Holiday rentals in Greenwood

LS Bungalow in downtown Lee's Summit

Kick back and relax in this calm, stylish space. This place is exquisite. Easy Access to the BIG SOCCER GAMES. 5 minute walk to FIFA transportation. Great for couples, business, vacation, or just visiting Private, parking. You will love this location. You can park and never have to get back in it until you go home. Just steps from nationally ranked Downtown Lee's Summits restaurants, shops and bars, You're 20 min from downtown Kansas City and 15 min from Royals Kauffman & Arrowhead Stadium

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.

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!

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*

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.

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

Lone Jack Cabin - Studio Suite

Beautiful private log cabin suite, conveniently located just east of the Kansas City Metro with great highway access. Close to wedding venues: Lone Summit Ranch, Powell Gardens and Stonehaus Winery. All the comforts of home! The suite features a king bed, sitting area with gas fireplace, private bath with shower, whirlpool jetted tub and kitchenette. The kitchenette includes a full-size refrigerator, small stove/oven, microwave and sink. Electric grill on private deck.

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.

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.

The Summers Silo

The Summers Silo is truly a one-of-a-kind tiny home carefully crafted from a converted grain bin. This fully furnished 1-bed, 1-bath retreat features warm pine floors, a private balcony, and a grill for outdoor dining. Set on 13 peaceful acres with access to scenic trails, this cute and unique retreat is perfect for relaxing, unplugging, and enjoying nature under the stars.

Cedar Hollow Bungalow, Lee’s Summit MO

This beautiful cottage-style bungalow has two bedrooms with queen size beds and one bath. This home has been completely renovated and is located on its own 1 acre plot with private parking and is part of a larger 20 acre farm. Enjoy waking up to the sounds of the birds, seeing other wildlife and a wooded walking trail beside a rocky stream in your own private get-a-way.