
Holiday houses in Overland Park
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Top-rated holiday rentals in Overland Park
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.

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

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.

Stylish 1 bedroom, 1 bath custom apartment home
Completely remodeled, stylish apartment home in the heart of downtown Overland Park. Conveniently located 4 blocks from downtown Overland Park's entertainment district with many unique shops & restaurants. Walk across the street to Burg & Barrell for great food or a craft beer. Short walking distance to CVS Pharmacy, Hawaiian Bros, Dollar Tree, Metcalf Liquors & Price Chopper. Centrally located and only 15 minutes from The Country Club Plaza or Downtown Kansas City. *This is an upstairs unit.

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.

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.

Secret Garden Short Stay
1 King Bed. 1 Twin air mattress roll away (plz req rollaway) Washer/Dryer for your personal use. Fast Wi-Fi Fiber. Sep. fenced off backyard area with Private entry into your basement area that is located around the back of the main house. Parking space on property. Dog park, walking trails. Restaurants close by. Close to highwy, gas stations and shopping. We also have Solar panels that provide some back up for the heat/air and refrig if electricity goes out!!!
Popular amenities for Overland Park holiday rentals
Stay near Overland Park's top sights
Other great holiday rentals in Overland Park

Charming King Bedroom in Shawnee

Stay w Superhost Overland Park KS/Kansas City

Private bedroom, bath, family room .

Ping pong and sleep. (No stairs)

Perfect & Private Mother-in-law Suite

World Cup Squad Overland Park, sleeps 8

Queen bedroom with bath in safe suburb

The Leaning Chimney Loft with a private entrance!
When is the best time to visit Overland Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $208 NZD | $210 NZD | $224 NZD | $220 NZD | $238 NZD | $250 NZD | $241 NZD | $238 NZD | $232 NZD | $224 NZD | $231 NZD | $224 NZD |
| 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 Overland Park?
Make yourself at home in Overland Park by choosing from our most frequently booked neighborhoods. We have over 2,010 vacation rentals in Shawnee Mission, over 150 vacation rentals in Nottingham Forest, and over 1,280 vacation rentals in Mission.
Are there vacation rentals with a dedicated workspace in Overland Park?
Yes! Work meets play with ease at over 420 vacation rentals in Overland Park featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Overland Park?
Four-legged friends are welcome in Overland Park. Choose from more than 270 vacation rentals for guests traveling with pets.
Are there Overland Park vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Overland Park, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Overland Park have wifi?
Absolutely! We offer over 60 apartment rentals with wifi in Overland Park. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Overland Park have a bbq area?
Absolutely! We offer over 100 house rentals with a bbq area in Overland Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Overland Park have a gym?
Absolutely! We offer over 20 apartment rentals with a gym in Overland Park. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in guesthouse rentals in Overland Park?
Experience the best of Overland Park with our guesthouse 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 family-friendly townhouse rentals in Overland Park?
Overland Park has more than 40 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do condo rentals in Overland Park have air conditioning?
Absolutely! We offer over 10 condo rentals with air conditioning in Overland Park. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Overland Park

Total holiday rentals
Explore 710 holiday rentals in Overland Park

Nightly prices starting at
Overland Park holiday rentals start at $34 NZD per night before taxes and fees

Verified guest reviews
Over 45,120 verified reviews to help you choose

Family-friendly holiday rentals
480 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 270 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
420 properties have a dedicated workspace

Wi-Fi availability
700 of Overland Park holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Overland Park rentals

4.8 Average rating
Overland Park stays are highly rated by guests—averaging 4.8 out of 5!
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