Family-friendly holiday rentals in Leawood

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!

Family · Indoor spaces · Cleanliness

Bright and spacious townhouse close to everything

Welcome to Overland Park! This spacious townhouse is the perfect home for your family vacation/business trip: Locate in quiet and safe cal-de-sac, yet close to everything! Walking distance to park and Target store; 5 minutes drive to restaurants and shopping as well as grocery stores. Easy access to major freeways. This home is equipped with everything you need: washer/dryer; cooking ware; crib/pac n play available per request. Memory foam mattress. Beautiful private backyard and 2 car garage.

Family · Kitchen · Air conditioning

Spacious 4 BDRM, Game Room, 85” TV, Fenced Yard

Welcome 2025! Weekend Getaway or Business Trip. Stay at our amazing 4 bedroom/3.5 bath home, fully furnished with a mid-century modern vibe. Enjoy the Lower Level featuring an 85" TV, a beautiful wood Stiga ping pong table, and a game table (we even provide poker chips). BBQ grill on the patio. Pets are welcome. Fenced back yard. Fully stocked kitchen. Many extras offered to anticipate a comfortable stay. If you forgot to pack it - we have it! Convenient HWY access. Let us host your next visit!

Kitchen · Indoor spaces · Cleanliness

Spacious Luxury Retreat w/ Hot Tub & Movie Theatre

Relax and take a break in this spacious family retreat! Check out the great outdoor space with 8-person hot tub, firepit and quite patio. Relax inside on the 12' sectional and watch your favorite movie on a 150" screen! Little kids will love swinging on the back yard playset, or climbing on the 25' pirate ship and two-story castle! Pool table in the game room is great for all ages! All bedrooms feature plush bedding and high quality mattresses and smart TVs. Full kitchen cutlery and utensils.

Kitchen · Family · Outdoor spaces

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 · Laundry

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 · Indoor spaces · Amenities

Secluded Oasis within City-kid friendly 4BR Home

Relax and unwind in this cozy updated home with a gorgeous backyard oasis of luscious trees and a serene creek! Sit on the back deck and enjoy the nature that is nestled in this beautiful quiet neighborhood. 4 bedrooms, 2.5 baths, it comfortably sleeps 12! Our home has modern stylish furnishings yet feels cozy to relax, plush beds with luxurious linens, fully equipped kitchen, and play room for endless fun for all ages! A beautifully renovated park is minutes away, including pickleball.

Kitchen · Family · Getting around

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!

Indoor spaces · Kitchen · Walkability

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.

Family · Kitchen · Decor

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!

Indoor spaces · Kitchen · Hospitality

Convenient Overland Park cottage on quiet street

Come relax in this 2 bed/2 bath cottage and enjoy the privacy of an 860 sq foot single family home. Master has queen bed, smart tv and its own private bath. The 2nd bedroom has a queen bed. The couch pulls out to another queen bed for extra sleeping room. Living room has a 50" smart TV. Kitchen has granite counters and is fully stocked to make any great meal. Dining table seats 4 and kitchen seats another 3. Backyard with fire-pit. Pets welcome. Yard is only partially fenced.

Family · Kitchen · Condition

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.

Family · Kitchen · Outdoor spaces