Holiday houses in Leawood

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.

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.

Apartment in Overland Park

4.99 out of 5 average rating, 73 reviews

Upscale, English Basement Garden Apartment

Upscale!! You will be wowed by this beautiful English daylight basement apartment located in our Leawood mansion. With our long experience as Super Hosts you can trust us to bring you beauty, comfort and well designed space. Money well spent. We've thought of almost everything to make your stay the very best possible. Located in a safe upscale neighborhood, with direct access to I-435. Great restaurants, shopping, theaters, 20 minutes to the Plaza, hockey, baseball, and of course the CHIEFS!

4.96 out of 5 average rating, 165 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, 184 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, 107 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.

4.91 out of 5 average rating, 114 reviews

Home in Prairie Village

Charming, Stylish 3-bdrm house - Central location

Feel at home in this charming house on a quiet street. Styled with all new modern furnishings! Beautiful bay window in living room looks out onto a mature tree lined street. Take a family walk with the kids to the park down the street or take the dogs on a stroll through the peaceful neighborhood. Drink coffee or wine by the electric fireplace that makes the living room extra cozy during these winter months. 55" LG Roku Smart TV - log in to your favorite streaming services.

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.

Holiday home in South Lake

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!

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.

5 out of 5 average rating, 19 reviews

Home in Nall Hills

Stunningly Remodeled Ranch w/ King Bd-Fire pit

Enjoy a stylish experience while you relax and unwind at this centrally-located home. Recently updated, this home has everything you need with 3 bedrooms and 2 baths and minutes away from everything. Our home has modern stylish furnishings, plush beds, fully equipped kitchen, full laundry, and 1Gb Wi-Fi for work or streaming needs. The basement has ping pong and there is a fenced yard for pets and kids to play. Perfect for all ages!

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Popular amenities for Leawood holiday rentals

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Other great holiday rentals in Leawood

4.83 out of 5 average rating, 112 reviews

Private room in Shawnee

Charming King Bedroom in Shawnee

IsaiahRating, 5 stars2 days ago

Great stay as always

5 out of 5 average rating, 6 reviews

EasyBlooms Cottage | Cozy, Eco-Friendly Retreat

MichaelRating, 5 stars1 day ago

Donna was a great hostess and very responsive. I really appreciated that. I will be looking for her property’s availability next time, when I make plans to visit my hometown of Kansas City!

Apartment in Kansas City

4.83 out of 5 average rating, 54 reviews

Peaceful, Waldo Apartment

BrianRating, 5 stars4 weeks ago

Had a great stay! Very clean and comfortable accommodations. Jacob gave helpful instructions on getting inside prior to my arrival. Very nice setup and plenty of space. The shower had great water pressure. Coffee was available for mornings. Easy to get to events in KC, but located in a quiet area. Would stay again!

4.71 out of 5 average rating, 391 reviews

Heated All season pool Private Spacious King bed

DarlishaRating, 5 stars2 weeks ago

I had last min plans to get my family and friends together Boris responded immediately after booking and the place was very nice and spacious more then enough space and the pool was perfect for the kiddos will book again

Private room in Overland Park

4.94 out of 5 average rating, 438 reviews

Private bedroom, bath, family room .

KalynRating, 5 stars2 weeks ago

Great place to stay. My husband and I stayed for 3 nights in May. We enjoyed the privacy Michael's place provided. We had the whole finished basement to ourselves which included a family room and a bedroom with an attached bathroom.

5 out of 5 average rating, 13 reviews

5BR w Master on Main, Game Rm, Firepit, Playground

JakeRating, 5 stars2 weeks ago

We enjoyed our stay at this house near Kansas City! The location was a quick drive away from lots of restaurants. We enjoyed spending time with family who live nearby and attractions for our 4 kids (Zoo & aquarium, Wonderscope, Kids Empire, Kaleidoscope, Science City, etc). The house was very well stocked with everything we needed for a comfortable stay for both adults and children. We appreciated the updated design & decor. The kids loved the arcade and games in the basement as well as the playground outside. The fire pit worked very well. We were pleasantly surprised that the deck’s pergola was also covered with a mostly waterproof clear covering to help protect from the rain. We would definitely stay here again!