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!

Lauren's Loft in Historic Downtown Pleasant Hill

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, a loft with 2 twin beds, bath and kitchenette. Relax in the comfy living room watching TV or reading. In suite laundry provided for your convenience. Kitchenette provides fridge, microwave, coffee maker(and supplies), toaster, dishes and basic cooking utensils.

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*

Secluded 21-Acre Retreat w/Trails & Creek

Escape to your own private countryside retreat on 21 acres at B&S Creekside Retreat. This peaceful 2-bedroom, 2-bath home offers the perfect mix of comfort, privacy & nature. Enjoy morning coffee while watching wildlife, explore scenic walking trails, or unwind under the stars in a hammock . Whether you're looking for a relaxing getaway or a place to reconnect with nature, this space delivers. Inside, you'll find a clean, comfortable home with everything you need for a stress-free stay.

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.

The Landing at The Roost

Welcome to The Landing at The Roost! Located in historic downtown Pleasant Hill, this beautifully restored 100+ year-old Craftsman Victorian blends timeless charm with modern comfort. The Landing is a private lower-level unit featuring 2 bedrooms and 1 bathroom, offering a comfortable and thoughtfully updated space to unwind. Step outside and enjoy walkable access to local shops, dining, and community events in the heart of town.

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.

Cedar Hollow Bungalow, Lee’s Summit MO

This beautiful cottage-style bungalow has two bedrooms with queen size beds and one bath. This home has been completely renovated and is located on its own 1 acre plot with private parking and is part of a larger 20 acre farm. Enjoy waking up to the sounds of the birds, seeing other wildlife and a wooded walking trail beside a rocky stream in your own private get-a-way.

Square Side Stay

Fully remodeled 2BR/1BA home with everything brand new! Enjoy premium beds, a 65” smart TV in the living room, and 55” TVs in both bedrooms. Relax on the reclining sectional or cook in the fully equipped kitchen. Large backyard with gas grill. Washer/dryer included. Walk to historic Harrisonville Square with great restaurants, bars, and shops nearby.

Pilot's Pad Studio on 75 Acres + Fishing Pond

✈️ 1 Bedroom + Living Space • 1 Bath • Sleeps 3 ✈️ Breathtaking countryside views ✈️ King Bed + Futon Couch ✈️ Smart TV & High-Speed Wi-Fi ✈️ Fully Equipped Kitchen + Coffee Bar ✈️ Bar Height Dining for 2 ✈️ Luxury Tommy Bahama Bath Products ✈️ Private Patio with Fire Pit ✈️ Stocked Fishing Pond & Private Runway ✈️ Mini Split HVAC ✈️ Private Parking

Newly Renovated Farmhouse ~ 35 min to KC World Cup

Our retreat is perfect for families visiting the area or bikers exploring the Katy Trail. Its prime location within walking distance of the charming Historic Downtown ensures convenient access to local attractions, biking and amenities. Bikers will appreciate the convenience of 4 indoor bike racks, providing secure storage for their equipment.