Holiday rentals in Prairie

Relaxing Retreat in Lee's Summit | NO Cleaning FEE

Welcome to our spacious 4-bedroom home in the charming, tree-lined neighborhoods of Lee's Summit, just a short drive from Kansas City. Whether you're visiting family, attending a sports tournament, hosting a weekend getaway with friends, or simply looking for a peaceful escape, our home is the perfect spot to relax and recharge. Noteworthy: ~0.4 miles - grocery stores, coffee shops, and high-end restaurants. ~2.3 miles - St. Luke’s East Hospital. ~12.5 miles to Kauffman and Arrowhead Stadiums.

Value · Family · Kitchen

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!

Family · Location · Walkability

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!

Value · Family · Access

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. Must have your own cable to plug in.

Location · Family · Grill

Imagine Dolly & Elle Woods Plans your GIRL TRIP

Sleeps 12 | 5 Bedrooms | 3 Bathrooms | 8 beds WALK TO SHOP, DINE, PLAY Grab your friends & find an excuse to celebrate in this dreamy space! Thoughtfully curated house with: GLAM ROOM Spa room Stocked kitchen Patio w/ seating & yard games 4-min walk to charming Downtown Lee’s Summit - locally owned boutiques, restaurants, bars, coffee shops, yoga studio, spa services, live music & so much more! Short drive to downtown KC, OPKS, T-Mobile Center, Power& Light Dist, GEHA Stadium, WORLD CUP

Family · Location · Layout

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*

Value · Family · Decor

Nostalgic and charming condo with rooftop patio

Our condo is located in the heart of beautiful and award winning downtown Main Street in Lee’s Summit, MO. Walk to local shops and restaurants. It’s on the 2nd floor of an historic site with the most amazing rooftop patio and the best views of downtown Lee’s Summit. Three large bedrooms and 2 full bathrooms. Large, well equipped kitchen and large living room with work station. Relax in comfort and sophisticated style. Only 15 miles to stadiums and 20 miles to downtown KC.

Location · Family · Getting around

Lee’s Summit Luxury: 4 King Beds, Pool, Hot Tub

Inside, you’ll find upscale finishes, a beautiful kitchen for cooking and gathering, and eight smart TVs for easy downtime. Outside, enjoy a screened-in porch, and a private pool + hot tub setup that makes this home feel like a personal resort. Sleeping for up to 10: four bedrooms feature King beds, plus an elevated Queen air mattress that’s best set up in the downstairs living room (open-area sleeping). The bedrooms have ceiling fans and walk-in closets.

Location · Family · Bathroom

Stay at Whispering Pines

Whispering Pines in Lee's Summit Missouri offers a nature-framed retreat with city convenience. Wake to quiet trees, unwind in stylish, comfortable spaces, and get everything you need for work and rest—strong Wi-Fi, full kitchen, laundry, and seamless self-check-in. Great for couples, families, and business travelers. Central to local parks, lakes, employers, and dining. Clean, dependable, and thoughtfully hosted for a stress-free stay.

Family · Location · Breakfast

OneNinth-Luxury Downtown Retreat

Experience comfort & style in this spacious 4-bedroom, 6-bed retreat near Downtown Lee’s Summit. Perfect for families or professionals, it boasts 2 living spaces, 5 Roku TVs, a fully stocked kitchen, & a pet-friendly upstairs. Enjoy the private yard, outdoor lounge, front porch swing, & basement games. Located in a quiet cul-de-sac, it’s close to shops, bars, & restaurants. Ideal for getaways, holidays, work trips, or stay-cations!

Value · Family · Access

Family Fave_PutPut_Sleeps 10_Near DT LS Walkable

Just steps from Historic Downtown Lee’s Summit, Bayles Bungalow is a relaxing getaway for families and groups. Walk a few blocks to shops, local restaurants, and nightlife, or stay in and enjoy the backyard putting green, horseshoes, and board games around the table. There’s something for everyone. Experience Kansas City hospitality in a safe, inclusive home that welcomes guests from all backgrounds.

Family · Location · Cleanliness

Cozy downtown cottage

This cute cottage is in the heart of historic downtown Lee's Summit, a short walk from great restaurants, coffee shops, bars, and entertainment. It has a fully functional kitchen, and living room, mature trees, 10-foot ceilings, and a relaxing vibe. You’ll love the neighborhood, the great kitchen, and the coziness, all while being situated within easy highway access to Kansas City.

Location · Family · Decor