Family-friendly vacation rentals in Leawood

4.99 out of 5 average rating, 138 reviews

Luxury Retreat 1 block to downtown OP

Looking for better than average? Designed as a comfortable, relaxing, model smart home with the latest features. For the perfectionist that seeks a better stay for work, play or relaxing. Eating healthy? Masticating Juicer, & Ninja. Coffee? French Press, Coffee Grinder, Nespresso, & Keurig. Clean, comfortable, peaceful and one block to downtown Overland Park. Gel, memory foam mattress. Low profile shower w/ handheld. Grout free, clean, Onyx shower. HVAC has UV, Ozone & bio-scrubber. Outdoor pa

An open-concept dining area is furnished with a large wooden table surrounded by six chairs. A modern chandelier hangs overhead, illuminating the space. In the background, a well-equipped kitchen features light grey cabinetry, stainless steel appliances, and a cozy living area with a comfortable sofa.

4.92 out of 5 average rating, 132 reviews

Luxurious & Spacious Ranch 5BR with 2 King Beds

GUEST FAVORITE!! Luxury and spacious ranch home in an unbeatable location near OP Convention Center, the Plaza, and some of the area’s best shopping and dining. Open main level features TWO living spaces, large kitchen, and dining area, giving everyone room to gather and making it perfect for hosting. The incredible basement adds even more fun with a bar, multiple TV's, and game room w/various table & video games for guests to enjoy. This home was made for unforgettable stays and great memories!

4.97 out of 5 average rating, 182 reviews

A compact kitchen area features dark cabinets and open shelving displaying glassware and appliances. A small dining space is set up with two wooden tables. A ladder leads to the loft bedroom, while a cozy seating area with a neutral sofa is visible in the foreground.

Apartment in Waldo

Where's Waldo? - Garage Loft

This tiny loft apartment is located in an old neighborhood with big trees, and just a short walk away from Waldo shops, restaurants and bars. Easy travel to Westport, Country Club Plaza, Crossroads, River Market, Power & Light, and many more super fun KC gems. The apartment is in the space that once was our old garage, so it's attached to our home. You have a separate and private entrance, full bath with an amazing shower, a small kitchen with appliances, and a loft bedroom with ladder access.

Townhouse in Shawnee Mission

4.95 out of 5 average rating, 102 reviews

Look Here Fly w Me! 1K/ 3Q+F~ReclinerConv Ctr

6 min to Overland Park Convention Center, just mins to I-435. Enjoy this location central to everything KC! 1 K, 3 Queens, 1 Full. Newly remodeled, Kitchen is set up for your cooking needs, Coffee Bar, Keurig or traditional coffee. Have some fun w the Foosball table or BBQ on the Patio/Deck. 2 Full Bathrooms, Shower or tub, plenty of room to spread out, 5 Smart TVs, fast internet. **Starting Sept 15 2026 pricing looks different. Hosts are absorbing platform fees now. Guests just pay taxes**

Guesthouse in Kansas City

The exterior of the pool house features large glass windows that enhance natural light, showcasing a blend of modern architecture and a heated pool. A patio area is visible, with lounge furniture positioned beside the pool and artificial turf complementing the outdoor space.

4.86 out of 5 average rating, 223 reviews

The Black Walnut KC Pool House & Hot Tub

Beautiful pool house that sleeps up to 5 with two amazing king size beds, a queen pull out couch, and twin bed along with a beautiful full bathroom, kitchenette, laundry, and bar! Custom artificial turf, heated pool, and hot tub that are open year round make this a unique resort style stay in the heart of the favorite neighborhood of all of Kansas City - Brookside! We do not do parties or events, but love your furry family! @theblackwalnutkc Perfect for couples, families or friendscations!

A dining area is featured with a wooden table surrounded by four chairs. A colorful piece of wall art adds interest to the room. Opposite, a wooden sideboard displays dinnerware, while an open doorway leads to a comfortable living area with a sofa.

4.97 out of 5 average rating, 246 reviews

Glenwood Getaway - Great Location!

