
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.

Luxury Retreat 1 block to downtown OP
Looking for better than average? Designed as a comfortable, relaxing, model smart home with the latest features. For the perfectionist that seeks a better stay for work, play or relaxing. Eating healthy? Masticating Juicer, & Ninja. Coffee? French Press, Coffee Grinder, Nespresso, & Keurig. Clean, comfortable, peaceful and one block to downtown Overland Park. Gel, memory foam mattress. Low profile shower w/ handheld. Grout free, clean, Onyx shower. HVAC has UV, Ozone & bio-scrubber. Outdoor pa

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.

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.

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.

Secret Garden Short Stay
1 King Bed. 1 Twin air mattress rollaway (plz req rollaway) Washer/Dryer for your use. Wi-Fi Fiber. Sep. fenced backyard area with Priv. entry into your basemnt area that is located around the back of our main house. Parking space on prop. Dog park, walking trails. Pet fee is charged. Close to highwy, & shopping. We also have Solar panels that provide some back up for the heat/air and refrig. Entire daylight basement is separate from us upstairs with locked door. Does have couple of steps.

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.

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-Rated 4BR/Private Pool/Patio Perfect 4 Groups
World Cup oasis -4-bedroom home with heated private pool, ideal for families and professionals. Comfortably sleeps up to 10 guests and is a great home base for out-of-town visitors attending World Cup matches or watching the games during downtime. Located in a desirable neighborhood close to dining, shopping, and golf. Features 4 bedrooms (2 en suite), 3.5 baths, a fully equipped kitchen, large laundry room, and two living spaces. Pool open April–late Sept/early Oct, weather permitting.

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!

Prestige-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!

Home Away
Kick back and relax in this calm, stylish space containing all you need to make your stay home away. Located close to shopping malls, various food restaurants, fun interesting places to visit & adventure while accommodating both corporate business and leisure. Fast internet, fully stocked kitchen, bathroom and a dedicated work space. Access to a swimming pool, free gym, free parking, nature walk and a fenced dog park.

The Black Walnut KC Pool House & Hot Tub
New pool house that sleeps up to 5 with two amazing king size beds and a pull out couch along with a beautiful full bathroom. Artificial pet friendly grass, heated pool, and hot tub that open year round make this a unique resort style stay in the heart of the favorite neighborhood of all of Kansas City - Brookside! We do not do parties or events, but love your furry family! @theblackwalnutkc
Popular amenities for Leawood holiday rentals
Other great holiday rentals in Leawood

The Travel House 435 Overland Park

The Evergreen Retreat

Charming Bungalow with Spacious Yard

*Walk to Downtown OP*/Pet Friendly

The Cabin

Beauty in Overland Park!

Comfy Hideaway in Merriam

Grace House, quiet, it has heating, hot water
When is the best time to visit Leawood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $89 AUD | $92 AUD | $95 AUD | $99 AUD | $112 AUD | $103 AUD | $102 AUD | $110 AUD | $103 AUD | $109 AUD | $103 AUD | $105 AUD |
| Avg. temp | -2°C | 1°C | 7°C | 13°C | 18°C | 23°C | 26°C | 25°C | 20°C | 14°C | 6°C | 1°C |
Frequently Asked Questions
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.
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 pet-friendly vacation rentals in Leawood?
Four-legged friends are welcome in Leawood. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Leawood?
Yes! Work meets play with ease at over 10 vacation rentals in Leawood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Leawood?
Make yourself at home in Leawood by choosing from our most frequently booked neighborhoods. We have over 360 vacation rentals in Hawthorne, over 1,840 vacation rentals in Corinth Hills, and over 130 vacation rentals in Empire Estates.
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.
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.
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.
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 free parking, over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Leawood

Total holiday rentals
Explore 30 holiday rentals in Leawood

Nightly prices starting at
Leawood holiday rentals start at $71 AUD 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 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Leawood holiday rentals include Wi-Fi 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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