Holiday rentals in Pleasant Hill

Coveted Museum District Stylish Eastlake Victorian

Step into this exquisitely renovated Eastlake Victorian on tranquil Oak St, in Kansas City’s vibrant Southmoreland, steps from Nelson-Atkins, KCAI, Plaza, and Westport. This 3-bed, 2-bath gem boasts soaring ceilings, floating cedar shelves, and a private backyard patio for serene retreats. Enjoy designated parking and a walkable Museum District, just 4 blocks from the Main Street. Blending historic elegance with modern flair, this chic haven promises an unforgettable stay in KC’s cultural heart.

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!

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.

Charming Mid-century Home DTLS - FIFA World Cup

In downtown Lees Summit, our 2-bed, 1-bath Airbnb blends modern design with historic charm. Luxurious king-size bed in the master, a twin trundle bed in the guest room with dedicated workspace. Stylish bathroom with modern fixtures. Perfectly located for dining, shopping, and entertainment. Cozy living space, well-equipped kitchen. Fast WiFi. Your ideal home away from home in vibrant downtown. Just a short drive to Arrowhead / GEHA Field! Book now for an unforgettable Lee’s Summit adventure!

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*

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.

Studio Guest House

Enjoy Southern OP in this quiet neighborhood. Our studio guesthouse has a full kitchen, TV, a new a/c/heater, and google fiber internet. In case you get lonely, we have 2 friendly dogs always looking for attention. We are about 45 minutes away from the Kansas City airport, Kauffman Stadium, Arrowhead Stadium, the KU main campus, and the Harry S Truman sports complex. We are 10-15 minutes from the Scheels soccer complex. Overland Park has plenty of Kansas barbecue and shopping.

Hummingbird Vista

Hummingbird Vista is located in tranquil Unity Village, just minutes from Kansas City and Lee’s Summit (and 20 minutes from the Truman Sports Complex). The 3-story, English Cotswold-style home on the 2nd hole of the Unity Village golf course has 4 bedrooms, 2 baths, and can comfortably sleep 12 people. It features a wet bar and fireplace with remote control. Perfect for large families, reunions, retreats, etc. Includes access to a state-of-the-art fitness center.

Skyline | Hot tub | Rooftop Patio | Amazing Views

Hot tub, fire pit, rooftop patio and amazing views of the KC Skyline! Brand new home, with comfortable king size beds, 3 tv's and modern decor. Outdoor grill, picnic table, wood fire pit and rooftop gas fire pit. Hammocks, corn hole and board games. After booking, guests are required to complete a renter’s agreement and provide a valid government-issued photo ID prior to check-in. This is required for all guests without exception.

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.

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