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, 109 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

5 out of 5 average rating, 6 reviews

EasyBlooms Cottage | Cozy, Eco-Friendly Retreat

MichaelRating, 5 stars6 days 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 Overland Park

4.85 out of 5 average rating, 74 reviews

LightRoom-Sleek stylish space w/ private workspace

AbigailRating, 5 stars2 weeks ago

This space was the ultimate in convenience! Location couldn't be better; it's right off the freeway, and down the street (walking distance) there's a park with a walking/biking trail, and a wonderful local coffee shop/cafe. You'll get one covered parking spot right in front of the door for easy loading and unloading of luggage. Fully stocked kitchen was perfect for making dinner at the end of the day, coffee supplies included. The space is modern, tidy, and streamlined, with plenty of silk plants for a touch of nature. The bed was on the firm side with super comfy pillows and bedspread. Ana was very proactive with communication throughout the process (including making sure I was aware there is no washer/dryer in the unit, which wasn't a problem for me). Highly recommend Ana's place for convenience, ease, and relaxation!

Home in Grandview

5 out of 5 average rating, 4 reviews

Italian Inspired Home

PaulRating, 5 stars3 months ago

The home was very clean. There is not a television or a microwave. Neither of which were an issue for our stay. The lighting in the unit is limited with only one good lamp for reading.

5 out of 5 average rating, 356 reviews

Private room in Mission

Guest Suite: Your Home Away from Home

KristineRating, 5 stars2 weeks ago

Don and Chris were so incredibly welcoming! I immediately felt comfortable, which doesn’t sound like a lot but it was my first time staying at an Airbnb alone so it was important to me that I felt safe. Don gave me a thorough tour and the space is even better than described! They even provided so many extra amenities and drinks and snacks, which I of course don’t expect, but am very grateful for! They also helped me treat my allergies, and I couldn’t be more appreciative!! They will literally go above and beyond to make you feel at home and truly enjoy your trip. Bonus: their dogs (Casper and Cooper) are the cutest/sweetest! I’m already missing them🥺 will definitely return. 100% book if their space is available!

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!

5 out of 5 average rating, 13 reviews

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

JakeRating, 5 stars3 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!