Holiday houses in Greenwood

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Top-rated holiday rentals in Greenwood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Grain Valley
5 out of 5 average rating, 88 reviews

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.

Top Guest favourite
A log cabin is reflected in the calm waters of a private lake, framed by lush greenery. Large windows illuminate the interior, while the structure's pitched roof and outdoor seating area create a welcoming environment for relaxation.
Home in Pleasant Hill
4.98 out of 5 average rating, 52 reviews

The Cabin at Big Creek

Ultimate Seclusion Nestled away on 120 acres this fully updated log cabin sets on a 5 acre private lake with a rolling creek. Approximately 20 miles from Arrowhead (GEHA Field) where the World Cup will be held. 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

Guest favourite
The guest house exterior is framed by lush trees, featuring a light brown siding with a shingled roof. Large windows allow for natural light, while a welcoming front porch enhances accessibility. A two-car garage is situated to the right of the entrance.
Home in Peculiar
4.91 out of 5 average rating, 226 reviews

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.

Superhost
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.
Apartment in Oak Grove
4.89 out of 5 average rating, 163 reviews

Private, quiet, safe. I-70 access. Close 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.
Guesthouse in Lee's Summit
4.91 out of 5 average rating, 653 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!

Top Guest favourite
Barn in Greenwood
4.92 out of 5 average rating, 252 reviews

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*

Guest favourite
Guest suite in Lee's Summit
5 out of 5 average rating, 7 reviews

South KC/ Lee's Summit spacious charmer!

Whether traveling for business or with family you'll will be close to everything when you stay at this centrally-located place. Lee's Summit boasts several shopping, restaurants and activities but also located on the south suburban side of the Kansas City metro area keeping you close to all the action in a safe family-friendly neighborhood. You'll have everything you need in this space with two bedrooms, full kitchen, laundry use and free on-street parking. Located in daylight basement.

Guest favourite
Home in Blue Springs
4.92 out of 5 average rating, 60 reviews

The Cozy Escape

Welcome to your cozy home away from home! This comfortable retreat is just 5–6 minutes from Lake Jacomo and surrounded by plenty of walkable nearby stores, restaurants, and local conveniences. Perfect for families, couples, or solo travelers, the home features a 2-car garage, easy highway access, and a warm, inviting atmosphere designed for relaxation. Whether you’re here to unwind, explore the outdoors, or visit Kansas City, you’ll have everything you need for a comfortable stay.

Top Guest favourite
A modern A-frame home is showcased, featuring a striking green exterior and a sloped roof. A spacious deck with black railings is accessible by a set of stairs. The property is surrounded by landscaped grass and trees, contributing to a serene environment.
Home in Raymore
5 out of 5 average rating, 48 reviews

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.

Superhost
Townhouse in Lee's Summit
4.82 out of 5 average rating, 137 reviews

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.

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, 732 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 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
4.95 out of 5 average rating, 136 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.

Popular amenities for Greenwood holiday rentals

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  2. United States
  3. Missouri
  4. Jackson County
  5. Greenwood