Holiday houses in Leawood

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.

4.97 out of 5 average rating, 127 reviews

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, 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.

4.92 out of 5 average rating, 143 reviews

Luxurious * 4BD 3.5BA * Spacious * Game Room * Big Yard

1st Floor: Master Bedroom-King Bed, Master Bath with Jetted Tub, separate shower, 75" TV. Kitchen is large with a breakfast bar, dining table with 58" TV, half bath and laundry off of the kitchen. Living Room has 82" TV plus a large formal dining table. 2nd Floor: Bedrooms 2,3, & 4 with Queen Beds. Loft has a Queen Pullout Couch. BR 2&3 Share a bathroom. BR 4 has private bath. TVS in every room. Loft has office space with TV/'laptop monitor, office space, and black and white laser printer.

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.

4.96 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!

4.99 out of 5 average rating, 108 reviews

Home in Prairie Village

modern x charming 1930s farmhouse! 10 min plaza!

Step into our fully renovated 1930s farmhouse and be welcomed by natural light and an inviting open concept. The kitchen features beautiful marble countertops and all the essentials. Relax in the stunning black freestanding bathtub or dine al fresco on the spacious outdoor patio. With three cozy bedrooms, including two queen-size beds and one full-size bed, this home can accommodate up to six guests. Experience the perfect blend of old-world charm and modern convenience during your stay.

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.

Superhost

Apartment in Grandview

4.75 out of 5 average rating, 146 reviews

The Resting Place, Grandview Home-Lower

This listing is for a basement apartment only in a single family residence home. (Upper level of home may have other guests.) This space is in lower level of home, completely separate from the upper level of home with it’s own private, secure entrance. Ethan Allen custom swivel chairs, 55 inch Panasonic Plasma TV, Eddie Bauer Home King-Size Bed with Luxury 15 " Pillow top mattress. Full size, equipped, kitchen w/ all the essentials.*Please review house rules prior to booking

Guesthouse in Prairie Village

4.85 out of 5 average rating, 167 reviews

Prairie Village Modern Farmhouse! Great Location!

Enjoy your home away from home with style! This separate guest house has 1 bedroom & 1 bathroom that gives you privacy while still being centrally located in Prairie Village of Kansas City. Floor to ceiling shiplap walls, wood floors, black metal railing, & stylish decor you will feel like you're in an episode of Chip and Joanna Gaines' Fixer Upper! The home has its own private entrance, Washer/Dryer in unit and a fully functioning kitchen. High speed GooglFiber internet.

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Other great holiday rentals in Leawood

Apartment in Overland Park

4.97 out of 5 average rating, 36 reviews

Cozy Downtown Apartment

NatalieRating, 5 stars4 days ago

We have stayed in many AirB&Bs and this home in Overland Park is the best one we’ve stayed in! It was squeaky clean, had quality craftsmanship, tastefully decorated, well stocked with anything you may need, a comfortable bed, and the perfect location! I appreciate that Cheryl and Steve warmly greeted us upon arrival, and were available next door if we needed them. However, they also gave us plenty of privacy. We didn’t cook, but there was a full kitchen we could use if we stayed longer. We appreciated the washer and dryer and closet to hang up clothing as well as the comfortable sleeping cots for our two young kids. The huge Farmers Market was temporary relocated behind the AirBnB, which made a perfect place to get breakfast on Saturday morning. Down the street there was a playground and a park, which would be nice place to go with littles. They also have a swing set in their yard, which was nice for our kids to get the wiggles out before we hit the road. We will return for sure!

5 out of 5 average rating, 55 reviews

Home in Olathe

Amazing Full Basement Apartment

CaroleAnneRating, 5 stars1 day ago

Great stay very well appointed and so comfortable everything you need and just a beautiful stay

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, 20 reviews

Home in Lenexa

Luxury in Lenexa w/heated pool

MeredithRating, 5 stars3 days ago

I really enjoyed our time in Lenexa! This house was in the perfect location and was clean and spacious!! My dogs enjoyed the backyard, and the pool was amazing for the hot days! Thank you again for sharing this amazing property!

4.9 out of 5 average rating, 41 reviews

Guest suite in Grandview

Cozy Chic Basement!

DodjiviRating, 5 stars1 day ago

Chad & Christina are one phenomenal hosting couple. They made me feel right at home, responsive and flexible. That bed was a bomb with the memory foam soothing my body. The cleanliness was on point. Your kids are adorable! Thanks guys, and I sure will be back again when I'm in town.

5 out of 5 average rating, 66 reviews

Apartment in Kansas City

Forest Retreat in the City!

TrishRating, 5 stars3 days ago

This place is amazing. It’s tucked back in a residential neighborhood in Red Bridge, with a long driveway that goes back to a little paradise with huge old trees. You feel like you’re back in the forest, even though it’s in the city. The space was perfect, kitchen was well equipped, wonderful bathroom, and we enjoyed hanging out in the nice living room. Though we didn’t use the back patio, we did lie in bed at night and watch the fireflies and the bunnies outside the sliding glass doors. And… it is walking distance to the Red Bridge shopping center with a nice grocery and a coffee shop. Wonderful!!! We were there for a family reunion weekend and this place was perfect for that.