Vacation 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.

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.

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*

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.

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.

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.

Creekside Farmhouse - Group Stay Near Kansas City

Welcome to our spacious 2-story farmhouse, perfect for groups visiting the Kansas City area. Located 30–40 minutes south with direct highway access, it’s an easy base for events and the 2026 FIFA World Cup. Enjoy an open floor plan, fully equipped kitchen, cozy gathering spaces, and a relaxing front porch. The home sits beside Stillmeadow, with our coffee shop Cultivate just across the street.

Cozy downtown cottage

This cute cottage is in the heart of historic downtown Lee's Summit, a short walk from great restaurants, coffee shops, bars, and entertainment. It has a fully functional kitchen, and living room, mature trees, 10-foot ceilings, and a relaxing vibe. You’ll love the neighborhood, the great kitchen, and the coziness, all while being situated within easy highway access to Kansas City.

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