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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Guest favourite
A gravel drive winds through green grass and trees, leading to the guest apartment and other structures on the 18-acre property. Bright sunlight illuminates the scene, highlighting the natural surroundings and the peaceful setting.
Flat in Oak Grove
4.89 out of 5 average rating, 137 reviews

Private, quiet. I-70 axcess. 23 minutes to KC.

Sleep peacefully in this 600 square foot fully furnished guest apartment located off I-70 frontage in Oak Grove on 18 acres with 2 ponds and rolling pasture. A gravel drive leads to the property where you'll have a concrete parking place and a step-free, pavestone walkway to the front door of the apartment. Rest soundly on a queen size Tuft n Needle mattress in a bedroom with room darkening shades and various pillows to satisfy your comfort. Fully equipped kitchen, laundry room, 2 smart TVs.

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.
Guest house in Lee's Summit
4.9 out of 5 average rating, 619 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!

Guest favourite
A well-arranged private lounging area features a spacious couch adorned with decorative pillows. Natural light fills the space through two large windows, revealing expansive outdoor views. A room divider showcases decorative items and plants, contributing to the overall homey atmosphere.
Farm stay in Oak Grove
4.89 out of 5 average rating, 109 reviews

LOFT Guest Unit Hidden Acres

Located safely just outside the city, in the peaceful serenity of the beautiful countryside. Come stay with us, on the family farm where you will find acres of natural pasture where goats graze and chickens roost in the farmyard. Tucked away and surrounded by many privacy trees the property is breathtaking, relaxing, a place of safety, yet not too far away from town and popular destinations. **5 yrs of professional administrative B&B hosting/hospitality experience. Family Friendly!

Top guest favourite
The historic home features blue siding and white trim, framed by green trees. A welcoming front porch is adorned with hanging planters, and the fenced yard offers a touch of privacy. The entrance is marked by red doors, inviting guests to explore the interior.
Home in Liberty
4.95 out of 5 average rating, 436 reviews

Location! Upscale Historic home w/Chef’s Kitchen

Just steps off Downtown Historic Liberty Square, this updated 1890 home offers guests an upscale luxury experience. Be pampered in the comfortable master suite & enjoy a spa-like experience w/ large clawfoot tub, Carrera Marble shower. Chef’s kitchen includes many amenities. Enjoy meals at the large quartz island. Large private deck. Chaise couch in the living room. Home is divided into complete and private apartments. Each guest has their own entrance and no shared spaces. Wine included!

Superhost
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, 139 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 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
4.95 out of 5 average rating, 166 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 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, 618 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 bright living area features large windows that provide views of greenery and the outdoors. A cozy sofa is positioned across from a small table, with a light-furniture accent chair nearby. Soft lighting enhances the space, creating a relaxed atmosphere.
Guest suite in Union Hill
4.98 out of 5 average rating, 165 reviews

Warm & Curated Retreat, New Build Carriage House

🪴🛌 Your space: the coizest apartment, thoughtfully designed to be where you want to rest and recharge. 🚶🏡 The neighborhood: Martini Corner is a block away w great food, including new Noka, Japanese farm-to-table spot. Local roasting coffee shops Filling Station & Billies Groceries are short walks. 🚙 🚗 Central location: CROWN CENTER - 3 min drive POWER & LIGHT DISTRICT - 5 min PLAZA - 8 min ARROWHEAD & KAUFFMAN STADIUM - 12 min

Guest favourite
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.
Guest house in Lone Jack
4.92 out of 5 average rating, 322 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
4.92 out of 5 average rating, 157 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
4.96 out of 5 average rating, 116 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
A modern studio suite features a spacious bed with crisp white linens and a cozy reading chair beside it. A kitchenette is visible in the background, equipped with a microwave and mini-fridge. Soft lighting complements the neutral decor, creating a welcoming atmosphere.
Guest suite in Grandview
4.83 out of 5 average rating, 130 reviews

Couples or Solo Travelers - Modern Guest Suite

Guests love the convenience and ease of this modern studio suite w/ separate entrance, privacy gate & parking! Has own heating unit & A/C so you can control the temperature to your liking. This walk-out suite is located on the corner of our house, there's a bedroom above it, so you may hear occasional footsteps, sound generally hasn’t been a problem for any guests that have stayed here.

Popular amenities for Pleasant Hill holiday rentals

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  2. United States
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  4. Cass County
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