Family-friendly holiday rentals in Overland Park

Townhouse in Overland Park

A welcoming living room features a high ceiling with a large clock above the white brick fireplace. A comfortable sofa and plaid armchair are complemented by wooden coffee and side tables. Soft lighting is provided by two lamps, creating a relaxed ambiance.

4.94 out of 5 average rating, 210 reviews

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.

4.93 out of 5 average rating, 392 reviews

A spacious sleeping area features a queen-size bed dressed in soft linens and a blue sofa, along with a coffee table. A smart TV is mounted on the wall, and a desk is positioned in the adjacent office area, illuminated by natural light from nearby windows.

Home in Mission

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

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, 153 reviews

Private Pool Retreat/Stylish 4BR Getaway/Top Rated

World Cup–ready 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 early April–late Sept/early Oct, weather permitting.

A cozy seating area is arranged with two leather armchairs and a spacious sectional sofa. Three wooden side tables sit on a soft area rug, accentuating the space's comfort. Natural light filters through a nearby window, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 147 reviews

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!

4.88 out of 5 average rating, 124 reviews

A cozy living area showcases a comfortable armchair and a stylish ottoman atop a patterned rug. A modern kitchen with gray cabinetry and marble accents is visible in the background, enhancing the open layout. Natural light brightens the space through adjacent windows.

Flat 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.

A bright living room features a comfortable leather sectional couch and two circular coffee tables. Natural light floods in through large windows adorned with dark curtains. Exposed wooden beams add character to the ceiling, while a modern TV is mounted on the wall.

4.94 out of 5 average rating, 162 reviews

Room to Spread Out • Central Overland Park

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

4.88 out of 5 average rating, 210 reviews

A spacious entertainment area is highlighted by a large projection screen showcasing vibrant content. Modern wall sconces provide soft illumination, while a sleek glass table complements the contemporary sectional seating arranged thoughtfully to encourage relaxation.

Home in Prairie Village

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.

4.98 out of 5 average rating, 504 reviews

A cozy sleeping area features a spacious bed with striped bedding and layers of soft blankets. A dark upholstered bench with textured throws sits at the foot of the bed. A bedside lamp provides soft lighting, and a decorative cabinet stands nearby.

Guest suite in Olathe

Secret Garden Short Stay

1 King Bed. 1 Twin air mattress rollaway (plz req rollaway) Washer/Dryer for your use. Wi-Fi Fiber. Sep. fenced backyard area with Priv. entry into your basemnt area that is located around the back of our main house. Parking space on prop. Dog park, walking trails. Pet fee is charged. Close to highwy, & shopping. We also have Solar panels that provide some back up for the heat/air and refrig. Entire daylight basement is separate from us upstairs with locked door. Does have couple of steps.

A cozy living area is highlighted by a large wall mural featuring trees and soft light. A sectional sofa and an armchair provide comfortable seating. A small coffee table sits on a patterned area rug, while a television and a work desk are positioned nearby.

4.94 out of 5 average rating, 543 reviews

Convenient Overland Park cottage on quiet street

Come relax in this 2 bed/2 bath cottage and enjoy the privacy of an 800 sq foot single family home. Master has queen bed and it's own private bath. 2nd bedroom has a queen bed. A queen size aerobed mattress is provided for extra sleeping room. Has a 50" flat screen TV equipped with Netflix/DVD player. 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.

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, 220 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!

Guest house in Overland Park

The exterior of a charming studio guesthouse is presented, featuring a white façade with decorative white trim. Two large windows and a door with a small wreath add to the inviting look. A black vehicle is parked in front, surrounded by greenery.

4.99 out of 5 average rating, 216 reviews

Studio Guest House

Enjoy Southern OP in this quiet neighborhood. Our studio guesthouse 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, and the Harry S Truman sports complex. We are 10-15 minutes from the Scheels soccer complex. Overland Park has plenty of Kansas barbecue and shopping.

