Vacation rentals in Oakwood

Coveted Museum District Stylish Eastlake Victorian

Step into this exquisitely renovated Eastlake Victorian on tranquil Oak St, in Kansas City’s vibrant Southmoreland, steps from Nelson-Atkins, KCAI, Plaza, and Westport. This 3-bed, 2-bath gem boasts soaring ceilings, floating cedar shelves, and a private backyard patio for serene retreats. Enjoy designated parking and a walkable Museum District, just 4 blocks from the Main Street. Blending historic elegance with modern flair, this chic haven promises an unforgettable stay in KC’s cultural heart.

The Kelsey House - Modern, Family-Friendly Space

Bring the whole family to this great place with lots of room for fun! Minutes from the lively river market and downtown. Quick highway and airport access. short drive to many popular recreational and city attractions! - Family and pet friendly (no pet fee!) - Accessible & spacious single-level home - Earthy, artsy and locally-inspired vibes - Many amenities offered to feel like home DOORS: FRONT 36''W with 4''ramp / BDS 29''W / BATHS 23''W 4-Car Driveway. Yard not fenced. ICE NOT WELCOME.

World Cup 2026 | Sauna | Plunge Pool | Tiki Lounge

A 125-year-old bungalow packed with personality. Inside you’ll find curated worldly décor, many lounge spaces, and the house’s most famous feature: the Lucky Kitty Tiki Lounge, a hidden bar built inside the old garage. Outside, relax in the barrel sauna, cold plunge, and stock tank pool, gather around the fire pit, and unwind under the string lights after a night exploring Kansas City. It’s a one-of-a-kind stay just minutes from downtown, the stadiums, and some of the city’s best restaurants.

Location & Luxury in Downtown Liberty

Just steps off Downtown Historic Liberty Square, this updated 1890 home offers guests an upscale luxury experience. Be pampered in the comfortable master suite & enjoy a spa-like experience w/ large clawfoot tub, Carrera Marble shower. Chef’s kitchen includes many amenities. Enjoy meals at the large quartz island. Large private deck. Chaise couch in the living room. Home is divided into complete and private apartments. Each guest has their own entrance and no shared spaces. Wine included!

Cozy in KC Freshly updated & Clean. Self-checkin

This Charming KC home is 20 mins from -Casinos, Power& Light, Westport, Chiefs/Royals Stadium. TO BOOK MUST HAVE 5.0 REVIEWS ONLY. 4 GUESTS MAX- outdoor cameras to monitor the usage. Just trying to respect the neighbors & keep the place nice/new. Near I-35, I-29, hw 70, 71, and 435. Safe location w/plenty of restaurants &shopping nearby. ZERO tolerance for PETS, SMOKING or PARTIES. (will be charged $100) 2 King beds Google Fiber WiFi Easy self check in w/combo messaged to you at 3pm.

Secluded Retreat in the City with 2 Bedroom

Welcome to this secluded retreat in the city. This home rests off the road with an enormous backyard, Featuring, large open yard, tree lined area with a small creek. Sit on the large deck or lounge in the hammock and watch for deer and other wildlife to visit. Corn hole and Mini golf games outside. Inside you will find the home neatly appointed, and designed with bright colors and happy vibes. 2 bedrooms with queen beds await. Relax during your stay with NO required cleaning tasks.

Country Paradise •9 acres•Pool•Rec Center

Welcome to your very own private resort! As you approach the property, you'll be greeted by a beautiful farmhouse-style home that sits on 9 acres, with a 55ft wrap around deck offering sweeping views of the expansive grounds. Pool table, Ping Pong, Shuffleboard, Foosball, Air hockey, Nintendo & Switch. This property is a true gem for those seeking both space & serenity. 17miles-airport, 20miles Downtown KC/ P&L District, 22miles-Chiefs /Royals Stadium, minutes to Smithville Lake.

Latitude 39

This five-bedroom three-bathroom split-level home away from home offers a comfortable haven to relax for groups of friends or large families! The open floor plan between the living room, dining room, and kitchen allows you to spend quality time together. In the living room you’ll find a tv with a YouTube TV subscription, and if you want to spend time outdoors, you'll love the relaxing deck and yard where you can unwind and relax!

WestSide Brick Barn Studio

The Brick Barn Studio is a sweet and peaceful private space on the first floor of a late 19th century Carriage House. Guests enjoy private entry to their accommodation, mini kitchen, shower/bathroom, and laundry, king mattress on a unique built-in bench platform, and a convertible sofa for another guest or two. There is a privacy curtain provided for guests who would like a little separation between the bed and sleeper sofa.

Charming (1) king bed home w/ walkable restaurants

Spacious, bright home for up to 6 guests with self-check-in, fully equipped kitchen, backyard patio, and free parking. Relax with complimentary coffee, Roku streaming, great Wi-Fi, and easy access to walkable restaurants and shops. Perfect for families, business travelers, or weekend getaways. Just 12-15 minutes from Downtown Kansas City in the neighboring suburb of Gladstone! Book your stay!

Sunset House-Near Worlds Of Fun and downtown

Beautiful country home that's in a small quite town, that's next to the big city. Featuring 2 bedrooms and 1 full bathrooms. House sleeps 4 people comfortably. Dogs are allowed but limited to 2 dogs per stay. There is a fenced in back yard for dogs to roam around and play. The house is perfect for a family friendly stay. No one under 25 year of age can book with us

Updated home, FIFA World Cup, Worlds of Fun, Ford

Updated, clean and comfortably furnished 4 bedroom home with fast WiFi, TV, and off street parking. FIFA World Cup Kansas City - Arrowhead Stadium: 13 miles ConnectKC26 Transportation: 1.7 miles FIFA Fan Festival : 9 miles Minutes from Worlds/Oceans of Fun and Ford Kansas City Assembly Plant. 13 miles from Arrowhead/Kauffman Stadium.