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 spacious sleeping area features a queen-size bed dressed in a turquoise coverlet, complemented by decorative pillows. Natural light floods through a nearby window covered with light curtains. A wooden dresser and bedside table add warmth to the room, while framed artwork enhances the decor.
Guest house in Westwood
4.99 out of 5 average rating, 656 reviews

Westwood cottage in garden setting

This 400 sq. ft. guesthouse (studio) on a historic property in Westwood, KS 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 kitchenette. 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.

Top guest favourite
A welcoming living room features a high ceiling with a large clock above the white brick fireplace. A comfortable sofa and plaid armchair are complemented by wooden coffee and side tables. Soft lighting is provided by two lamps, creating a relaxed ambiance.
Townhouse in Overland Park
4.94 out of 5 average rating, 203 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.

Top guest favourite
A spacious living area features a comfortable gray sofa placed on a soft area rug. Natural light fills the space, accentuating wood beams and a lofted area with a bed. A wooden coffee table and dining set complete the cozy atmosphere.
Home in Kansas City
4.96 out of 5 average rating, 248 reviews

Charming Waldo Reader's Retreat

When my husband & I first saw this house, I knew it was the perfect place to escape to do my favorite thing - read. I designed it with that in mind. I could see myself reading in front of the wood-burning stove. Reading on the martini deck with coffee in hand. Reading in the afternoon light in the loft or outside on the deck. Located in the heart of Waldo, walking distance to restaurants, bakeries and bars. Brookside/Plaza are minutes away. I hope you love it as much as I do, I know you will.

Guest favourite
A cozy living room is showcased with two brown leather sofas, a coffee table, and lamps on either side. A television is mounted on the wall opposite the seating. Natural light enters through two windows, while decorative items and plants add a welcoming touch.
Home in Olathe
4.83 out of 5 average rating, 100 reviews

Newly renovated - all amenities

Come and stay in our spacious & beautiful 1k sq ft apartment in the private, lower level of our home (we live upstairs). This space has been recently remodeled and has many sunny windows and great amenities for you. Our home is nestled in a popular Olathe neighborhood on a culture de sac that's known for safety and home town feeling. Guest have entire lower level to themselves. Host highly focused on great customer service and will always respond in a timely fashion to comments and questions

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
4.94 out of 5 average rating, 230 reviews

Cozy KC Carriage House

Unique former carriage house located in the Waldo neighborhood of Kansas City. 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 KC as well as Leawood, Prairie Village and Overland Park. Kansas City Registration No. NSD-STR-01359. Always ask for the short term rental registration so your stay isn't cut short with a compliance eviction by city enforcement.

Top guest favourite
A dining area is featured with a wooden table surrounded by four chairs. A colorful piece of wall art adds interest to the room. Opposite, a wooden sideboard displays dinnerware, while an open doorway leads to a comfortable living area with a sofa.
Home in Overland Park
4.96 out of 5 average rating, 197 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!

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, 239 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 serene bedroom space is presented with soft, neutral tones. A spacious bed is dressed with white linens, accompanied by decorative pillows. Natural light filters through sheer curtains, with a floral pendant light hanging above. A cozy blanket is casually draped over the bed.
Home in Prairie Village
4.95 out of 5 average rating, 130 reviews

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.

Guest favourite
An open-concept dining area is furnished with a large wooden table surrounded by six chairs. A modern chandelier hangs overhead, illuminating the space. In the background, a well-equipped kitchen features light grey cabinetry, stainless steel appliances, and a cozy living area with a comfortable sofa.
Home in Overland Park
4.91 out of 5 average rating, 109 reviews

Luxurious & Spacious Ranch 5BR with 2 King Beds

This stylish ranch home is perfect for groups or families. With multiple living spaces, our newly renovated home has room to spread out for fun or work and is equipped with 1Gb Wifi. Only MINUTES from Overland Park Convention Center, shopping center, and highway access to get anywhere quickly. Modern updates all throughout, plush beds with luxurious linens, fully stocked kitchen with laundry. A bar in the basement along with an air hockey table gives this place tons of fun entertainment.

Top guest favourite
The spacious basement living area features wood-paneled ceilings and soft carpeting. A round dining table with wooden chairs is positioned beside a cozy seating area that includes a couch and an armchair. A TV is mounted on the wall, offering entertainment options.
Home in Overland Park
4.95 out of 5 average rating, 436 reviews

Entire Private Basement with Walkout Entrance

Private basement with two queen beds, couch, memory foam cot or air mattress (upon request), full bathroom, washer/dryer, coffee maker, toaster, microwave, snacks, mini fridge (no freezer), table, WiFi, and a TV (Roku and antenna). We will be upstairs during your stay. We are not loud but you will hear us walk around upstairs. There is a walkout door to backyard. You will be able to park in the driveway. Walkway to gate located on east side of house. Walkway to backyard is well lit.

Top guest favourite
Home in Fairway
5 out of 5 average rating, 109 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!

Superhost
A gas log fireplace serves as the focal point, framed by a wooden mantel. Two Ethan Allen custom swivel chairs are positioned near a coffee table, all set against a neutral wall. A large television stands to the left, adding a cozy touch to the living area.
Flat in Grandview
4.75 out of 5 average rating, 158 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

Popular amenities for Leawood holiday rentals

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Frequently Asked Questions

  • Where should I stay in Leawood?

    Make yourself at home in Leawood by choosing from our most frequently booked neighborhoods. We have over 100 vacation rentals in Empire Estates, over 260 vacation rentals in Hawthorne, and over 1,550 vacation rentals in Corinth Hills.

  • Are there family-friendly vacation rentals in Leawood?

    Leawood has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Leawood have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Leawood. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Leawood have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Leawood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Leawood have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Leawood. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Leawood?

    Experience the best of Leawood with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there apartment rentals with a dedicated workspace in Leawood?

    Yes! Work meets play with ease at over 10 apartment rentals in Leawood featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Leawood have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Leawood. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly apartment rentals in Leawood?

    Four-legged friends are welcome in Leawood. Choose from more than 10 apartment rentals for guests traveling with pets.

  • What are the most popular amenities for Apartment Rentals in Leawood?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 $64 SGD 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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