
Holiday rentals in Oakwood
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Top-rated holiday rentals in Oakwood
Guests agree: these stays are highly rated for location, cleanliness and more.

Serene Retreat in Kansas City!
This is the place to unwind in peaceful solitude NO PARTIES police will be called. 4 GUESTS MAX. (5.0 to Book) FIRM. No smoking Our meticulously remodeled Airbnb nested in the heart of nature, offering a peaceful retreat amidst a plethora of outdoor recreational facilities. This distinctive property is neighboring a park, basketball court, playground, walking trail and a picnic area, providing a harmonious blend of tranquility while 10 mins to the airport, downtown, neighboring both KCK & KCMO

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.

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

𒊹︎Private Speakeasy Suite featured on KC Today𒊹︎
Want to stay in a gorgeous 100+ year old speakeasy with endless charm and character? This one-of-kind stay gives you an incredible location steps away from downtown! We’ve been featured on best of KC and KC Today for the most unique stays on Airbnb. The building is old but been updated with every modern amenity. Fireplace, tufted sofa, and optional champagne service. The Speakeasy Suite gives you hotel amenities at an amazing value with prime location complete with a speakeasy entry!

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.

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 ~ Sleep 14
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!

Private peaceful very secluded!
The whole group will be comfortable in this spacious and unique space. Peaceful space in the valley where a rooster crow is all you hear in the morning. Have coffee on the dock while feeding koi in the koi pond! Off the beating path of traffic. Short drive to I 435 and I 35. About a half hour drive to Royals and Chiefs stadiums, downtown KC and Kansas speedway! Minutes from the bike and walking trails that circle Smithville Lake!

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!

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.
Popular amenities for Oakwood holiday rentals
Other great holiday rentals in Oakwood

Riverside 2BR Near Downtown KC | Self Check-In

Basement Apart. Near LDS Temple

4865 two bedrooms/15 min from MCI/downtown KC

A home away from home - family friendly, central

Farmhouse Gone Game Room

Cozy Kansas City Home w/ Yard - 9 Mi to Dtwn!

Cul-de-sac Coolness

The 420 House
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- GEHA Field at Arrowhead Stadium
- Oceans of Fun
- Kauffman Stadium
- Kansas City Zoo
- LEGOLAND Discovery Center Kansas City
- The Nelson-Atkins Museum of Art
- Snow Creek Ski Area - 2022 OPEN WEEKENDS
- Kansas City Convention Center
- Jacob L. Loose Park
- Negro Leagues Baseball Museum
- T-Mobile Center
- Union Station
- Legends Outlets Kansas City
- University of Kansas - Lawrence Campus
- Uptown Theater
- Midland Theatre
- Kauffman Center for the Performing Arts
- Overland Park Arboretum & Botanical Gardens
- National World War I Museum and Memorial
- Science City at Union Station
- Hyde Park
- Crown Center
- Bartle Hall
- Children's Mercy Park




