Holiday rentals in Pleasant Hill

The Cabin at Big Creek

Ultimate Seclusion Nestled away on 120 acres this fully updated log cabin sets on a 5 acre private lake with a rolling creek. Approximately 20 miles from Arrowhead (GEHA Field) where the World Cup will be held. 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

3BR/1BA Ranch Home | Quiet | 35 Min to Kansas City

Just 40 minutes south of Kansas City in Harrisonville, MO! Come enjoy an updated three bedroom home with a fully stocked kitchen, two queen bedrooms and two twin bunks. There is one bathroom with tub and shower. During the fall and winter months, cozy up in the warm living room with a gas fireplace and a good book. An inviting back yard is perfect for grilling out, playing games and enjoying the quietude of a peaceful mid-century neighborhood. Full size washer/dryer use in unfinished basement.

Serene Countryside Glamping

Step back in time with a nostalgic stay in “Bella,” an iconic 25-ft Airstream. Tucked away in a quiet, treed corner of our one-acre property, Bella perfectly blends vintage charm with modern décor. Start your mornings on the intimate patio to a serenade of birdsong, and spend your evenings stargazing—you might even spot our resident owl. Located near the Rock Island/Katy Trail and just 40 minutes from Arrowhead Stadium, we offer the perfect peaceful retreat for World Cup fans this summer.

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.

Rebecca's Retreat Historic Downtown Pleasant Hill

Stay in private unit in Historic Downtown Pleasant Hill, MO!!! 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 kitchenette. Watch a movie in the spacious living area or curl up with a book. In suite laundry provided for your convenience. Kitchenette provides fridge, microwave, coffee maker(and supplies), toaster, dishes and basic cooking utensils.

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 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.

The Summers Silo

The Summers Silo is truly a one-of-a-kind tiny home carefully crafted from a converted grain bin. This fully furnished 1-bed, 1-bath retreat features warm pine floors, a private balcony, and a grill for outdoor dining. Set on 13 peaceful acres with access to scenic trails, this cute and unique retreat is perfect for relaxing, unplugging, and enjoying nature under the stars.

Cozy New Build near Harrisonville Square

Unwind in this newly built 3-bed, 2-bath home away from home just 45 minutes from Kansas City. Designed and built by our family, this home blends modern comfort with a peaceful, welcoming feel. Enjoy two queen bedrooms, a versatile twin trundle that converts to a king, a fully stocked kitchen, cozy living space, and fast Wi-Fi—just minutes from downtown Harrisonville.

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.