Holiday rentals in Overland Park

A living area features a comfortable brown leather sofa and accent chair, with a wooden coffee table in center. Soft lighting is provided by recessed fixtures, and large windows are dressed with gray curtains. A door leads outside, while artwork adorns the walls.

4.98 out of 5 average rating, 112 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

4.97 out of 5 average rating, 142 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.

Flat in Ward Parkway

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.

4.87 out of 5 average rating, 114 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 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, 516 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.

4.96 out of 5 average rating, 185 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!

4.97 out of 5 average rating, 225 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!

The spacious basement living area features wood-paneled ceilings and soft carpeting. A round dining table with wooden chairs is positioned beside a cozy seating area that includes a couch and an armchair. A TV is mounted on the wall, offering entertainment options.

4.95 out of 5 average rating, 428 reviews

Entire Private Basement with Walkout Entrance

Private basement with two queen beds, couch, memory foam cot or air mattress (upon request), full bathroom, washer/dryer, coffee maker, toaster, microwave, snacks, mini fridge (no freezer), table, WiFi, and a TV (Roku and antenna). We will be upstairs during your stay. We are not loud but you will hear us walk around upstairs. There is a walkout door to backyard. You will be able to park in the driveway. Walkway to gate located on east side of house. Walkway to backyard is well lit.

4.94 out of 5 average rating, 181 reviews

A bright bedroom features a spacious bed covered with a patterned comforter. Natural light enters through a large sliding glass door that opens to a deck, complemented by a decorative window treatment. A small bedside table with a lamp adds to the room's functionality.

Flat in Overland Park

1-bedroom 2nd floor suite w/private entrance!

We feature a smoke- and vape-free home and property. We also have a 2-bedroom listing. Leafy, close-in KS suburb. Apartment on 2nd floor of our home + DECK. Off-street parking for 1 car. Well-lit PRIVATE entrance. Microwave, mini-fridge, coffeemaker, kettle, toaster oven. Coffee, tea; Self-check-in for late arrivals. Very walkable neighborhood just 15 min. from Downtown, KU Med Center, Plaza, galleries, T-Mobile Center. Nearby locally-owned restaurants, coffee shops, parks, IKEA.

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, 167 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, 148 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!

Guest suite in Overland Park

The exterior of the home is framed by lush greenery and colorful flowerbeds. A well-maintained lawn leads to the front entrance, where large windows provide ample natural light. An American flag waves gently from the porch, surrounded by trees offering shade.

4.94 out of 5 average rating, 135 reviews

Private DayLight Basement, Own Entrance, 1800 s/f

Spacious & beautiful 1800 sq ft apartment, sanitized, private entrance w/smart lock, Lg open floor plan, furnished kitchen - appliances, dishes, cookware, own Laundry, bath rm w/2 sinks, 55" smart HDTV, 2 queen beds, one private bedroom, one open bedroom with curtain surround, private lower level of home, Many sunny windows, cul de sac, many restaurants & shops, 2 min to hwy 69, Driveway parking. Pets welcome, Pet rules are under Booking Settings, then House Rules.

4.99 out of 5 average rating, 440 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 roll away (plz req rollaway) Washer/Dryer for your personal use. Fast Wi-Fi Fiber. Sep. fenced off backyard area with Private entry into your basement area that is located around the back of the main house. Parking space on property. Dog park, walking trails. Restaurants close by. Close to highwy, gas stations and shopping. We also have Solar panels that provide some back up for the heat/air and refrig if electricity goes out!!!

Popular amenities for Overland Park holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Overland Park

4.87 out of 5 average rating, 92 reviews

A cozy living room is showcased with two brown leather sofas, a coffee table, and lamps on either side. A television is mounted on the wall opposite the seating. Natural light enters through two windows, while decorative items and plants add a welcoming touch.

Home in Olathe

Newly renovated - all amenities

Guest suite in Kansas City

A cozy bedroom features a spacious bed adorned with decorative pillows and a soft throw blanket. A rustic barn door complements the modern decor. A seating area includes a stylish chair, and a circular mirror reflects the room's calming tones.

4.94 out of 5 average rating, 194 reviews

Modern Farmhouse Suite Newly Remodeled + Amenities

4.98 out of 5 average rating, 60 reviews

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.

Flat in South Lake

Cozy Downtown Apartment

The living room features a comfortable white sofa paired with two wooden chairs. A round coffee table is centered on a patterned rug. A wall-mounted TV sits opposite the seating area, and artwork adorns the walls, complemented by natural light from the windows.

4.89 out of 5 average rating, 79 reviews

*Walk to Downtown OP*/Pet Friendly

Superhost

A spacious balcony is visible, featuring a small table and chairs, ideal for enjoying outdoor meals. The railing provides a clear view of the tree-lined street below, showcasing autumn foliage in vibrant hues, while the skyline can be seen in the distance.

Loft in Volker

4.89 out of 5 average rating, 523 reviews

Private Penthouse +Balcony Overlooking 39th Street

Guest house in Prairie Village

A bright living area features a cozy brown sofa adorned with decorative pillows. A stylish coffee table sits in front, while a modern staircase with black metal railing leads to the lofted bedroom. Large windows provide ample natural light, framed by gray curtains.

4.85 out of 5 average rating, 188 reviews

Prairie Village Modern Farmhouse! Great Location!

Superhost

A cozy living area is illuminated by natural light from multiple windows. Exposed wooden beams enhance the space, while a sectional sofa and a plush armchair provide ample seating. A round coffee table is centrally located, with decorative items arranged thoughtfully on top.

4.83 out of 5 average rating, 29 reviews

3BR Overland Park Home with Patio & Waterfall Pond

The exterior of a midcentury home showcases a modern design with a carport accommodating two vehicles. Mature trees surround the property, providing shade to the landscaped yard. A spacious driveway leads to the entrance, which features a contemporary door and decorative plants.