Holiday rentals in Pleasant Hill

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Top-rated holiday rentals in Pleasant Hill

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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, 102 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.

Top 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, 141 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, 425 reviews

Plunge Pool • Tiki Lounge • Sauna • Near Downtown

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
A rustic cabin with a wooden exterior is surrounded by lush greenery. Large windows allow natural light to brighten the interior. A spacious deck is visible in front, with outdoor seating and a grill, offering a welcoming space for relaxation near the lake.
Farm stay in Excelsior Springs
4.96 out of 5 average rating, 318 reviews

San Vincente Lake Cabin at SundanceKC

Our beautiful light filled cabin with wood-burning fireplace is perched above our spring-fed 15 acre private lake next to the common outdoor lounge area and sand beach. We have 200 acres of gorgeous property with limestone boulders and hiking trails throughout. The lake is great for swimming, kayaking, stand-up paddle boarding and offers excellent fishing. We are five minutes from downtown Excelsior Springs, Excelsior Springs golf course and 3EX municipal airport. Relax, rejuvenate and play.

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, 155 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!

Top guest favourite
Barn in Greenwood
4.92 out of 5 average rating, 229 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 living area features a large, light-colored sectional sofa positioned on a textured area rug. Exposed wooden beams and modern pendant lights highlight the ceiling. In the background, an open-concept kitchen is partially visible, showcasing a clean, renovated design.
Loft in Kansas City
4.96 out of 5 average rating, 263 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!

Top guest favourite
The living area is detailed with a sectional sofa and a black coffee table. A ceiling fan enhances air circulation. A flat-screen television is mounted above a brick fireplace. Natural light filters through the door, leading to an outdoor space, while a dining area is visible in the background.
Home in Blue Springs
4.96 out of 5 average rating, 197 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

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, 128 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, 36 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

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Guest house in Lone Jack
4.9 out of 5 average rating, 349 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 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.

Top 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, 62 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

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  4. Cass County
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