Holiday houses in Overland Park

4.99 out of 5 average rating, 602 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, 175 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.

4.97 out of 5 average rating, 126 reviews

Home in Overland Park

South OP, 4 Bedroom, Game Room, 85” TV

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!

5 out of 5 average rating, 109 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.

4.87 out of 5 average rating, 173 reviews

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.

4.94 out of 5 average rating, 486 reviews

Home in Overland Park

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.

4.96 out of 5 average rating, 163 reviews

Home in Overland Park

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, 182 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!

4.94 out of 5 average rating, 162 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.

Holiday home in Overland Park

4.93 out of 5 average rating, 138 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!

Apartment in Downtown Kansas City

4.9 out of 5 average rating, 108 reviews

KC Apt River Market-403

Clean and convenient 1 bedroom apartment. 20 minutes from the Airport. Located in the vibrant, creative and diverse River Market community with access to many attractions and entertainment areas of Kansas City. Take the free streetcar to Union Station, Crossroads, Power & Light District/T-Mobile Center, Convention Center and more. Your stay includes pool and fitness center access, as well as a community rooftop courtyard with skyline views. Close the KC Current soccer.

Guesthouse in Overland Park

4.99 out of 5 average rating, 113 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.

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Other great holiday rentals in Overland Park

Guest suite in Merriam

4.82 out of 5 average rating, 304 reviews

The Den - Near Downtown KC

AlexandraRating, 5 stars3 weeks ago

Very spacious living room and bathroom. Simple furnishings, but has the things you need. It is a downstairs unit, so there is some noise from upstairs tenants but there’s a fan and space heater provided in the bedroom that are good white noise for sleeping.

4.86 out of 5 average rating, 98 reviews

Stylish 1 bedroom, 1 bath custom apartment home

RobertRating, 5 stars1 week ago

Great location in Overland Park! Private entrance and parking, easy check in and out. Perfect for a quick KC trip, you will need a car!

4.97 out of 5 average rating, 34 reviews

Cozy Downtown Apartment

EricRating, 5 stars5 days ago

My wife and I had a great stay at Cheryl's guest suite! From a dedicated parking spot, to easy access, to a fully stocked and immaculate space, I would 100% recommend staying here. The location can't get any better - 18 mins to downtown, 30 mins to airport, walking distance to old OP. Cheryl is an excellent communicator, and was so friendly and accommodating for us on check in / check out.

4.87 out of 5 average rating, 23 reviews

Tiny home in Bucyrus

Kevin's Cabin

KarenRating, 5 stars5 months ago

We loved staying in this enchanting cabin. The cabin is so modern yet quaint and cozy. The entire wall of windows opens up to an outside view. Including a stream and bridge. The morning views were peaceful and the evening views were lit up with lights hanging from the trees. Everyone we met were so nice and helpful with anything we needed. We truly couldn't have asked for more.

5 out of 5 average rating, 19 reviews

Home in Lenexa

Luxury in Lenexa w/heated pool

TediRating, 5 stars2 weeks ago

We loved this house! It was the perfect weekend getaway for our crew. We really enjoyed the hot tub and pool. It provided ample space and had all the details you could want, plus more. We hope to be back!