Holiday home in South Lake

A living area features a plush blue couch adorned with decorative pillows, complemented by a clear glass coffee table. A cozy chair with a light throw blanket sits nearby. Bright natural light filters through sheer curtains, enhancing the room's inviting ambiance.

4.91 out of 5 average rating, 158 reviews

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!

Popular amenities for Overland Park family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 171 reviews

A spacious dining area features a large oval wooden table surrounded by black chairs. A modern light fixture hangs above, providing illumination. An open view into the kitchen shows white cabinetry and stainless steel appliances, enhancing the airy feel of the room.

Home in Volker

Westport Manor | Hot Tub & Speakeasy!

Home in Downtown Kansas City

A serene outdoor space is showcased with a heated saltwater pool surrounded by smooth concrete and lush greenery. Two lounge chairs are positioned near the pool, while a cozy structure is visible in an adjacent area, offering a shaded retreat.

4.83 out of 5 average rating, 179 reviews

Amazing House with Heated Pool & Rooftop Hot Tub!

Apartment in Southmoreland

The bedroom features a cozy queen bed with high-quality linens, adorned with a bright yellow throw and colorful decorative pillows. Natural light filters through two large windows, enhancing the space. Wall art represents Kansas City, complementing the neutral color scheme.

4.83 out of 5 average rating, 334 reviews

The Nelson & Plaza Condo w/ free parking!

4.93 out of 5 average rating, 196 reviews

A spacious living room features a gray-brick fireplace with an artistic representation of a tree above. Light gray walls complement the subtle decor, while plants and decorative items are arranged on white bookshelves. A brown couch with blue cushions faces a glass table, enhancing the inviting space.

Home in Shawnee

5 level home. Holiday Ready.

4.86 out of 5 average rating, 125 reviews

A spacious backyard reveals a hot tub surrounded by brick pavers, with a relaxing hammock nearby. The house displays a second-floor balcony overlooking the well-maintained lawn, illuminated by soft string lights. A patio area is visible, ideal for outdoor gatherings.

Home in Southmoreland

6BR KC Cozy Family Home w/HotTub Theater & Gym

A cozy living area includes a sectional sofa and accent chairs arranged around a circular coffee table. Natural light filters through sheer curtains, and a mirror reflects the relaxed setting. Beamed ceilings add a touch of character to the modern decor.

4.94 out of 5 average rating, 171 reviews

NEW! Updated *|* Stylish *|* OP getaway w/ Hot Tub

Guest house in Independence

A serene natural setting features a gently flowing spring-fed creek cascading over stones. Lush greenery surrounds the area, with small plants positioned along the water's edge. A wooden footbridge crosses the creek, enhancing the tranquil outdoor atmosphere.

4.9 out of 5 average rating, 169 reviews

Adorable one bedroom Guesthouse in the woods.

5 out of 5 average rating, 110 reviews

Home in Prairie Village

Sleeps 12! w/King Beds+Hottub+Gym+Theater

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 154 reviews

A cozy living area showcases a sectional sofa and a matching ottoman on a patterned area rug. Natural light enters through large, partially shaded windows, enhancing the space. A flat-screen TV is positioned on a media console, providing entertainment options.

Home in Merriam

~Antioch Cozy Ranch~Pet Friendly~Central~Remodeled

4.82 out of 5 average rating, 164 reviews

A spacious interior features a high ceiling with exposed beams, enhanced by large windows allowing natural light. A dining area with several chairs surrounds a central table, while a sleek kitchen bar with stools is visible. Additional storage spaces are integrated along the wall.

Home in Shawnee

Royal Rabbit Charming Bungalow

4.8 out of 5 average rating, 161 reviews

A modern kitchen showcases green cabinetry complemented by a herringbone backsplash. A round wooden dining table with a bowl of apples is positioned in the foreground, and black appliances create a sleek contrast. Natural light enters through a nearby window, illuminating the space.

