Holiday rentals in Leawood

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Top-rated holiday rentals in Leawood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A compact kitchen area features dark cabinets and open shelving displaying glassware and appliances. A small dining space is set up with two wooden tables. A ladder leads to the loft bedroom, while a cozy seating area with a neutral sofa is visible in the foreground.
Flat in Ward Parkway
4.97 out of 5 average rating, 142 reviews

Where's Waldo? - Garage Loft

This tiny loft apartment is located in an old neighborhood with big trees, and just a short walk away from Waldo shops, restaurants and bars. Easy travel to Westport, Country Club Plaza, Crossroads, River Market, Power & Light, and many more super fun KC gems. The apartment is in the space that once was our old garage, so it's attached to our home. You have a separate and private entrance, full bath with an amazing shower, a small kitchen with appliances, and a loft bedroom with ladder access.

Top guest favourite
A cozy living area features a brick fireplace flanked by two patterned armchairs and an ottoman. A comfortable sofa with throw pillows faces a television stand. Natural light enters through large windows adorned with light curtains, enhancing the inviting atmosphere of the space.
Home in Overland Park
4.94 out of 5 average rating, 137 reviews

Entire Home, Cozy Retreat Near Kansas City

Come enjoy comfort in a cozy suburban setting. Plenty of room to spread out in this spacious home! It includes 3 beds, 2 full baths, a fully equipped kitchen and formal and informal dining areas. The large living room and outside deck allow for plenty of space to unwind and relax. This home is close to major highways, local shopping areas, and only 20 minutes from downtown Kansas City and Country Club Plaza. It is also universally accessible with wheelchair ramp and an adapted master bathroom.

Top guest favourite
A spacious living area features a large, light-colored sectional sofa positioned on a textured area rug. Exposed wooden beams and modern pendant lights highlight the ceiling. In the background, an open-concept kitchen is partially visible, showcasing a clean, renovated design.
Loft in Kansas City
4.97 out of 5 average rating, 226 reviews

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!

Guest favourite
A spacious bed is paired with two bedside tables, each featuring a lamp on either side. Soft light from the lamps complements the cool green walls, while a decorative pillow adds an inviting touch. Natural light enters through a small window with closed blinds.
Cottage in Kansas City
4.95 out of 5 average rating, 223 reviews

Cozy KC Carriage House

Unique former carriage house. Located in the Waldo neighborhood of Kansas City. Modern, inviting renovation. Charming neighborhood with plenty of amenities and things to do. Great location a short drive to the Country Club Plaza, Arrowhead & Kaufman Stadiums, Power & Light, Crossroads and Downtown. Kansas City Short Term Rental Registration No. NSD-STR-01359. Always ask for the rental registration certificate so your stay isn't cut short with a compliance eviction by city enforcement.

Top guest favourite
A bright bedroom features a spacious bed covered with a patterned comforter. Natural light enters through a large sliding glass door that opens to a deck, complemented by a decorative window treatment. A small bedside table with a lamp adds to the room's functionality.
Flat in Overland Park
4.94 out of 5 average rating, 181 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 favourite
Home in Fairway
5 out of 5 average rating, 100 reviews

Stunning Home W/Game Room + Mins to Plaza

⭐ Fully renovated 3BR home in Fairway, KS — minutes from KC attractions ⭐ Main-level primary suite with spa-style en-suite bath + clawfoot tub ⭐ Open-concept kitchen with quartz counters + full coffee bar ⭐ Cozy living room with gas fireplace + Smart TV ⭐ Upstairs game room with Xbox + lounge space ⭐ Private office, exercise area, and landscaped backyard ⭐Conveniently located less than 5 minutes from The Shops of Prairie Village and roughly 10 minutes from the Country Club Plaza!

Top guest favourite
The exterior of a charming studio guesthouse is presented, featuring a white façade with decorative white trim. Two large windows and a door with a small wreath add to the inviting look. A black vehicle is parked in front, surrounded by greenery.
Guest house in Overland Park
4.99 out of 5 average rating, 168 reviews

Studio Guest House

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

Guest favourite
A bright living area features a cozy brown sofa adorned with decorative pillows. A stylish coffee table sits in front, while a modern staircase with black metal railing leads to the lofted bedroom. Large windows provide ample natural light, framed by gray curtains.
Guest house in Prairie Village
4.85 out of 5 average rating, 188 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.

Top guest favourite
A bright and airy living space features a white sectional sofa and a sleek coffee table. A television is mounted on a wooden shelf, which displays decorative items and books. Light floods in through two windows, highlighting the warm tones of the wooden floor.
Guest house in Kansas City
4.98 out of 5 average rating, 268 reviews

Coho (Cozy Boho) Carriage House, Near Plaza

Come experience this century old, newly renovated carriage house right in the heart of Kansas City! With extremely close proximity to the city’s favorite destinations, this historic abode will help make your stay convenient and cozy. Locations and their distances from where you'll be: - The Nelson-Atkins Museum - 1.6 Miles - The Plaza - 1.7 Miles - Kansas City Zoo - 4 Miles - Union Station - 4.6 Miles - Downtown - 5.1 Miles - Chiefs & Royals Stadiums - 5.6 Miles

Top guest favourite
A cozy sleeping area features a spacious bed with striped bedding and layers of soft blankets. A dark upholstered bench with textured throws sits at the foot of the bed. A bedside lamp provides soft lighting, and a decorative cabinet stands nearby.
Guest suite in Olathe
4.99 out of 5 average rating, 442 reviews

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!!!

Guest favourite
A bright living area features a modern couch adorned with colorful cushions. A small chair and table occupy one corner, and large windows provide natural light, offering views outside. A patterned area rug adds warmth to the space, enhancing the minimalist decor.
Home in Kansas City
4.95 out of 5 average rating, 972 reviews

Minimalist Modern Strawberry Hill Get-Away Home

Entire, separate entry, second floor studio. Minimalist modern decor, nice clean small space with everything you need. We aim to have your stay be an enjoyable experience, greeting you with a clean home, ensuring you have what you need during the stay, and being available as needed. Approximately 5-10 from downtown KCMO, Power and Light, City Market. Within walking distance of a few local family owned restaurants and bars.

Guest favourite
A modern studio suite features a spacious bed with crisp white linens and a cozy reading chair beside it. A kitchenette is visible in the background, equipped with a microwave and mini-fridge. Soft lighting complements the neutral decor, creating a welcoming atmosphere.
Guest suite in Grandview
4.83 out of 5 average rating, 128 reviews

Couples or Solo Travelers - Modern Guest Suite

Guests love the convenience and ease of this modern studio suite w/ separate entrance, privacy gate & parking! Has own heating unit & A/C so you can control the temperature to your liking. This walk-out suite is located on the corner of our house, there's a bedroom above it, so you may hear occasional footsteps, sound generally hasn’t been a problem for any guests that have stayed here.

Popular amenities for Leawood holiday rentals

When is the best time to visit Leawood?

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Avg. price₹5,558₹5,734₹5,910₹6,175₹6,969₹6,440₹5,734₹5,734₹5,381₹5,910₹6,175₹5,822
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Quick stats about holiday rentals in Leawood

  • Total holiday rentals

    Explore 20 holiday rentals in Leawood

  • Nightly prices starting at

    Leawood holiday rentals start at ₹4,411 per night before taxes and fees

  • Verified guest reviews

    Over 2,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Leawood holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Leawood rentals

  • 4.8 Average rating

    Leawood stays are highly rated by guests – averaging 4.8 out of 5!

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