Meadow Brooke Lane

Nested on 3 beautiful acres of fenced land. 4 bedrooms (3 with ensuite), fully equipped kitchen, projector, fire, bbq, plus more! This property is located near multiple event spaces making it ideal for small gatherings or enjoying the countryside. Kids and pets alike with love the vast outdoor space to roam and play. There is a charming train that runs the backside of the property making for a unique and fun backdrop. A fantastic dog friendly brewery is within walking distance.

Top Guest favourite
The exterior of a charming studio guesthouse is presented, featuring a white façade with decorative white trim. Two large windows and a door with a small wreath add to the inviting look. A black vehicle is parked in front, surrounded by greenery.
Guesthouse in Shawnee Mission
4.99 out of 5 average rating, 250 reviews

Studio Guest House

Enjoy Southern OP in this quiet neighborhood. Our studio guesthouse, completely separated from the main house, has a full kitchen, TV, a new a/c/heater, and google fiber internet. In case you get lonely, we have 2 friendly dogs always looking for attention. We are about 45 minutes away from the Kansas City airport, Kauffman Stadium, Arrowhead Stadium, the KU main campus. We are 10-15 minutes from the Scheels soccer complex. Overland Park has plenty of Kansas bbq and shopping.

Guest favourite
A spacious reproduction Conestoga wagon is positioned on a gravel surface, with a covered outdoor kitchen nearby. The vibrant sunset paints the sky in warm colors, while the surrounding grassy area offers an open, tranquil setting for relaxation.
Farm stay in LaCygne
4.96 out of 5 average rating, 113 reviews

Covered Wagon1 @IsinglassEstate

Isinglass Estate is anything but ordinary. Our reproduction Conestoga Wagons have it all- with heat, A/C, a full bathroom, your own private outdoor kitchen and firepit, and five star details to complement the 100acre views of the polo field and vineyards! Wagon guests enjoy access to our 600 acre estate with fishing, hiking, vineyards, blackberries, a petting zoo, horseback rides, horse-drawn carriage rides, plus a restaurant and winery tasting room all on-site.

Top Guest favourite
A tree-lined lane showcases tall, bare trees flanking a gravel driveway leading to a red barn. The scene is set against a backdrop of soft, warm light filtering through the branches, hinting at a peaceful countryside atmosphere.
Guesthouse in Cleveland
5 out of 5 average rating, 70 reviews

Guest Suite Retreat: A Southern KC Gem

Relax at our peaceful guest house in Cleveland, set in the countryside near several popular country wedding venues. It’s perfect for up to 4 guests, with a king-size bed, twin daybed, and pullout twin. Whether for a wedding or a relaxing getaway, you'll love the charm of this cozy retreat. Within 15-25 minutes from Louisburg, Belton,Overland Park and just 30 minutes from GEHA Field at Arrowhead, it’s the perfect mix of country comfort and modern convenience.

Top Guest favourite
Townhouse in Olathe
4.97 out of 5 average rating, 172 reviews

Chic Family Home with Fenced Yard

Welcome FIFA - can accommodate groups. Two AirBNBs side-by-side. Completely renovated and stylish, this home is perfect for families, groups. Enjoy walking trails and playgrounds just steps away. Sleeps 6 to 8 with 2 bedrooms, 1.5 baths, king and two full beds, plus finished basement. Conveniently located near Overland Park and Olathe sports complexes, making it ideal for baseball, softball, soccer tournaments.

Popular amenities for Cleveland holiday rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Cass County
  5. Cleveland