Holiday houses in Overland Park

4.99 out of 5 average rating, 603 reviews

Guesthouse in Westwood

Westwood cottage in garden setting

This 400 sq. ft. guesthouse (studio) on a historic property in Westwood, Kansas has recently been fully renovated and furnished. It has a completely equipped kitchenette, comfortable living area, along with a queen-size bed. The guesthouse also includes a washer/dryer off the kitchen. The guesthouse is a separate dwelling located on a half an acre property which includes the original farmhouse built in 1889 - the guesthouse added in 1920. Westwood, Kansas is 2 miles from the Country Club Plaza.

Townhouse in Overland Park

4.94 out of 5 average rating, 176 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.

5 out of 5 average rating, 110 reviews

Townhouse in Lenexa

Art-filled Retreat w/ King Beds & Private Patio

Unwind at this art-filled, newly renovated townhouse minutes from restaurants, shopping and entertainment. Two king bedrooms with smart TVs make for a great getaway for two couples or a small family. Enjoy the fully-equipped kitchen or grill on the private patio. The basement serves as a lounge and office space and is equipped with a TV, sofa, desk, laundry room and full bath. Walk to the community pool or hit the courts for a game of basketball, tennis, or pickleball with provided equipment.

Superhost

Home in Prairie Village

4.87 out of 5 average rating, 174 reviews

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.

4.94 out of 5 average rating, 487 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.

4.95 out of 5 average rating, 400 reviews

Entire Private Basement with Walkout Entrance

Private basement with two 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 may be able to 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.

4.96 out of 5 average rating, 167 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, 185 reviews

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!

Apartment in Overland Park

4.94 out of 5 average rating, 163 reviews

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 suite in Overland Park

4.94 out of 5 average rating, 124 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.

Guesthouse in Overland Park

4.99 out of 5 average rating, 115 reviews

Studio Guest House

Enjoy Southern OP in this quiet neighborhood. Our studio guesthouse has a full kitchen, a new TV, 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.

4.99 out of 5 average rating, 418 reviews

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!!!

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Other great holiday rentals in Overland Park

4.83 out of 5 average rating, 112 reviews

Private room in Shawnee

Charming King Bedroom in Shawnee

MarkRating, 5 stars4 days ago

Enjoyed my stay very much, I had a little trouble figuring out the lock on the door to get inside but he was nice about that and helped me figure it out.

4.76 out of 5 average rating, 91 reviews

Cottage in Overland Park

Garden Cottage

AmandaRating, 5 stars3 weeks ago

Kelly is welcoming and provides an escape private and serene while being only minutes away from any needs you may have.

5 out of 5 average rating, 16 reviews

Family-Friendly 4BR w/ Game Room, Patio + Firepit

MarloRating, 5 stars1 week ago

Host was very friendly and very responsive. Home was in a beautiful neighborhood, neighbors were very nice as well. Located in a great area. Would highly recommend if your looking for a home near the KC Kansas or Missouri side.

Private room in Overland Park

4.98 out of 5 average rating, 345 reviews

Stay w Superhost Overland Park KS/Kansas City

JacklynRating, 5 stars2 weeks ago

Janet is an amazing host. She made me feel right at home and was very friendly. She even offered me pizza and invited me on the back deck for coffee while she watered her plants. There were so many singing birds out back in the morning and she is located within walking distance to a pond or lake. I didn’t take the time to visit but I’m sure it would be a peaceful experience. Janet is invested in ensuring her guests feel welcome and enjoy the time they spend in her home.

5 out of 5 average rating, 7 reviews

Home in Bucyrus

Modern Oasis-lots of amenities including a pool!

DawnRating, 5 stars6 days ago

This house is amazing! It has all the amenities needed and plenty of space. The house is done with quality finishings and furniture, everything was top notch! The outdoor space is perfect with the pool and covered patio. The doors to outside have tricky locks so be sure to read the house instructions. We only needed the host one time and they responded right away. The neighborhood is quite and makes you feel far from the city even though you are close to restaurants and shopping if wanted. We didn't need that because once we were at the house we didn't want to leave, and can't wait to book again and go back!

Private room in Overland Park

4.94 out of 5 average rating, 441 reviews

Private bedroom, bath, family room .

TammyRating, 5 stars5 days ago

Another great stay!! Michael and Georgie always make me feel at home! I really like the location - close to everything but far enough away to be quiet

Apartment in Overland Park

4.9 out of 5 average rating, 10 reviews

A Cozy Stay in Overland Park!

MikeRating, 5 stars1 month ago

I had a great stay here for 2 weeks. Comfortable place with everything I needed. Dom was quick to communicate with any questions I had. Thanks for the stay!