Holiday rentals in Pleasant Hill

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Top-rated holiday rentals in Pleasant Hill

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

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Top guest favourite
A dining area is highlighted by a round wooden table surrounded by four gray chairs. Floating shelves are adorned with books and decorative items. A large potted plant adds a touch of greenery, while a decorative mirror reflects light and space.
Home in Kansas City
4.99 out of 5 average rating, 135 reviews

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.

Top guest favourite
A single-story bungalow is surrounded by lush green grass and large shade trees. The light-colored exterior features a bold blue front door, and multiple windows showcase views of the well-maintained yard. A paved driveway leads to an adjoining garage.
Home in Lee's Summit
4.97 out of 5 average rating, 146 reviews

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!

Top guest favourite
The kitchen and dining area feature modern appliances and a spacious layout, with a white dining table surrounded by six chairs. Natural light enters through a large window, illuminating the room. A decorative floral centerpiece adds a touch of warmth to the table.
Home in Harrisonville
4.99 out of 5 average rating, 142 reviews

3BR/1BA Ranch Home | 45 min to KC | FIFA 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.

Guest favourite
Bungalow in Kansas City
4.96 out of 5 average rating, 440 reviews

Near Downtown | Sauna | Plunge Pool | Tiki Lounge

A 125-year-old bungalow packed with personality. Inside you’ll find curated worldly décor, many lounge spaces, and the house’s most famous feature: the Lucky Kitty Tiki Lounge, a hidden bar built inside the old garage. Outside, relax in the barrel sauna, cold plunge, and stock tank pool, gather around the fire pit, and unwind under the string lights after a night exploring Kansas City. It’s a one-of-a-kind stay just minutes from downtown, the stadiums, and some of the city’s best restaurants.

Top guest favourite
Home in Lee's Summit
4.92 out of 5 average rating, 158 reviews

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!

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
4.92 out of 5 average rating, 236 reviews

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*

Guest favourite
A spacious loft features vaulted ceilings supported by exposed wooden beams. Natural light fills the room through large windows, illuminating the light hardwood flooring. A large sectional sofa and a cozy bed are arranged for comfort, with a wall-mounted TV visible in the background.
Loft in Kansas City
4.96 out of 5 average rating, 270 reviews

Truman Loft

Truly one of a kind Historic property converted into a spacious, cozy loft in the heart of South KC. This 100-year-old space(5 min from HS Truman farm. He spoke on this stage on his first political campaign) has been completely rennovated with concrete countertops, beautifully vaulted ceilings, huge bathroom, built in workspace and even a fun kid's room. Let the natural light pour through the massive windows or close the curtains and dim the lights:) We hope you enjoy it as much as us!

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, 145 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.

Top guest favourite
The kitchen features white cabinetry with modern appliances, including a stainless-steel refrigerator and oven. A window allows natural light to enter, illuminating the countertop and backsplash. The space is organized with clear views of the sink, dishwasher, and microwave.
Home in Blue Springs
4.96 out of 5 average rating, 207 reviews

Cozy 2 Bedroom Townhouse

Newly remodeled in March of 2023. Two bedroom townhouse each with a queen bed with a half bath downstairs and full bathroom upstairs. 2-3 minutes from I-70, Walmart, Home Depot, Texas Roadhouse and many other restaurants, fast food, and shopping. Kauffman & Arrowhead Stadiums (13 miles 15 minutes) Cable Dahmer Arena (6 miles 10 minutes) T-Mobile Arena (20 miles 20 minutes) KC Zoo & Starlight Theatre (20 miles 23 minutes) Worlds of Fun (23 miles 25 minutes) NO PETS ALLOWED

Guest favourite
The English Cotswold-style home features a distinctive exterior with a textured cream facade, red accents, and multiple gabled roofs. Large windows provide natural light, and the inviting front porch is furnished with chairs, surrounded by a lush green landscape.
Home in Unity Village
4.95 out of 5 average rating, 142 reviews

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.

Top guest favourite
The studio features exposed brick walls and wood-paneled ceilings, creating a warm ambiance. Two sleek seating chairs are positioned in front of large double doors that provide natural light. A dining table is visible in the background, accompanied by a minimalist pendant light.
Guest suite in Downtown Kansas City
4.96 out of 5 average rating, 1,123 reviews

WestSide Brick Barn Studio

The Brick Barn Studio is a sweet and peaceful private space on the first floor of a late 19th century Carriage House. Guests enjoy private entry to their accommodation, mini kitchen, shower/bathroom, and laundry, king mattress on a unique built-in bench platform, and a convertible sofa for another guest or two. There is a privacy curtain provided for guests who would like a little separation between the bed and sleeper sofa.

Top guest favourite
The open kitchen features dark cabinetry, modern stainless steel appliances, and a tile backsplash. A large window allows natural light to illuminate the space, while a circular dining table is visible in the foreground, offering a cozy spot for meals.
Cottage in Pleasant Hill
4.95 out of 5 average rating, 131 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 holiday rentals

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