Holiday rentals in Pleasant Hill

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 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.

Fillmore Manor

Fillmore Manor is located in tranquil Unity Village, just minutes from Kansas City and Lee’s Summit (and 20 minutes from the Truman Sports Complex). A two-story, English Cotswold-style home on the 2nd hole of the Unity Village golf course, it has 4 bedrooms, 2 baths, and can comfortably sleep up to 10 people. It’s perfect for large families, reunions, retreats, and other special occasions. Your stay includes access to our state-of-the-art fitness center.

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 apartment, private entrance, gas fireplace

Walkout basement apartment with private outside entrance, private queen bedroom, full kitchen, living room with gas fireplace, separate office room (single bed is in the office) , lots of comfortable seating and full private bath. Plenty of natural daylight with full size windows and glass door in the apartment. Please be sure to review our house rules. There are not many, but they are important to adhere to.

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