
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.

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.

Modern Madison - Near Downtown & Crossroads
Are you looking for a one-of-a-kind stay? Our property is like no other. Awarded by the prestigious American Institute of Architects and featured in various magazines, it's a modern, minimalistic and sustainable home. Everything is fully electric - powered by solar panels - reducing carbon footprint. It's located in the trendy Westside neighborhood, just steps away from Downtown & Crossroads. Make your stay a memorable one & enjoy the Modern Madison experience. Thank you for considering us!

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.

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.

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.

Wonderful Waldo Bungalow
Darling bungalow recently remodeled/updated. Very quiet street 3 blocks off Wornall Rd. 1 mi. from Ward Pkwy Center - shops/restaurants/theater. 3 mi. to Brookside, 5 mi. to Plaza. Lg fenced backyard. Carport. Coffee, toiletries, new sheets and towels for your enjoyment. We love this home and believe you will find your stay enjoyable. Home was built in the 50's and has all the charm you would expect! If traveling with pets, the must be pre-approved and pet cleaning fee agreed upon.

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.

Charming Home in heart of KC
Enjoy midwest hospitality at this charming FAMILY-FRIENDLY home, conveniently located in a beautiful area of KC—3 mi to the Plaza, min away from Prairie Village shops & restaurants, & walking distance to the Fairway Creamery— where you can enjoy breakfast or a sweet treat. See the sites or relax at home with two 75" TVs in a quaint, peaceful neighborhood. NO PARTIES or EVENTS as per Airbnb rules. Walking distance to tennis courts, pool, and parks.
Popular amenities for Leawood holiday rentals
Other great holiday rentals in Leawood

Modern Chic Loft | Shawnee KS

Light Room Stylish Work Loft Nr Global Sports Fun

Modern Craftsman Home in Walkable Waldo

Historic Charm: Spacious 4BR Retreat Sleeps 11

Spacious 4 BR house; minutes to World Cup shuttle!

Grace House, quiet, it has heating, hot water

20 mins to Chiefs & Sporting KC -Cozy 3BR~2BA

Luxurious & Spacious Ranch 5BR with 2 King Beds
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 | $93 AUD | $96 AUD | $100 AUD | $113 AUD | $104 AUD | $103 AUD | $112 AUD | $104 AUD | $110 AUD | $104 AUD | $106 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
- Science City at Union Station
- National World War I Museum and Memorial
- Hyde Park
- Kauffman Center for the Performing Arts
- Midland Theatre
- Bartle Hall
- Overland Park Convention Center
- Crown Center




