Holiday rentals in Pleasant Hill

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Top-rated holiday rentals in Pleasant Hill

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Top guest favourite
A spacious living area features original hardwood flooring and exposed brick walls. Comfortable seating options include a leather sofa and armchair. Large windows allow natural light to fill the room while potted plants add a touch of greenery to the inviting space.
Loft in Leavenworth
4.97 out of 5 average rating, 398 reviews

Follow Lincoln's Steps at Queenie's Loft in Leavenworth

Look out at the pristine City Hall with the Statue of Liberty and a bronze sculpture marking the city where Honest Abe visited just before announcing his run for Presidency. The original bricks and hardwood in this unique 170-year-old home have stood the test of time. Take a an elevator (or stairs) to the 2nd floor. Located in the heart of historic downtown Leavenworth, the First City of Kansas. Within a few blocks are several coffee shops, bakeries, boutiques, and bars. Located only 10 miles from the award-winning tourist town of Weston, which has many breweries, wineries, and hiking trails. You won't find this anywhere else! Original wide hardwood floors that were laid 165 years ago and the original brick walls that have stood the test of time. A view from nine windows that overlook our pristine city hall with the statue of liberty and statue of Abraham Lincoln. (Lincoln announced his run for presidency right there in Leavenworth!) And to think, he most likely walked across the street and came in our building as it was a saloon at the time! You will enter our loft from the street by keypad and there is a small room leading to our new elevator (big steel door) to take you to the 2nd floor. Directions for the elevator are on the wall. Very easy, just always close the white accordian door to elevator in case your party calls it from another floor. Your party is the only people who have access to this elevator. Check in is between 4 and 7pm. Please drop us a text if it is not in that time frame. Check out is 11am. Again, please drop us a text if you need more time! Mac and Stacy are always just a text away and can be there within 10 minutes. #913-651-7798. Text us with any questions! Ride a custom elevator to the open yet cozy space above the host's candle and gift boutique. The flat is a great base to explore KC, Fort Leavenworth, the county seat, and quaint Weston, MO. Shops, restaurants, coffeehouses, and bars are steps away. There is a large parking lot behind the building on 5th street. 65" tv, but we do not have cable. There is a dvd player, and you are welcome to hook your phone to the tv to watch your prime video, hulu, etc. That is what we do, and use the data from our phone or computer to display on the tv screen!

Top guest favourite
An aerial view captures the log cabin nestled on a green landscape. Surrounding trees frame a winding creek and lake in the background. The cabin features a circular stone patio area, with seating arranged around a central fire pit, enhancing the natural setting.
Home in Pleasant Hill
4.98 out of 5 average rating, 51 reviews

The Cabin at Big Creek

Ultimate Seclusion Nestled away on 120 acres this fully updated log cabin sets on a 5 acre private lake with a rolling creek. Approximately 20 miles from Arrowhead (GEHA Field) where the World Cup will be held. We get several inquires about small weddings, events, parties, etc. Owner has strict no more than 10 guests spending the night. However for micro weddings and events- as long as it stays under 50 people- the flat rate is 1950 plus fees. Can send special quote if wanting to book event

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!

Superhost
The entrance features a white railing leading up to a covered porch. A solid door, flanked by a window on one side, is highlighted by a wall-mounted light fixture. The exterior is painted a darker shade, contrasting with the white trim.
Townhouse in Pleasant Hill
4.88 out of 5 average rating, 104 reviews

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.

Guest favourite
A cozy living room is highlighted by a gas fireplace, framed by a faux brick surround. Comfortable seating includes a circular coffee table and two armchairs, with soft curtains on the window allowing natural light. Decorative elements add a welcoming touch to the space.
Home in Harrisonville
4.99 out of 5 average rating, 143 reviews

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.

Guest favourite
Barn in Greenwood
4.92 out of 5 average rating, 239 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
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, 143 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.

Guest favourite
Flat in Pleasant Hill
5 out of 5 average rating, 5 reviews

The Cozy Cove on the Rock Island Trail

Welcome to The Cozy Cove on the Rock Island Trail! Located just south of Pleasant Hill, MO, and 1.5 miles from the trail, our guest suite is a peaceful countryside retreat. Enjoy a kitchenette, laundry, and shared outdoor perks like a fire pit and pine grove. We’re only 40 minutes from Arrowhead Stadium—ideal for World Cup fans! Note: For multi-night stays, we may need occasional laundry access and will coordinate a time with you.

Superhost
Home in Pleasant Hill
5 out of 5 average rating, 3 reviews

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.

Top guest favourite
A comfortable living area features two blue sofas and a round coffee table atop a colorful rug. A wall-mounted television is positioned above a gas fireplace. Large windows provide views of the fenced backyard and natural light fills the space.
Cottage in Pleasant Hill
4.95 out of 5 average rating, 133 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.

Guest favourite
Flat in Pleasant Hill
5 out of 5 average rating, 41 reviews

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

Guest favourite
A charming two-story farmhouse is situated on a spacious corner lot, surrounded by well-maintained grass and mature trees. A welcoming red door provides entry, while a covered porch offers a shaded space with seating. The tranquil outdoor setting enhances the relaxation of the home's surroundings.
Home in Pleasant Hill
4.98 out of 5 average rating, 63 reviews

Newly Renovated Farmhouse ~ 35 min to KC World Cup

Our retreat is perfect for families visiting the area or bikers exploring the Katy Trail. Its prime location within walking distance of the charming Historic Downtown ensures convenient access to local attractions, biking and amenities. Bikers will appreciate the convenience of 4 indoor bike racks, providing secure storage for their equipment.

Popular amenities for Pleasant Hill holiday rentals

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