Holiday rentals in Pleasant Hill

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.

3BR/1BA Ranch Home | 45 min to KC | World Cup

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.

KC Stadium/FIFA - Chef kitchen-King bed - 4 TVs

🏟️ Prime Location – 8 min to Arrowhead & Kauffman Stadium. Centrally located and just minutes from major highways, this home is about 17 minutes from downtown Kansas City You’ll also find plenty of restaurants and shopping nearby. We take pride in offering a clean, comfortable stay for all our guests. The home features a custom kitchen with a 48-inch stove, double ovens, and a griddle. Enjoy a fenced yard with a propane grill for daytime BBQs, then unwind in the evening around the fire pit

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*

Meadow Brooke Lane

Nested on 3 beautiful acres of fenced land. 4 bedrooms (3 with ensuite), fully equipped kitchen, projector, fire, bbq, plus more! This property is located near multiple event spaces making it ideal for small gatherings or enjoying the countryside. Kids and pets alike with love the vast outdoor space to roam and play. There is a charming train that runs the backside of the property making for a unique and fun backdrop. A fantastic dog friendly brewery is within walking distance.

WoodsideView/ Private Suite

Relax in this quiet peaceful retreat. Spacious suite with one bedroom and second bed tucked away in adjacent room. Large bathroom with jacuzzi tub and shower. Kitchenette with microwave, toaster, coffee maker and full size refrigerator. No stove/oven. Private entrance and on-sight parking. Quiet suburban neighborhood close to lakes and trails. Hosts live upstairs and are available to help make your stay a memorable one. No smoking, no unregistered guest. Quiet hrs 10pm - 7am

Covered Wagon1 @IsinglassEstate

Isinglass Estate is anything but ordinary. Our reproduction Conestoga Wagons have it all- with heat, A/C, a full bathroom, your own private outdoor kitchen and firepit, and five star details to complement the 100acre views of the polo field and vineyards! Wagon guests enjoy access to our 600 acre estate with fishing, hiking, vineyards, blackberries, a petting zoo, horseback rides, horse-drawn carriage rides, plus a restaurant and winery tasting room all on-site.

The Waldo Walkabout - Pet Friendly + Fenced Yard

🏡 Waldo Walkabout – Your cozy KC bungalow! 🛏 2 Queen bedrooms with Smart TVs 🛁 1 spa-like bathroom with luxury Tommy Bahama products 🍳 Fully stocked kitchen + coffee bar (Keurig, French press, pour-over) 🛋️ Living room with plush sectional & 55" Smart TV 🍽️ Dining table for 6 + mixology set 🌳 Fully fenced backyard & shaded deck 🐾 Pet-friendly with secure yard 🚗 Private driveway & street parking in vibrant Waldo neighborhood

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.

Adorable cottage on Beautiful property w/ hot tub

Take it easy at this unique and tranquil getaway. Enjoy your own private cottage with all the essentials for a comfortable stay. The cozy space is just under 200 sq ft and features a queen-size bed plus a loft mattress. Guests may enjoy exclusive access to the hot tub (lower level of main house) and a 1-acre pond stocked with catfish, and bluegill.

Rock Valley Ranch Cottage on 15 acres, sleeps 4

Enjoy a peaceful stay at our newly remodeled cottage near Lone Jack. A beautiful property on 15 acres, overlooking a pond, roaming horses and an array of wildlife. Located just 15 minutes east of Lee's Summit and 35 minutes from the Plaza. Join us for a weekend away or stay all week with friends and family at Rock Valley Ranch!

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.