
Holiday rentals with a pool in Overland Park
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Overland Park
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Ranch Getaway w/ Pool, Game room, Fire pit
Welcome to Bar Dot Ranch, a peaceful retreat on 15 acres in Kansas City, Kansas. This charming 3-bedroom, 2 1/2 bathroom home sleeps up to 10 guests and offers modern comforts with a cozy ambiance. Enjoy wildlife sightings and relax with our new Cowboy Pool open May - Oct, or have fun indoors with the pool table and arcade games. Just a short drive to the Legends district and Kansas City Speedway, Bar Dot Ranch combines country tranquility with city convenience. Book now for the perfect getaway!

KC themed 2 BR,1 BA townhome w/infinity game table
Welcome to our newly remodeled, fun, Kansas City themed, ranch layout townhome! Featuring 2 bedrooms, 1 bathroom and a TV/Game den with comfortable couch that can convert to a queen size bed. Fully equipped kitchen, washer/dryer, Smart TV's, WiFi with streaming capabilities, Infinity Game Table with multiple games to choose from, outdoor grill and patio set, tennis/basketball court in the neighborhood (equipt. in the shed) and 4 shared pools, available seasonally. Safe location, 5 min from I-35.

Cozy home, work/play, easy access to all things KC
The Harris House is a real gem nestled in the heart of Historic DT Lee’s Summit! Just steps away, enjoy shopping, restaurants/bars, coffee shops, Farmer’s Market, & much more! Across the street is Harris Park & Summit Waves water park! Catch a train ride on the Amtrak, or just enjoy the nostalgic sound of the trains as they travel thru this quaint little town! Perfect space for out of town work! Easy hi-way access to Chiefs & Royals stadiums, DT KC, The Plaza, about 20 min from everything KC!

Private Pool Retreat/Stylish 4BR Getaway/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.

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.

Tiki Lounge • Sauna • Pool • Designer KC Bungalow
A 125-year-old bungalow packed with personality. Inside you’ll find curated worldly décor, many lounge spaces, and the house’s most famous feature: the Lucky Kitty Tiki Lounge, a hidden bar built inside the old garage. Outside, relax in the barrel sauna, cold plunge, and stock tank pool, gather around the fire pit, and unwind under the string lights after a night exploring Kansas City. It’s a one-of-a-kind stay just minutes from downtown, the stadiums, and some of the city’s best restaurants.

The Cabin
Escape to tranquility! This tiny modern home, sits on a slow moving stream. The perfect blend of nature and luxury. Nestled on 20 lush acres surrounded by trees. Enjoy a full kitchen, washer/dryer, dishwasher & an outdoor fire pit. Private access to pool (staying guests only) , basketball court & a regulation pickleball court. Just 5 miles from the Bourgmont Winery & minutes to the Overland Park Arboretum. Kid tent party option , additional cost per guest. Horses do roam the open field.

KC Apt River Market - 104
Clean and convenient 1 bedroom apartment. 20 minutes Airport & 8.7 miles to Stadium. Located in the vibrant, creative and diverse River Market community with access to many attractions and entertainment areas of Kansas City. Take the free streetcar to Union Station, Crossroads, Power & Light District/T-Mobile Center, Convention Center and more. Your stay includes pool and fitness center access, as well as a community rooftop courtyard with skyline views. Close the KC Current soccer.

Amazing House with Heated Pool & Rooftop Hot Tub!
Experience an exceptional stay at our Kansas City vacation rental. Whether it's the stunning views, the year-round heated saltwater pool and hot tub access, or the top-notch furnishings and bedding; We have everything to make your stay unforgettable. Our well-appointed furnishings, bedding, and mattresses ensure your comfort during your stay. Come and enjoy the best that Kansas City has to offer! **3-night minimum on weekends/ 2-night minimum on weekdays/strict no-party policy.**

Vibrant remodeled 3 bedroom townhome
Newly remodeled vibrant and stylish townhome. Featuring 3 bedrooms and 1 bathroom. Fully equipped kitchen, onsite washer/dryer, smart TVs, high speed WiFi with streaming abilities, coffee bar, grill, outdoor patio with seating, and access to 4 neighborhood outdoor pools(seasonal - typically Memorial Day thru Labor Day), tennis courts, and other amenities. Located in a safe and quiet neighborhood in Lenexa with easy access to both interstate I35 and I435.

