Holiday houses 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.
Guesthouse in Westwood
4.99 out of 5 average rating, 655 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 private pool surrounded by a diamond cut concrete patio is visible. Lounge chairs and an umbrella provide shaded seating. The backyard is enclosed by a privacy fence, with the house in the background featuring multiple windows and a deck access.
Home in Overland Park
4.96 out of 5 average rating, 150 reviews

Kid-Friendly 4 Bedroom Home w/ Heated Private Pool

This 4 bedroom house is furnished perfectly for families & professionals. Plus, cool off in the relaxing private pool in the hot summer months! Located in a great neighborhood, walking distance and/or short drive to dining, shopping, and golf courses. Home features 4 bedrooms (2 en suite), 3.5 baths, fully equipped kitchen & large laundry/mud room. Two living spaces & tons of room for indoor and outdoor entertainment. Pool opens early April, closes late Sept to early Oct, weather dependent.

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.

Guest favourite
A spacious sleeping area features a queen-size bed dressed in soft linens and a blue sofa, along with a coffee table. A smart TV is mounted on the wall, and a desk is positioned in the adjacent office area, illuminated by natural light from nearby windows.
Home in Mission
4.93 out of 5 average rating, 378 reviews

The Little House: Cozy Home in Overland Park

- Adorable house on large lot (not a guest house/cottage) - 110 ft Driveway - Sleeping quarters with queen size bed (comfy memory foam mattress) - Living room with 40" smart TV, sofa-sleeper and additional seating - Fully equipped kitchen w/ eating area - Full bathroom w/ clawfoot tub/shower - Sunroom w/ seating area and daybed - Washer/dryer - Office area w/ desk - Deck w/ outdoor seating and grill - 10 min from the Plaza, 15 min from Westport and Downtown, 25 min from the airport - $25 pet fee

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, 229 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.

Guest favourite
A cozy living area is highlighted by a large wall mural featuring trees and soft light. A sectional sofa and an armchair provide comfortable seating. A small coffee table sits on a patterned area rug, while a television and a work desk are positioned nearby.
Home in Overland Park
4.94 out of 5 average rating, 530 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.

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, 195 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 broad driveway leads to a spacious building featuring a mix of brick and blue siding. Two garage doors are visible, framed by landscaped green areas and decorative fencing. The serene surroundings are complemented by trees in the background, creating a peaceful entrance.
Barn in Greenwood
4.91 out of 5 average rating, 189 reviews

Cozy private cottage/studio

Private studio on the second level of our detached garage behind our main house. Located in a resort-like property. Quiet and safe neighborhood. Minutes from downtown Lee's Summit. Coffee shop/bakery within walking distance. Several restaurants close by, 1 mile to iconic antique malls. Perfect place for traveling professionals. Close to Hwy 291. We use the garage for storage and to work on our vehicles occasionally, you might hear us working. *There is no smoking/vaping in the apartment*

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, 129 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.

Top Guest favourite
Home in Fairway
5 out of 5 average rating, 108 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!

Popular amenities for Leawood holiday rentals

When is the best time to visit Leawood?

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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 Hallbrook, over 1,550 vacation rentals in Corinth Hills, and over 100 vacation rentals in Empire Estates.

  • 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 house rentals in Leawood have wifi?

    Absolutely! We offer over 10 house 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 apartment rentals in Leawood have a kitchen?

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

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

    Experience the best of Leawood with our house 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 wifi, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with air conditioning, 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 $86 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Leawood holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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