Vacation rentals in Greenwood

Soaking Pool • Hot Tub • 27 min to Arrowhead

Escape to KCcabin — a modern, secluded retreat in the Lake Lotawana area (no lake access). This new-build hideaway offers 2 bedrooms plus bunk beds, NEWLY ADDED soaking pool and hot tub with wooded views, spacious deck & grill, 65" smart TV, WiFi, washer/dryer, and a workspace with standing desk. Just minutes to dining, marinas, and only 30 min to downtown KC. Perfect for families, couples, or remote work getaways. If you'd like to view a walkthrough video, message me and I can send you a link.

Charming Getaway just south of Kansas City

*This is a smoke-FREE property* Do you have fond memories of staying at grandma's house as a kid? Then you'll love our spacious 1200 sq foot guest house on our beautifully treed, secluded 3 acre property, complete with hobby farm animals. Whether you are coming to visit the KC Metro area or looking to get away from the city, we have you covered. Located just off of I-49 highway, we are less than 30 minutes from the Country Club Plaza, Kauffman and Arrowhead Stadiums, and Downtown Kansas City.

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*

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.

The Cabin at Big Creek

Ultimate Seclusion Nestled away on 120 acres this fully updated log cabin sets on a 5 acre private lake loaded with fish with a rolling creek. Approximately 20 miles from Kansas City. 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

Nick's Place

*This is a smoke-FREE property* Need a home away from home? Come stay in our beautiful, fully renovated A-frame home on 3 secluded acres. Whether you are coming to visit the KC area or looking to get away from the city, we have you covered. Located just off 150 Hwy with quick easy access to I-49 Hwy, and 291 Hwy we are 30 minutes from the Country Club Plaza, Kauffman and Arrowhead Stadiums, and Downtown Kansas City. 50 minutes from Kansas City International Airport.

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.

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.

Hummingbird Chateau | Luxury Golf & Nature Retreat

Welcome to Hummingbird Chateau, an elegant English Cotswold-style home in historic Unity Village. Nestled on 1,200 peaceful, wooded acres, this spacious 4-bedroom, 3.5-bath comfortably sleeps up to 14 guests. Relax on private patios around the gas fire pit, or unwind inside a charming, light-filled space. Located minutes from Kansas City and Lee's Summit, it is the perfect setting for family reunions, group stays, and tranquil getaways.

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!

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.

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.