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.

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.

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.

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.

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.*

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.

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