Holiday rentals in Pleasant Hill

Soaking Pool • Hot Tub • 27 min to Arrowhead

Escape to KCcabin — a modern, secluded retreat in the Lake Lotawana area (no lake access). This new-build hideaway offers 2 bedrooms plus bunk beds, NEWLY ADDED soaking pool and hot tub with wooded views, spacious deck & grill, 65" smart TV, WiFi, washer/dryer, and a workspace with standing desk. Just minutes to dining, marinas, and only 30 min to downtown KC. Perfect for families, couples, or remote work getaways. If you'd like to view a walkthrough video, message me and I can send you a link.

Cozy home, World Cup- walk to FIFA Fan Shuttle

The Harris House is a real gem nestled in the heart of Historic DT Lee’s Summit! Just steps away, enjoy shopping, restaurants/bars, coffee shops, Farmer’s Market, & much more! Across the street is Harris Park & Summit Waves water park! Catch a train ride on the Amtrak, or just enjoy the nostalgic sound of the trains as they travel thru this quaint little town! Perfect space for out of town work! Easy hi-way access to Chiefs & Royals stadiums, DT KC, The Plaza, about 20 min from everything KC!

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.

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*

The Perch at The Roost

Welcome to The Perch at The Roost! Perched above historic downtown Pleasant Hill, this beautifully restored 100+ year-old Craftsman Victorian blends timeless charm with modern comfort. The Perch is a private upper-level unit featuring 2 bedrooms and 1 bathroom, offering a cozy and thoughtfully updated space to relax. Step outside and enjoy walkable access to local shops and community events in the heart of town. There is a staircase to reach this unit that is on the interior of the home.

Exquisite Family Haven On 11 Acres

Set in a serene and picturesque location, this exquisite home offers the perfect balance of luxury and comfort with a country feel. With space for up to 11 guests, this home is an ideal retreat for families and small goups. The gourmet kitchen is fully equipped for any culinary endeavor, with a huge island for family gatherings. The outdoors is where this property truly shines. This finely manicured 11 acres provides walking trails, 3 patios and privacy for a peaceful retreat.

Drew's Den in Historic Downtown Pleasant Hill, MO

Stay in private unit in Historic Downtown Pleasant Hill! Suite is located right on the Rock Island/Katy Trail! Beautiful 1920's home renovated into 3 private suites. This suite features a private bedroom with king memory foam bed, bath and full kitchen. Watch a movie in the spacious living area or curl up with a book in the bay window. In suite laundry provided for your convenience. Kitchen provides fridge, stove, microwave, coffee maker, toaster and basic cooking utensils.

The Cabin at Big Creek

Ultimate Seclusion Nestled away on 120 acres this fully updated log cabin sets on a 5 acre private lake loaded with fish with a rolling creek. Approximately 20 miles from Kansas City. We get several inquires about small weddings, events, parties, etc. Owner has strict no more than 10 guests spending the night. However for micro weddings and events- as long as it stays under 50 people- the flat rate is 1950 plus fees. Can send special quote if wanting to book event

Nick's Place

*This is a smoke-FREE property* Need a home away from home? Come stay in our beautiful, fully renovated A-frame home on 3 secluded acres. Whether you are coming to visit the KC area or looking to get away from the city, we have you covered. Located just off 150 Hwy with quick easy access to I-49 Hwy, and 291 Hwy we are 30 minutes from the Country Club Plaza, Kauffman and Arrowhead Stadiums, and Downtown Kansas City. 50 minutes from Kansas City International Airport.

Rock Valley Ranch Farmhouse, 15 acres, sleeps 14

Enjoy a peaceful stay at our newly remodeled farm house in Lone Jack. A beautiful ranch set on 15 acres overlooking a pond and fenced roaming horses. Spend a weekend away to gather with friends and family, host a small group event, or business meeting! The home has five bedrooms, three full bathrooms. and an open kitchen designed for entertaining. For outdoor festivities, there are two large porches and a separate pavilion! Located 15 minutes east of Lee's Summit.

The Cozy Cove on the Rock Island Trail

Welcome to The Cozy Cove on the Rock Island Trail! Located just south of Pleasant Hill, MO, and 1.5 miles from the trail, our guest suite is a peaceful countryside retreat. Enjoy a kitchenette, laundry, and shared outdoor perks like a fire pit and pine grove. We’re only 40 minutes from Arrowhead Stadium—ideal for World Cup fans! Note: For multi-night stays, we may need occasional laundry access and will coordinate a time with you.

Cozy cottage, perfect for traveling families.

There is a cozy gas fireplace that always sets the right mood. The open kitchen is fully equipped for cooking & baking. The back yard is fenced-in, perfect for kids & pets. There is a pond and lovely nature trail just outside the back gate and a children's park across the street in the front of the house. Walkable to nearby grocery, wine/spirits, gym, & restaurants. Available for 27 day rentals or more.