Experience the best of Overland Park from our charming, updated ranch. Nestled in a quiet neighborhood near downtown, this home allows you to experience the local lifestyle at its best. With two bedrooms, a modern bathroom and all the comforts of home, you will never want to leave! The interior blends cozy charm with contemporary amenities, while the secluded half-acre backyard is perfect for unwinding. Whether you’re here for a weekend escape or a longer stay, your perfect getaway awaits!

Apartment in Shawnee Mission

A cozy bedroom features a spacious bed adorned with a patterned quilt and decorative pillows. Bedside tables are positioned on either side, and natural light filters in through two windows, complemented by navy curtains. A plush rug adds comfort to the wooden floor.

4.99 out of 5 average rating, 116 reviews

Cozy Downtown Apartment

Be our guest and enjoy a pleasant and peaceful retreat in your private, tastefully decorated apartment attached to our home. The open design features a spacious living room, ROKU TV, a desk and full-scale kitchen. Drift off into a deep sleep in the separate bedroom in the luxurious and cozy queen size bed. The large, illuminated bathroom offers a tub with pulsating jets as well as a separate shower, floating vanity and laundry closet. Downtown shops and dining are just a short walk away.

4.95 out of 5 average rating, 282 reviews

A spacious living area features a large, light-colored sectional sofa positioned on a textured area rug. Exposed wooden beams and modern pendant lights highlight the ceiling. In the background, an open-concept kitchen is partially visible, showcasing a clean, renovated design.

Loft in Kansas City

Truman Loft

Truly one of a kind Historic property converted into a spacious, cozy loft in the heart of South KC. This 100-year-old space(5 min from HS Truman farm. He spoke on this stage on his first political campaign) has been completely rennovated with concrete countertops, beautifully vaulted ceilings, huge bathroom, built in workspace and even a fun kid's room. Let the natural light pour through the massive windows or close the curtains and dim the lights:) We hope you enjoy it as much as us!

A serene bedroom space is presented with soft, neutral tones. A spacious bed is dressed with white linens, accompanied by decorative pillows. Natural light filters through sheer curtains, with a floral pendant light hanging above. A cozy blanket is casually draped over the bed.

4.95 out of 5 average rating, 154 reviews

modern x charming 1930s farmhouse! 10 min plaza!

Step into our fully renovated 1930s farmhouse and be welcomed by natural light and an inviting open concept. The kitchen features beautiful marble countertops and all the essentials. Relax in the stunning black freestanding bathtub or dine al fresco on the spacious outdoor patio. With three cozy bedrooms, including two queen-size beds and one full-size bed, this home can accommodate up to six guests. Experience the perfect blend of old-world charm and modern convenience during your stay.

A private pool surrounded by a diamond cut concrete patio is visible. Lounge chairs and an umbrella provide shaded seating. The backyard is enclosed by a privacy fence, with the house in the background featuring multiple windows and a deck access.

4.96 out of 5 average rating, 167 reviews

Private Pool Oasis | Family Escape • 4BR Sleeps 10

Family oasis -4-bedroom home with heated private pool, ideal for families and professionals. Comfortably sleeps up to 10 guests and is a great home base for out-of-town visitors attending World Cup matches or watching the games during downtime. Located in a desirable neighborhood close to dining, shopping, and golf. Features 4 bedrooms (2 en suite), 3.5 baths, a fully equipped kitchen, large laundry room, and two living spaces. Pool open April–late Sept/early Oct, weather permitting.

4.99 out of 5 average rating, 133 reviews

Prestige-Stunning Home W/Game Room+ Mins to Plaza

⭐ Fully renovated 3BR home in Fairway, KS — minutes from KC attractions ⭐ Main-level primary suite with spa-style en-suite bath + clawfoot tub ⭐ Open-concept kitchen with quartz counters + full coffee bar ⭐ Cozy living room with gas fireplace + Smart TV ⭐ Upstairs game room with Xbox + lounge space ⭐ Private office, exercise area, and landscaped backyard ⭐Conveniently located less than 5 minutes from The Shops of Prairie Village and roughly 10 minutes from the Country Club Plaza!