Holiday 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.

Little White House at Liberty

Private Little White House Retreat! Standalone studio in Liberty’s quiet Historic District, 2 blocks to Downtown Liberty Square. 23–25 min to Kansas City. EV charging on-site. Enjoy a loaded coffee bar or visit our Coffee Shoppe across the street, then walk to boutiques, restaurants, historic sites. Relax in a peaceful space with a very comfortable queen bed, large TV w/ DIRECTV, full kitchen, walk-in shower, in-unit washer/dryer—perfect for couples, solo travelers, or restful overnight stays.

4bed * Gladstone home * sleeps 10 * near KC

Welcome to our 4 bed 2 bath home in Gladstone (Kansas City North Area)- The perfect place for families, groups or business travelers looking for comfort, space, and a convenient location. You will be close to shopping, dining, entertainment and the best of Kansas City. Downtown Kansas City 14 minutes Worlds of fun 13 minutes KC Union Station 18 minutes Kansas City zoo & aquarium 24 minutes KC Cheifs and Royals statiums 22 minutes Walmart 5 minutes MCI international Airport 17 minutes

Private guest house on 100 acre farm

Relax, visit the animals, hike, explore or venture out at this unique and tranquil getaway. Enjoy sporting events, night life, concerts, plays, ballets, the symphony, family fun parks, nature and unique, small towns and wineries. Minutes from beautiful nostalgic Parkville, which originated as a river port. The arrival of the train ensured the town's survival after the Civil War. Enjoy museums, Union Station, or learn about the history of Kansas City. The “Shanty” is private but so convenient.

Spacious 3BR• Lake Access • Fire Pit • WorldCup KC

Welcome to our quiet lake community vacation home in the heart of Kansas City! Conveniently located near dining, shopping, and popular attractions including the KC Chiefs, KC Royals, and Worlds of Fun. Airport is also just a short drive away. The home features 3 bedrooms with 3 queen beds and a large fenced backyard, with easy walking access to the lake. Guests can fish at the lake, but a Missouri fishing license is required. Perfect for everyone looking for a peaceful stay while visiting KC.

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.

Beautiful Villa Leocadia+ Private Pool + Sleeps 8!

🏡 Villa Leocadia – Your private Kansas City oasis! 🛏 4 cozy bedrooms (1 King, 2 Queens, 1 with 2 Full beds) 🛁 2 full bathrooms with luxury Tommy Bahama products 🍳 Renovated kitchen + coffee bar (Keurig, French press, pour-over) 🛋️ 2 living areas with Smart TVs, board games, and books 🏊 In-ground pool, fire pit, and multiple outdoor seating areas 🌳 Quiet neighborhood near Englewood Park — perfect for relaxing & reconnecting 🚗 Parking allows a max of 3 vehicles

Private Guest Suite Hexagon Room

We offer an entire private lower level with one queen size bed and the OPTION to add a connected private room with a queen bed. A personal driveway with parking, that leads you right to our entry door. Dog Friendly. If you'd like to request the attached additional room, please select "3 or more guests" upon booking. *No cats please, allergic to cats.* *Pets, Emotional Support Animals, and Service Animals must be in the care of an adult at all times.*

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.

Minimalist Modern Strawberry Hill Get-Away Home

Entire, separate entry, second floor studio. Minimalist modern decor, nice clean small space with everything you need. We aim to have your stay be an enjoyable experience, greeting you with a clean home, ensuring you have what you need during the stay, and being available as needed. Approximately 5-10 from downtown KCMO, Power and Light, City Market. Within walking distance of a few local family owned restaurants and bars.

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!