Holiday rentals 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
A spacious living area features exposed brick walls and wooden ceilings, enhancing the home's character. A comfortable gray sectional sofa is positioned across from a media console, with a stylish green chair nearby. Bright natural light fills the room through large windows framed with plants.
Apartment in Westside North
4.97 out of 5 average rating, 636 reviews

Historic, Industrial Flat in the Heart of KC

Live the true Kansas-Citian lifestyle during your stay at this sparkling clean, private, and completely renovated 120-year-old brick beauty! Gorgeous hardwood floors, exposed brick walls, 11' exposed wood ceilings, 2 private decks, large gourmet kitchen, luxurious full bathroom, spacious master bedroom, and cozy 2nd bedroom. Located in the historic Westside of Kansas City; Walk seconds to neighborhood hot spots & minutes to KC's highlights: Crossroads, Street Car, Downtown & Convention Center.

Guest favourite
A well-lit living room features a comfortable sofa adorned with decorative pillows. A round coffee table sits on a textured rug, while a ceiling fan provides airflow. The room showcases art decorations, shelves, and a clock, with an entrance door leading to the outdoor area.
Home in Grandview
4.87 out of 5 average rating, 114 reviews

Cozy Home: Close to Everything! Pet Friendly!

Quiet neighborhood conveniently located near KC attractions! We offer a spacious well lit home away from home. Our well stocked kitchen has a sliding glass door that leads to our spacious backyard featuring a patio where friends & family can grill & where kids can play in their own playground. The master bedroom has a king bed and attached bathroom. Our queen bed, fun 3 bunk bed and 2 futon beds in the living room offer guests many more sleeping options! Note: we do not accept local guests.

Superhost
The entrance features a white railing leading up to a covered porch. A solid door, flanked by a window on one side, is highlighted by a wall-mounted light fixture. The exterior is painted a darker shade, contrasting with the white trim.
Townhouse in Pleasant Hill
4.88 out of 5 average rating, 101 reviews

Lauren's Loft in Historic Downtown Pleasant Hill

Stay in private unit in Historic Downtown Pleasant Hill! Suite is located right on the Rock Island/Katy Trail! Beautiful 1920's home renovated into 3 private suites. This suite features a private bedroom with king memory foam bed, a loft with 2 twin beds, bath and kitchenette. Relax in the comfy living room watching TV or reading. In suite laundry provided for your convenience. Kitchenette provides fridge, microwave, coffee maker(and supplies), toaster, dishes and basic cooking utensils.

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.
Guest house in Lee's Summit
4.9 out of 5 average rating, 630 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
A cozy living area features a brown leather couch paired with a stylish side table and an eclectic floor lamp. A compact dining table with metal chairs is positioned near a large mirror, while natural light filters through the windows, enhancing the inviting space.
Home in Lee's Summit
4.92 out of 5 average rating, 138 reviews

Charming Mid-century Home DTLS

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!

Top guest favourite
A broad driveway leads to a spacious building featuring a mix of brick and blue siding. Two garage doors are visible, framed by landscaped green areas and decorative fencing. The serene surroundings are complemented by trees in the background, creating a peaceful entrance.
Barn in Greenwood
4.91 out of 5 average rating, 203 reviews

Cozy private cottage/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
Apartment in Grain Valley
4.95 out of 5 average rating, 259 reviews

A Place Like Home

Our cozy townhome is 2 bedroom 2.5 bathroom with about 1200 square feet. We replaced the sofa sleeper and hope that is comfortable for your extra guest. We are located a few blocks off I-70 and can be at most area attractions, shopping and dining in less than 30 minutes. Kauffman & Arrowhead Stadiums (16 miles 18 minutes) Cable Dahmer Arena (9.6 miles 14 minutes) Sprint Center (23 miles 23 minutes) KC Zoo & Starlight Theatre (24 miles 27 minutes) Worlds of Fun (26 miles 28 minutes).

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, 656 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 a patterned couch alongside a light wood coffee table. Two lamps provide soft lighting, illuminating the hardwood floors. A chair and a folding chair offer additional seating, while wall art adds color and interest. Windows allow natural light to fill the space.
Guest suite in Lee's Summit
4.97 out of 5 average rating, 113 reviews

Vintage Space! Downtown Lee’s Summit

Super retro style upstairs apartment! This is the top story apartment of a home built in 1898. It is just a 5 minute walk to downtown Lee's Summit! It is close to restaurants, coffee shops, family-friendly activities, shopping, bars and a whole slew of entertainment. You’ll love the space because of the location, the ambiance, and the people. It is good for couples, solo adventurers, business travelers, and families (with kids).

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, 121 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.

Guest favourite
A modern studio suite features a spacious bed with crisp white linens and a cozy reading chair beside it. A kitchenette is visible in the background, equipped with a microwave and mini-fridge. Soft lighting complements the neutral decor, creating a welcoming atmosphere.
Guest suite in Grandview
4.83 out of 5 average rating, 137 reviews

Couples or Solo Travelers - Modern Guest Suite

Guests love the convenience and ease of this modern studio suite w/ separate entrance, privacy gate & parking! Has own heating unit & A/C so you can control the temperature to your liking. This walk-out suite is located on the corner of our house, there's a bedroom above it, so you may hear occasional footsteps, sound generally hasn’t been a problem for any guests that have stayed here.

Top guest favourite
The front exterior of a charming two-story house is featured, showcasing a red front door framed by flower planters. A brick walkway leads to the entrance, with surrounding landscaping that includes colorful flowers and pumpkins. A porch with seating is visible, welcoming guests.
Home in Blue Springs
4.85 out of 5 average rating, 111 reviews

Two story tiny house bungalow!

Take it easy at this unique little getaway! Top level offers a cozy bedroom with sitting area, bathroom, and laundry. Open main level has kitchen and living area plus 1/2 bath! Relaxing outside area with table and grill! Only one block from downtown Blue Springs where you have Scout Coffee, Brewers Sports Bar, Pizza Shoppe, Bean Counter Cafe and much more!

Popular amenities for Greenwood holiday rentals

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