Vacation rentals in Greenwood

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Top-rated vacation rentals in Greenwood

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Top guest favourite
A spacious sleeping area features a queen-size bed dressed in a turquoise coverlet, complemented by decorative pillows. Natural light floods through a nearby window covered with light curtains. A wooden dresser and bedside table add warmth to the room, while framed artwork enhances the decor.
Guesthouse in Westwood
4.99 out of 5 average rating, 679 reviews

Westwood cottage in garden setting

This 400 sq. ft. guesthouse (studio) on a historic property in Westwood, KS has recently been fully renovated and furnished. It has a completely equipped kitchenette, comfortable living area, along with a queen-size bed. The guesthouse also includes a washer/dryer off the kitchenette. The guesthouse is a separate dwelling located on a half an acre property which includes the original farmhouse built in 1889 - the guesthouse added in 1920. Westwood, Kansas is 2 miles from the Country Club Plaza.

Superhost
The exterior of the modern home features a striking façade with a mix of white cladding and natural wood accents. Expansive glass windows allow natural light to flow inside. A small outdoor seating area with wooden chairs complements the inviting entrance, surrounded by greenery.
Home in Downtown Kansas City
4.89 out of 5 average rating, 122 reviews

Modern Madison - Near Downtown & Crossroads

Are you looking for a one-of-a-kind stay? Our property is like no other. Awarded by the prestigious American Institute of Architects and featured in various magazines, it's a modern, minimalistic and sustainable home. Everything is fully electric - powered by solar panels - reducing carbon footprint. It's located in the trendy Westside neighborhood, just steps away from Downtown & Crossroads. Make your stay a memorable one & enjoy the Modern Madison experience. Thank you for considering us!

Guest favourite
Barn in Greenwood
4.91 out of 5 average rating, 215 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*

Superhost
A charming exterior view of a historic home features a dark blue facade with white trim. A covered porch is visible, equipped with railings and a rocking chair. The yard is adorned with fallen leaves, and large windows allow natural light into the rooms.
Townhouse in Pleasant Hill
4.9 out of 5 average rating, 141 reviews

Rebecca's Retreat Historic Downtown Pleasant Hill

Stay in private unit in Historic Downtown Pleasant Hill, MO!!! 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, bath and kitchenette. Watch a movie in the spacious living area or curl up with a book. In suite laundry provided for your convenience. Kitchenette provides fridge, microwave, coffee maker(and supplies), toaster, dishes and basic cooking utensils.

Guest favourite
The entrance of the Bohemian Lodge is illuminated at dusk, with a winding pathway leading to the front door. A cozy seating area is visible, framed by lush greenery and illuminated by soft garden lights along the path.
Guest suite in Buckner
4.94 out of 5 average rating, 163 reviews

MILO FARM-Sacred Kansas City Retreat

MILO FARM - SACRED LAND sits east of Kansas City & is a nature retreat w/ a cedar forest, a hardwood forest, 2 ponds, bohemian lodge, art studio, pool, barn, miles of trails & whimsical camping spots.  Pet and feed the farm animals while you are here! Guests have lower level of the lodge to themselves with 2 suites (with private baths), rec room, bar area, laundry, steam sauna & rock sauna, play room & patio.  Milo Farm is located just 30 minutes from KC. More info on MiloFarm.com

Top guest favourite
A warm hearth room is presented with a brick fireplace, featuring an electric insert. A patterned armchair and a stylish side lamp are positioned nearby. Light artwork adorns the wall, while a coffee table and shelves with books and decorative items complete the inviting space.
Home in Independence
4.99 out of 5 average rating, 126 reviews

Family Friendly - Sleeps up to 7 -Wshr/Dryr

Welcome to the 'Enlightened Retreat' . 3 bedroom home located minutes to Arrowhead and Geha Field for the Royals and Chiefs fans. We designed the Retreat to the perfect vacation for the mind, body and soul. Enjoy all the sights and sounds Kansas City has to offer and then come back to a relaxing atmosphere where you can recoup, rejuvenate and relax. Stay for the weekend or all week. We think the "Enlightened Retreat' is just what you need. Be well and we hope to see you soon.

Top guest favourite
Home in Fairway
5 out of 5 average rating, 121 reviews

Prestige-Stunning Home W/Game Room+ Mins to Plaza

⭐ Fully renovated 3BR home in Fairway, KS — minutes from KC attractions ⭐ Main-level primary suite with spa-style en-suite bath + clawfoot tub ⭐ Open-concept kitchen with quartz counters + full coffee bar ⭐ Cozy living room with gas fireplace + Smart TV ⭐ Upstairs game room with Xbox + lounge space ⭐ Private office, exercise area, and landscaped backyard ⭐Conveniently located less than 5 minutes from The Shops of Prairie Village and roughly 10 minutes from the Country Club Plaza!

Top guest favourite
Condo in Grain Valley
4.96 out of 5 average rating, 301 reviews

A little touch of home.

Our cozy townhome is 2 bedroom 2.5 bathroom with about 1200 square feet. We replaced the sofa sleeper 12/6/2025 for the comfort of 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
The living area features a comfortable sofa and an armchair next to a round coffee table. Natural light enters through multiple windows with blinds. A fireplace adds warmth to the space, which is carpeted and includes a dining area visible in the background.
Guest suite in Blue Springs
4.95 out of 5 average rating, 117 reviews

WoodsideView/ Private Suite

Relax in this quiet peaceful retreat. Spacious suite with one bedroom and second bed tucked away in adjacent room. Large bathroom with jacuzzi tub and shower. Kitchenette with microwave, toaster, coffee maker and full size refrigerator. No stove/oven. Private entrance and on-sight parking. Quiet suburban neighborhood close to lakes and trails. Hosts live upstairs and are available to help make your stay a memorable one. No smoking, no unregistered guest. Quiet hrs 10pm - 7am

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, 679 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, 122 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.

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
4.86 out of 5 average rating, 119 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 vacation rentals

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