Family-friendly holiday rentals in Overland Park

Stylish 1 bedroom, 1 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 many unique shops & restaurants. Walk across the street to Burg & Barrell for great food or a craft beer. Short walking distance to CVS Pharmacy, Hawaiian Bros, Dollar Tree, Metcalf Liquors & Price Chopper. Centrally located and only 15 minutes from The Country Club Plaza or Downtown Kansas City. *This is an upstairs unit.

Family · Indoor spaces · Walkability

Overland Park Home - Stay Close to Everything

3 King Size Beds, 1 Bunk Bed (Full & Twin Size) 6 Smart TVs, Driveway Parking, Washer & Dryer, oversized backyard w/ patio, batting cage & swing set. *15 Minutes to Downtown KC, Country Club Plaza, Crown Center! *23 Min to Chiefs & Royals stadiums. *5 Minutes to Downtown Overland Park ft. restaurants, farmers market, bars & more! Main Level: + Open living room + Updated kitchen & dining + 3 bedrooms & full bath Lower Level: + Second living area + 1 bedroom & full bath + Wet bar + mini fridge

Kitchen · Family · Quiet

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!

Kitchen · Family · Decor

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.

Indoor spaces · Family · Condition

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!

Kitchen · Family · Accuracy

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 · Kitchen · Hospitality

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!

Kitchen · Indoor spaces · Sleep quality

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.

Kitchen · Family · Laundry

Studio Guest House

Enjoy Southern OP in this quiet neighborhood. Our studio guesthouse, completely separated from the main house, has a full kitchen, TV, a new a/c/heater, and google fiber internet. In case you get lonely, we have 2 friendly dogs always looking for attention. We are about 45 minutes away from the Kansas City airport, Kauffman Stadium, Arrowhead Stadium, the KU main campus. We are 10-15 minutes from the Scheels soccer complex. Overland Park has plenty of Kansas bbq and shopping.

Kitchen · Family · Value

Chic Modern Home in Downtown Overland Park

Chic modern stay in the heart of Downtown Overland Park! Relax with a plush king and queen bed, 1Gbps fast Wi-Fi, & washer/dryer. Walk to cafes, bars, shops, & the farmer’s market. Just 15 min to Plaza/downtown KC, 25 min to Arrowhead/MCI airport. Fully equipped kitchen & parking included. Perfect for couples or small groups (sleeps 4 w/ a queen air mattress available upon request). Book now for a comfy, convenient getaway that blends style & location—your ideal home base!

Family · Indoor spaces · Grill

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 · Parking

Pink Spot w/ Hot Tub, Game Room + Crazy Bunk Bed!

❤️ Welcome to this one-of-a-kind three-bedroom home nestled in a peaceful and secure neighborhood just off I-35. With a range of unique amenities, it’s the ideal place for you and your group or family to relax, unwind, and create unforgettable memories together. Hot Tub, Mini Golf, Bowling, Game Room, Bunk Bed with Slide, Fire Pit, Arcades, Pool Table, Shuffleboard, Board Games and many more - you'll never want to leave! ❤️

Indoor spaces · Kitchen · Hospitality