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.

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.

NEW Beautiful 1920 house walkable 8 GUEST

Welcome to our charming 1920 home in the heart of Harrisonville, Missouri! This 4-bedroom, 2.5-baths home blends historic charm with modern comforts, offering a cozy retreat for couples, families, or friends. We are pet-friendly, so feel free to bring your furry companions along! Just a 2 min walk to the historic Harrisonville square with restaurants, coffee shops, bakery, wine bar and boutiques. This home offers easy access to the best of Harrisonville and the surrounding Kansas City area.

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*

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.

Nick's Place

*This is a smoke-FREE property* Need a home away from home? Come stay in our beautiful, fully renovated A-frame home on 3 secluded acres. Whether you are coming to visit the KC area or looking to get away from the city, we have you covered. Located just off 150 Hwy with quick easy access to I-49 Hwy, and 291 Hwy we are 30 minutes from the Country Club Plaza, Kauffman and Arrowhead Stadiums, and Downtown Kansas City. 50 minutes from Kansas City International Airport.

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.

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