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.

World Cup Kansas City | Cozy Home Near Lake

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.

Secluded Silo

Peaceful unique place in the valley where a rooster crow is all you will hear in the morning. Drink coffee on a private deck that overlooks the koi pond with a peaceful fountain. Short drive to I-435 and I-35. About half hour drive to Royals and Chiefs stadiums, downtown KC and Kansas speedway! Minutes from the bike and walking trails that circle Smithville Lake! Caution- steep narrow stairs inside. Please use the outside stairs to carry luggage inside to the bedroom quarters.

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

Comfy and Colorful in KC

Just 15 minutes from downtown and 20 minutes from the airport, this comfy retreat is the perfect launchpad for your Kansas City adventure. With a king bed in one room and two XL twin beds is the second, this spot is ideal for families, friends, or colleagues. Whether you're here for a weekend or a longer stay, you'll feel right at home. Your friendly hosts are just a message away—happy to offer local tips and insider favorites to help you experience the real KC.

Skyline | Hot tub | Rooftop Patio | Amazing Views

Hot tub, fire pit, rooftop patio and amazing views of the KC Skyline! Brand new home, with comfortable king size beds, 3 tv's and modern decor. Outdoor grill, picnic table, wood fire pit and rooftop gas fire pit. Hammocks, corn hole and board games. After booking, guests are required to complete a renter’s agreement and provide a valid government-issued photo ID prior to check-in. This is required for all guests without exception.

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!

Fire Pit + Backyard Family Friendly

Enjoy S'mores by the fire pit in this newly renovated home. If you are in town for a special event or relocating to Kansas, no hotel will be able to meet your needs like this home. We welcome pets and have plenty of room for large families. We are located in North Kansas City, 10 minutes from Downtown and 15 minutes from the KC Airport. ♥Hi-Speed 1G Internet & Work Space ♥Immaculately Clean - Guaranteed! ♥Fire Pit w/ Backyard

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.