Vacation rentals in Greenwood

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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!

Landing(43M0)- Sleeps 20 + Airway Strip + Hot Tub

Welcome to your next unforgettable getaway! 🏡 The Landing – Luxury 5BR, 4BA estate on 75 acres 🛫 Private airstrip for plane arrivals 🎬 Movie theater with 15 recliners & arcade games ⛳ Indoor putting green, shuffleboard & ping pong 🎣 Two fishing ponds & hot tub under the stars 🔥 Outdoor fire pit & seating, propane grill 🍳 Gourmet kitchen + coffee bar 🛏 Sleeps up to 20 with multiple beds & bonus rooms 💻 High-speed WiFi & private workspaces 🌳 Explore acres of scenic Missouri countryside

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.

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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*

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Oasis w/Pool & Billiards/Stadiums & Midtown Nearby

Designed for groups, this 3-bedroom (total of four beds) home features a multi-level deck, seasonal outdoor pool, and a lower-level recreation room with a billiards table and wet bar. You will find multiple lounge areas equipped with large smart TVs and a Sonos sound system. The main floor offers an open kitchen and living area, while the backyard provides ample space for outdoor dining and gathering around the firepit. Located a short drive from local stadiums and downtown attractions.

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Exquisite Family Haven On 11 Acres

Set in a serene and picturesque location, this exquisite home offers the perfect balance of luxury and comfort with a country feel. With space for up to 11 guests, this home is an ideal retreat for families and small goups. The gourmet kitchen is fully equipped for any culinary endeavor, with a huge island for family gatherings. The outdoors is where this property truly shines. This finely manicured 11 acres provides walking trails, 3 patios and privacy for a peaceful retreat.

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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.

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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

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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.

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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.

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!

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Hot Tub • Soaking Pool • 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, bunk beds, (seasonal) soaking pool, hot tub (year around) 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.