Home in Mission

KC Urban Oasis w/ 8Ft Fence & Unique Kitchen

4.98 out of 5 average rating, 245 reviews

A modern living area features a stylish light-colored sofa and a green accent chair, arranged around a circular coffee table. Floor-to-ceiling windows provide ample natural light and views of the surrounding greenery. A wooden accent wall and sleek television add to the contemporary design.

Home in Rosedale

Luxury 2bd+Loft Sleep 7 <20 min from World Cup

4.99 out of 5 average rating, 105 reviews

A dining area is highlighted by a round wooden table surrounded by four gray chairs. Floating shelves are adorned with books and decorative items. A large potted plant adds a touch of greenery, while a decorative mirror reflects light and space.

Home in Southmoreland

Coveted Museum District Stylish Eastlake Victorian

4.98 out of 5 average rating, 248 reviews

A welcoming living room features a large gray sectional sofa and an additional armchair, providing comfortable seating for up to five guests. A wooden coffee table sits in front, while natural light streams through the windows. A Smart TV is mounted on the wall for entertainment.

Home in Waldo

*The Green House* King bed✩Outdoor Hangout✩Netflix

A bright and inviting living area showcases a modern red sofa with decorative cushions. Colorful artwork adorns the walls, and a warm wooden floor adds character. Natural light filters in through large windows, enhancing the cozy atmosphere of the space.

4.92 out of 5 average rating, 330 reviews

Comfortable home~quiet neighborhood

4.96 out of 5 average rating, 104 reviews

A welcoming two-story home is surrounded by a manicured lawn, featuring vibrant flower beds. Rocking chairs are positioned on a large front porch with hanging planters. The sun casts gentle shadows across the neatly trimmed grass, enhancing the peaceful outdoor setting.

Home in Cleveland

Meadow Brooke Lane

Family-friendly home rentals with a pool

4.82 out of 5 average rating, 55 reviews

A stylish living area features a plush teal sofa with decorative pillows, paired with a dark coffee table. A flat-screen TV is mounted on the wall opposite, and modern kitchen appliances are visible in the background, surrounded by sleek cabinetry. A light rug adds warmth to the wooden floor.

Flat in Overland Park

Cozy KC Retreat with Hot Tub | Near Power & Light

4.96 out of 5 average rating, 410 reviews

Bungalow in Kansas City

Tiki Lounge • Sauna • Pool • Designer KC Bungalow

4.97 out of 5 average rating, 218 reviews

The living room features a warm, inviting color scheme with a seating arrangement that includes a spacious brown sofa, an armchair, and an ottoman. A television is mounted above a modern gas fireplace, complementing the cozy ambiance. Natural light filters in from a nearby window.

Flat in Lee's Summit

Cozy apartment, private entrance, gas fireplace

4.93 out of 5 average rating, 44 reviews

A modern tiny home is nestled among lush greenery, featuring a large deck with seating. Glass doors open to the deck, offering views of a gentle stream. A stone path leads over a small bridge, connecting the home to the natural surroundings.

Tiny home in Bucyrus

The Cabin

4.85 out of 5 average rating, 142 reviews

The spacious bedroom features a queen bed with a decorative comforter and a plush area rug. A ceiling fan hangs above, and natural light flows through partially draped windows. Additional furnishings include a dark armchair, a small ottoman, and a bedside table with a framed art piece.

Villa in Kansas City

The Nest Villa with Pool in Kansas City

4.97 out of 5 average rating, 138 reviews

A single-story bungalow is surrounded by lush green grass and large shade trees. The light-colored exterior features a bold blue front door, and multiple windows showcase views of the well-maintained yard. A paved driveway leads to an adjoining garage.

Home in Lee's Summit

Cozy home, work/play, easy access to all things KC

5 out of 5 average rating, 244 reviews

An aerial view reveals a shared outdoor pool surrounded by a concrete patio, adorned with lounge chairs and shaded areas. A charming guesthouse is visible nearby, complemented by a flagpole featuring an American flag, all set within a spacious green landscape.

Guest house in Shawnee

1 of a Kind Guesthouse on 4 Acres. Dogs allowed