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.

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.

Close to Downtown & Stadium, Huge Yard, RV Parking

Great for families or anyone looking for a quiet, safe neighborhood. - Google Fiber - Fully fenced yard. - Off street parking - Close to the interstate - Only 15 minutes of downtown, Worlds of Fun, Oceans of Fun, & Kaufman & Arrowhead stadiums World Cup Addons Grocery stocking: $100 service fee + grocery cost Early check-in / late checkout (when available): $75 each Relax on the porch while watching your kids play in the fenced-in yard or play fetch with your dog. Non-smoking home.

Hip Downtown Loft Walk to River Market and DT

Live Like a Local in the Heart of KC! 1 bedroom loft, perfectly located in River Market within walking distance of top restaurants, bars, coffee shops, unique boutiques, and the farmers market. Whether you're here for work or play, this space offers the ideal blend of comfort and convenience. Under a 15 min drive to Arrowhead Stadium. ✔ Fully stocked kitchen ✔ Smart TV & free Wi-Fi ✔ Rooftop deck & fitness center ✔ Walkable (Downtown and Convention Center are a 15 min walk or less)

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.

High-End Hobbit House

Experience a luxurious and cozy stay in our unique Hobbit House, a private studio basement apartment, part of an historic home built in 1890. Located just steps from the Historic Downtown Liberty Square, walkable to William Jewell College and a short 20-25 minute drive to downtown Kansas City. The property offers the perfect blend of historic charm and modern comfort. While more suited to guests under 6'1" this enchanting retreat provides a distinctive and memorable experience.

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!

Sleeps 8_Near Arrowhead_4BR_Pets Ok_FIFA 26

Just 12 miles from Arrowhead Stadium, perfect for FIFA World Cup 2026! This recently constructed house is furnished with brand new items and situated in close proximity to several of Kansas City's renowned attractions. If you plan to visit Worlds/Oceans of Fun, this property is the ideal location. It is a suitable option for family holidays, corporate accommodations, or a romantic escape.

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.