
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.

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.

Luxury 4BR Oasis w/ Private Pool – Top Rated
World Cup–ready 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 early April–late Sept/early Oct, weather permitting.

The Resting Place, Grandview Home-Upper Level
Beautiful home in safe, quiet neighborhood. This listing is for the Upstairs Level of Home only, as seen in pictures & described, includes 3 bedrms/2 baths. Upstairs Level is completely separate & secure from Lower Level of home, with own separate entrance. Lower level may have other guests staying. To book the whole house, please book res. for the Upper and Lower separately. For Lower, search: The Resting Place, Grandview Home-Lower Level. *Please review house rules prior to any booking.

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!

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!

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.

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!

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.

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.

Cozy home-away-from-home. You won't want to leave!
Peaceful Red Door Inn--plenty of room to stay a few days. You have the whole house! Visit the wonderful Kansas City area, or stay home with the screened-in porch & quiet backyard for a restful getaway or retreat. Dozens of restaurants minutes away or fully equipped kitchen for your use with grocery stores only blocks down the street. WiFi & cable with Showtime included.
Popular amenities for Leawood holiday rentals
Other great holiday rentals in Leawood

Modern Luxe Ranch - Downtown OP

Quiet Large 4BR Home w/ Easy Access to highways

Spacious 5BR in OP | EV Charger

The Cabin

Sunflower Suite- Central,Near golf course & HWY

World Cup Luxury in Lenexa w/hot tub Sleeps 10

Leaned Cottage cozy relax Soccer CUP26

3BR 3BA Fairway Home • Dog-Friendly • Fenced Yard
When is the best time to visit Leawood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $90 AUD | $92 AUD | $95 AUD | $100 AUD | $112 AUD | $104 AUD | $102 AUD | $111 AUD | $104 AUD | $110 AUD | $104 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 apartment rentals in Leawood?
Experience the best of Leawood with our apartment rentals, starting at about $50 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 290 vacation rentals in Hawthorne, over 1,590 vacation rentals in Corinth Hills, and over 110 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 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.
What are the most popular amenities for House Rentals in Leawood?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, 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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- GEHA Field at Arrowhead Stadium
- Oceans of Fun
- Kauffman Stadium
- Kansas City Zoo
- LEGOLAND Discovery Center Kansas City
- The Nelson-Atkins Museum of Art
- Snow Creek Ski Area - 2022 OPEN WEEKENDS
- Kansas City Convention Center
- Jacob L. Loose Park
- Negro Leagues Baseball Museum
- Legends Outlets Kansas City
- Union Station
- T-Mobile Center
- University of Kansas - Lawrence Campus
- Uptown Theater
- Overland Park Arboretum & Botanical Gardens
- National World War I Museum and Memorial
- Science City at Union Station
- Hyde Park
- Kauffman Center for the Performing Arts
- Midland Theatre
- Bartle Hall
- Crown Center
- The Ewing And Muriel Kauffman Memorial Garden