World Cup Luxury in Lenexa w/hot tub Sleeps 10
Enjoy comfort and style in this spacious, unique home in Lenexa, Kansas. If you're looking for a 10/10, you’ve found it! The living room features beautiful beams, an electric fireplace, and patio access to the heated pool(closed Nov1-March31). Upstairs is a stunning master suite with heated floors and two more updated bedrooms. Step outside to your private oasis with a heated pool and hot tub. Ask us about our special offer!

The Nest Villa with Pool in Kansas City
This spacious, just updated home is located North of KCMO and minutes away from all major Shops and Restaurants. With 3 bedrooms, 3 beds & 2 baths, this home has plenty of space for families and friends. 15 mins to the Airport 15 mins to Downtown KC 15 mins to World of Fun/Ocean of Fun 15-20’ to T-Mobile Center, KC Convention Center. Short drive to KC Plaza, UMKC, Crown Center, National WWI Museum & so much more!
Popular amenities for Overland Park rentals with a pool
House rentals with a pool

Sports house in Olathe

Modern Home with shipping Container Pool

Secluded•Hot Tub• Outdoor Cinema•Pool•The Spot

Spacious Lenexa Townhouse w/ Pool/Ping-Pong Table

Mimi's Place: 3BR Home Near KC Weddings + WC26

Kelz-Cute & comfy. DTLS & KC Chiefs/World Cup

Stay at Whispering Pines

KC Group Retreat | Sport Court, Golf, Gym, SwimSpa
Other holiday rentals with a pool

Cozy, Comfy, & Convenient - 1 Bedroom - Sleeps 4

Cozy Townhome In Lenexa:Sleeps 5:Community Pool

Bright & clean 2BR/1.5 bath Lenexa townhouse

Spacious & Updated Getaway! Pool & Hot Tub 10 Beds

Overland Park Condo, Close to Lakes & Parks!

Heated All season pool Private Spacious King bed

The Bungalow at the Dugan Lagoon! Come relax!

Luxury Modern KC Home | Olathe | Overland Park
When is the best time to visit Overland Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $257 AUD | $270 AUD | $245 AUD | $248 AUD | $205 AUD | $212 AUD | $218 AUD | $207 AUD | $175 AUD | $202 AUD | $218 AUD | $212 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 |
Quick stats about holiday rentals with a pool in Overland Park

Total holiday rentals
Explore 70 holiday rentals in Overland Park

Nightly prices starting at
Overland Park holiday rentals start at $58 AUD per night before taxes and fees

Verified guest reviews
Over 2,450 verified reviews to help you choose

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

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Overland Park rentals

4.7 Average rating
Overland Park stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- St. Louis Holiday rentals
- Kansas City Holiday rentals
- Branson Holiday rentals
- Oklahoma City Holiday rentals
- Lake of the Ozarks Holiday rentals
- Omaha Holiday rentals
- Tulsa Holiday rentals
- Central Illinois Holiday rentals
- Bentonville Holiday rentals
- Platte River Holiday rentals
- Wichita Holiday rentals
- Des Moines Holiday rentals
- Family-friendly rentals Overland Park
- House rentals Overland Park
- Rentals with a hot tub Overland Park
- Rentals with a fire pit Overland Park
- Townhouse rentals Overland Park
- Pet-friendly rentals Overland Park
- Apartment rentals Overland Park
- Rentals with outdoor seating Overland Park
- Rentals with an EV charger Overland Park
- Condo rentals Overland Park
- Rentals with breakfast Overland Park
- Fitness-friendly rentals Overland Park
- Rentals with a washing machine and dryer Overland Park
- Rentals with a patio Overland Park
- Rentals with a fireplace Overland Park
- Private suite rentals Overland Park
- Rentals with pools Johnson County
- Rentals with pools Kansas
- Rentals with pools United States
- 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
- T-Mobile Center
- Union Station
- University of Kansas - Lawrence Campus
- Uptown Theater
- National World War I Museum and Memorial
- Overland Park Arboretum & Botanical Gardens
- Science City at Union Station
- Kauffman Center for the Performing Arts
- Midland Theatre
- Hyde Park
- Crown Center
- Bartle Hall
- Kansas City Power & Light District




