Vacation rentals in Pleasant Hill

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Top-rated vacation rentals in Pleasant Hill

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite
A bright living area features a dark sofa paired with a mid-century modern coffee table. Shelves are filled with decor and plants, while a plant stands nearby. Natural light enters through two windows with white blinds, illuminating the hardwood floor.
Guesthouse in Lee's Summit
4.9 out of 5 average rating, 626 reviews

The Cottage

The Cottage, with a studio style layout, is a bright and clean space just one mile from historic downtown lees summit with local shops, bars and restaurants. The cottage is ~20 min from downtown Kansas City and 15 min from Kaufman and Arrowhead Stadium. This newly renovated 1900s milk barn is unique and special with a lot of charm, with a few of the modern conveniences. Guests are welcome to take advantage of the two acre landscaped yard and enjoy a delicious s’more at the outdoor fire pit!

Top guest favourite
A cozy living area features a brown leather couch paired with a stylish side table and an eclectic floor lamp. A compact dining table with metal chairs is positioned near a large mirror, while natural light filters through the windows, enhancing the inviting space.
Home in Lee's Summit
4.92 out of 5 average rating, 135 reviews

Charming Mid-century Home DTLS

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!

Top guest favourite
A cozy sleeping area features a spacious bed with striped bedding and layers of soft blankets. A dark upholstered bench with textured throws sits at the foot of the bed. A bedside lamp provides soft lighting, and a decorative cabinet stands nearby.
Guest suite in Olathe
4.98 out of 5 average rating, 476 reviews

Secret Garden Short Stay

1 King Bed. 1 Twin air mattress rollaway (plz req rollaway) Washer/Dryer for your use. Wi-Fi Fiber. Sep. fenced backyard area with Priv. entry into your basemnt area that is located around the back of our main house. Parking space on prop. Dog park, walking trails. Pet fee is charged. Close to highwy, & shopping. We also have Solar panels that provide some back up for the heat/air and refrig. Entire daylight basement is separate from us upstairs with locked door. Does have couple of steps.

Top guest favourite
A broad driveway leads to a spacious building featuring a mix of brick and blue siding. Two garage doors are visible, framed by landscaped green areas and decorative fencing. The serene surroundings are complemented by trees in the background, creating a peaceful entrance.
Barn in Greenwood
4.91 out of 5 average rating, 195 reviews

Cozy private cottage/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*

Guest favourite
A charming exterior view of a historic home features a dark blue facade with white trim. A covered porch is visible, equipped with railings and a rocking chair. The yard is adorned with fallen leaves, and large windows allow natural light into the rooms.
Townhouse in Pleasant Hill
4.9 out of 5 average rating, 141 reviews

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.

Superhost
A cozy seating area features a brown couch and two light-colored armchairs facing a fireplace. A wooden coffee table and a small side table are placed between the chairs. Decorative shelves with plants and accessories are mounted above the fireplace.
Guest suite in Grandview
4.8 out of 5 average rating, 215 reviews

Cozy Guest Suite with Fireplace & Private Entrance

Come enjoy your stay at our home with a private entrance and outdoor patio in the back of the house in a quiet and peaceful neighborhood. You will have an entire guest suite to yourself including one bedroom with an attached bathroom as well as a pull out couch for additional sleeping arrangements. Prepare meals and cocktails at the wet bar before settling down in front of the fireplace and watching your favorite movie on the smart TV w/ access to free wifi.

Top guest favourite
A charming cottage features a welcoming front porch adorned with seasonal decorations. The exterior, painted in dark tones, is complemented by white pillars and large windows. Vibrant fall leaves blanket the yard, enhancing the natural setting. A gentle sun filters through the trees, creating a warm ambiance.
Cottage in Kansas City
4.98 out of 5 average rating, 643 reviews

Cheerful 2-bedroom cottage

Cheerful 2-bedroom cottage four miles from stadiums with free parking on premises. Family friendly with country feeling close to the city. Bathroom has a walk in shower. Large fully stocked kitchen with separate dinning area. Refrigerator with ice and water through the door. The kitchen has a dishwasher and a washer and dryer laundry area. Plus an added bonus a fully stocked coffee bar. Also added is a EV 240 volt receptacle for charging EV over night.

Top guest favourite
A cozy living area features a patterned couch alongside a light wood coffee table. Two lamps provide soft lighting, illuminating the hardwood floors. A chair and a folding chair offer additional seating, while wall art adds color and interest. Windows allow natural light to fill the space.
Guest suite in Lee's Summit
4.97 out of 5 average rating, 110 reviews

Vintage Space! Downtown Lee’s Summit

Super retro style upstairs apartment! This is the top story apartment of a home built in 1898. It is just a 5 minute walk to downtown Lee's Summit! It is close to restaurants, coffee shops, family-friendly activities, shopping, bars and a whole slew of entertainment. You’ll love the space because of the location, the ambiance, and the people. It is good for couples, solo adventurers, business travelers, and families (with kids).

Guest favourite
A bright living area features a modern couch adorned with colorful cushions. A small chair and table occupy one corner, and large windows provide natural light, offering views outside. A patterned area rug adds warmth to the space, enhancing the minimalist decor.
Home in Kansas City
4.95 out of 5 average rating, 988 reviews

Minimalist Modern Strawberry Hill Get-Away Home

Entire, separate entry, second floor studio. Minimalist modern decor, nice clean small space with everything you need. We aim to have your stay be an enjoyable experience, greeting you with a clean home, ensuring you have what you need during the stay, and being available as needed. Approximately 5-10 from downtown KCMO, Power and Light, City Market. Within walking distance of a few local family owned restaurants and bars.

Superhost
A charming cottage features a distinctive tower and is painted in light blue with dark blue trim. The entrance, adorned with a seasonal wreath, is flanked by a small seating area. A stone pathway leads to the steps, providing access to the welcoming porch.
Guesthouse in Lone Jack
4.91 out of 5 average rating, 332 reviews

Adorable cottage on Beautiful property w/ hot tub

Take it easy at this unique and tranquil getaway. Enjoy your own private cottage with all your essentials; You also have access to the property's hot tub and 1 acre pond stocked with catfish, blue gill, and bass! The cottage has a 1 queen size bed and a mattress in the loft . Please note: we do live on this property and the cottage is next to our main house. We have friendly outdoor cats they do freely roam the property.

Guest favourite
The charming cottage features a welcoming front porch with decorative railings and a vibrant red gable accent. Lush green grass surrounds the pathway leading to the entrance, which is adorned with an elegant door and large windows covered with lace curtains.
Home in Harrisonville
4.93 out of 5 average rating, 164 reviews

Emmons House, 1 min walk to Square, pet-friendly

This writer's retreat cottage is close to everything. It's a one- minute walk to historic Harrisonville Square where you find Brickhouse coffee, 1886 wine & food, Headquarters wine bar, District bar & food, Birdy's fun finds & clothing, Artisan's crafts & treats, chiropractors and medspa. Beck Event Space is just across the road. Within the house, unique treasures from around the world. Gorgeous deck space for relaxing.

Top guest favourite
A cozy living area features two navy blue sofas facing a circular wooden coffee table. Two light grey accent chairs are positioned nearby. A flat-screen television is mounted above a gas fireplace, with natural light coming through two windows. A colorful area rug enhances the space.
Cottage in Pleasant Hill
4.95 out of 5 average rating, 121 reviews

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.

Popular amenities for Pleasant Hill vacation rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Cass County
  5. Pleasant Hill