Vacation rentals in Oakwood

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Top-rated vacation rentals in Oakwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The charming exterior of the standalone studio features a covered porch with seating options, surrounded by greenery. The front yard is well-maintained with a grassy area and planters. Large, open windows enhance natural light, creating a welcoming atmosphere.

Home in Liberty

4.97 out of 5 average rating, 100 reviews

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.

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Top guest favorite

A modern kitchen is presented with sleek appliances and ample counter space. Storage options include stylish baskets arranged on shelves. Light wood flooring complements the warm tones of the cabinetry. A well-lit pantry is accessible through double doors, enhancing functionality and organization.

Apartment in Gladstone

4.95 out of 5 average rating, 98 reviews

Cozy 2-bedroom apartment in Kansas City North

Welcome to this enchanting apartment in Gladstone. Be close to it all in this spacious and serene space. Featuring 2 bedrooms with a king & queen bed, perfect for a pleasant stay. Two full bathrooms offer a refreshing experience for guests. Whether you're visiting family & friends or in town for a special event, we have the perfect place for you to rest & reset. Offering amenities like an onsite fitness center/yoga room, heated pool, outdoor kitchen areas, game room, movie lounge, & a dog park.

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Top guest favorite

Home in Liberty

5 out of 5 average rating, 52 reviews

Retro Rambler

Relax with the whole family at this peaceful escape. With 3 bedrooms and 2 bathrooms this ranch style house is the perfect place to stay. Featuring a large fenced backyard, basement game room, relaxing sun room, and fully equipped kitchen. Close access to I-35 makes visiting downtown Kansas City quick and easy! Only 20 minutes to the airport, 10 minutes to historic Liberty Square, 20 to Kauffman and Arrowhead, and 10 to Worlds of Fun. Convenient to shopping, movies, gas and necessities.

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Top guest favorite

Home in Houston Lake

4.93 out of 5 average rating, 55 reviews

Cozy KC Getaway | 3BR Near the 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. The airport is also just a short drive away. The home features 3 bedrooms with 3 queen beds and a large fenced backyard. Located in a beautiful lake community, it’s perfect for everyone looking for a peaceful stay while visiting KC. Self-service Mini Market with snacks & drinks available.

LocationFamilyComfort

Top guest favorite

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.

Apartment in Kansas City

4.95 out of 5 average rating, 924 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.

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Superhost

Home in Gladstone

4.91 out of 5 average rating, 179 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.

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Guest favorite

Tiny home in Smithville

4.9 out of 5 average rating, 82 reviews

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.

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Superhost

Home in Kansas City

4.78 out of 5 average rating, 23 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

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Guest favorite

A comfortable living area is presented, featuring a gray sofa and armchair paired with a black coffee table. Two windows allow natural light to illuminate the space, while a wall-mounted television and decorative wall art add to the ambiance.

Apartment in Riverside

4.8 out of 5 average rating, 103 reviews

1BR Near Downtown KC | Free Parking, 2nd Floor

Enjoy a comfortable 1BR in Riverside, just minutes from Downtown Kansas City. This second-floor unit is ideal for solo travelers, couples, or work trips. You’ll have free parking, fast WiFi, easy self check-in, and a fully equipped kitchen for simple meals. Quick highway access makes getting around easy, and the quiet setting offers a relaxed place to unwind after a long day. A practical, well-located home base for short stays or longer visits.

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Superhost

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

4.88 out of 5 average rating, 252 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!

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Guest favorite

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

4.92 out of 5 average rating, 116 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

LocationFamilyCleanliness

Top guest favorite

A well-appointed bedroom features a spacious bed with light-colored linens. Two windows allow natural light to brighten the space. A ceiling fan is overhead, and a small side table holds a decorative item. A plush chair adds to the comfort of the room.

Home in Gladstone

4.98 out of 5 average rating, 127 reviews

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!

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