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.

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Top guest favourite
Home in Grain Valley
5 out of 5 average rating, 87 reviews

Soaking Pool • Hot Tub • 27 min to Arrowhead

Escape to KCcabin — a modern, secluded retreat in the Lake Lotawana area (no lake access). This new-build hideaway offers 2 bedrooms plus bunk beds, NEWLY ADDED soaking pool and hot tub with wooded views, spacious deck & grill, 65" smart TV, WiFi, washer/dryer, and a workspace with standing desk. Just minutes to dining, marinas, and only 30 min to downtown KC. Perfect for families, couples, or remote work getaways. If you'd like to view a walkthrough video, message me and I can send you a link.

Superhost
Home in Gladstone
4.77 out of 5 average rating, 113 reviews

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

Top guest favourite
An inviting kitchen features wooden cabinetry and a spacious countertop. A compact table for two is positioned near a sliding glass door, leading to a view of the outdoors. Essential appliances are neatly arranged, contributing to a functional cooking space.
Flat in Kansas City
4.95 out of 5 average rating, 914 reviews

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.

Guest favourite
A light-filled living area features a pair of dark leather sofas adorned with orange accent pillows. A decorative rug with a neutral pattern lies beneath, while a floor lamp and a wall-mounted TV provide functional comfort. Natural light streams through large windows covered by sheer curtains.
Home in Kansas City
4.91 out of 5 average rating, 265 reviews

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.

Superhost
Home in Gladstone
4.91 out of 5 average rating, 176 reviews

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.

Superhost
Home in Kansas City
4.82 out of 5 average rating, 22 reviews

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

Top guest favourite
Home in Kansas City
5 out of 5 average rating, 18 reviews

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.

Superhost
Flat in Riverside
5 out of 5 average rating, 3 reviews

4861/Near Hwy 15 min From MCI airport &Downtown/KC

Stay in the heart of the Kansas City area with easy access to major highways, downtown attractions, shopping, dining, and entertainment. Just minutes from the airport, this cozy home is perfect for business travelers, families, and visitors. Located on a quiet cul-de-sac, it offers a peaceful retreat with a nearby park for children and scenic walking trails behind the property. Enjoy comfort, convenience, and a central location for exploring Kansas City.

Guest favourite
The split-level home features a modern exterior with a combination of wood accents and a light blue facade. A paved driveway leads to the front entrance, framed by well-maintained green grass and landscaping. Large windows and a welcoming front door create an inviting appearance.
Home in Gladstone
4.89 out of 5 average rating, 249 reviews

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!

Guest favourite
A spacious bedroom features a large bed dressed in white linens, complemented by decorative pillows. Two framed prints adorn the walls, and a wooden dresser sits adjacent, providing storage. A stylish bench rests at the foot of the bed, with soft lighting from bedside lamps.
Home in Kansas City
4.94 out of 5 average rating, 109 reviews

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

Guest favourite
Home in Houston Lake
4.91 out of 5 average rating, 43 reviews

Peaceful 3BR Lake Retreat | Fire Pit & Fenced Yard

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. Perfect for everyone looking for a peaceful stay while visiting KC.

Top guest favourite
A charming 1930's home is surrounded by vibrant fall foliage, with a stone and wood exterior. The front yard is blanketed with colorful fallen leaves, and a mailbox stands at the end of a paved driveway leading to the garage.
Home in Parkville
4.95 out of 5 average rating, 66 reviews

Cozy Bluegrass Cottage

Come and relax at this peaceful place to stay. Central location- 15 minute drive to MCI Airport, or Downtown KC. Enjoy the Locals- Old town Parkville offers shopping, coffee shops, dining French, Irish, and Italian. If you prefer to BBQ at home, pick up farm fresh meat at the KC Cattle Company. Several walking trails, children parks, and dog parks. Take the bikes for a ride along the river to enjoy the best sunsets!

Popular amenities for Oakwood holiday rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Clay County
  5. Oakwood