
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.

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.

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

Art-filled Retreat w/ King Beds & Private Patio
Unwind at this art-filled, newly renovated townhouse minutes from restaurants, shopping and entertainment. Two king bedrooms with smart TVs make for a great getaway for two couples or a small family. Enjoy the fully-equipped kitchen or grill on the private patio. The basement serves as a lounge and office space and is equipped with a TV, sofa, desk, laundry room and full bath. Walk to the community pool or hit the courts for a game of basketball, tennis, or pickleball with provided equipment.

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.

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.

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.

Private Penthouse +Balcony Overlooking 39th Street
Located atop the Meshuggah Bagels along the iconic West 39th Street, this renovated 3rd level flat is truly an urban oasis. Guests are treated to comfortable accommodations with private access to your own balcony overlooking 39th Street! Get a glimpse of Kansas City through the eyes of a local! Be sure to check out the virtual guide book full of local restaurants, shops, and nightlife. There’s something for everyone. From global cuisine to barbecue, shopping and more!
Popular amenities for Leawood holiday rentals
Other great holiday rentals in Leawood

Charming King Bedroom in Shawnee

Golf View Lake View full Apartment

Stay w Superhost Overland Park KS/Kansas City

Santoclere - designer home at Corporate Woods

Sinatra Escape King Bed WiFi & Global Match Energy

Grace House, quiet, it has heating, hot water

The Leaning Chimney Loft with a private entrance!

30+ Days only w/King Beds+Hottub+Gym+Theater
When is the best time to visit Leawood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $95 AUD | $98 AUD | $101 AUD | $105 AUD | $119 AUD | $110 AUD | $108 AUD | $117 AUD | $110 AUD | $101 AUD | $105 AUD | $99 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
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 $75 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 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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