Family-friendly holiday rentals in Prairie Village

The Little House: Cozy Home in Overland Park

- Adorable house on large lot (not a guest house/cottage) - 110 ft Driveway - Sleeping quarters with queen size bed (comfy memory foam mattress) - Living room with 40" smart TV, sofa-sleeper and additional seating - Fully equipped kitchen w/ eating area - Full bathroom w/ clawfoot tub/shower - Sunroom w/ seating area and daybed - Washer/dryer - Office area w/ desk - Deck w/ outdoor seating and grill - 10 min from the Plaza, 15 min from Westport and Downtown, 25 min from the airport - $25 pet fee

Family · Kitchen · Air conditioning

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.

Kitchen · Family · Sleep quality

Stylish 2 Bedroom, 2 Bath Custom Apartment Home

Completely remodeled, stylish apartment home in the heart of downtown Overland Park. Conveniently located 4 blocks from downtown Overland Park's entertainment district with shops & restaurants. Walk across the street to Burg & Barrell for great food or a craft beer. Short walking distance to CVS Pharmacy, Dollar Tree, Metcalf Liquors, China Town & Price Chopper. Centrally located and only 15 minutes from either The Country Club Plaza or Downtown Kansas City. *Apartment is an upstairs unit.

Kitchen · Family · View

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!

Family · Kitchen · Pets

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.

Family · Kitchen · Nearby

Prairie Village Retreat | Fireplace + Game Room

Nestled in the heart of Prairie Village, this delightful home was recently remodeled and is equipped with everything you need for the perfect stay. Enjoy luxury mattresses in the two bedrooms which are both equipped with TVs. Cozy up next to the fireplace with your favorite book or watch a movie on the living room tv. Play a round of foosball or shuffle board with the game on while your favorite dish is smoking in the Traeger outside. Walk to the Shops of Prairie Village within minutes.

Indoor spaces · Kitchen · Condition

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.

Indoor spaces · Family · Checkout

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!

Family · Kitchen · Bathroom

Charming Home in heart of KC

Enjoy midwest hospitality at this charming FAMILY-FRIENDLY home, conveniently located in a beautiful area of KC—3 mi to the Plaza, min away from Prairie Village shops & restaurants, & walking distance to the Fairway Creamery— where you can enjoy breakfast or a sweet treat. See the sites or relax at home with two 75" TVs in a quaint, peaceful neighborhood. NO PARTIES or EVENTS as per Airbnb rules. Walking distance to tennis courts, pool, and parks.

Indoor spaces · Kitchen · Heating

Charming Basement Oasis

Pets- Dogs Only. Private basement suite with walk out entry, situated 1 mile from Historical Downtown Overland District. Within walking distance to South Lake Park. Basement suite is part of a single family home. The house is central air with thermostat located upstairs. Main level is occupied by residents & is separate from the basement suite. Suite includes full kitchen & laundry, full bathroom, walk in closet, one queen bed, & fold down sofa.

Family · Kitchen · Sleep quality

Private Retreat in Walkable Waldo Neighborhood

✔ Free Parking ✔ Laundry Included ✔ 10–15 min to Plaza / Downtown ✔ 20 min to Stadiums ✔ Fast WiFi ✔ Quiet neighborhood Terrific private home in Waldo neighborhood of KC a short drive to the streetcar, Plaza, Stadiums, Power & Light, Crossroads and Downtown as well as Leawood, Prairie Village and Overland Park. Highly rated, highly trusted local Superhosts. No big unreachable property management company or out of town owners here.

Indoor spaces · Family · Pets

Charming Waldo Reader's Retreat

Sweet little bungalow in the heart of Waldo. Sits at the back of the property, so there is no fenced in yard. We had a new driveway poured in 2025, you’re welcome to use that or park on the street. Main bedroom is on the ground floor with an additional bed upstairs (the stairs are ladder-like, so not suitable for everyone!). We love this little house so much and think you will too.

Family · Kitchen · Access