Holiday rentals with outdoor seating in Prairie Village

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.

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

Private Retreat in Walkable Waldo Neighborhood

✔ Private detached home ✔ Free Parking ✔ Laundry Included ✔ 10–15 min to Plaza / Downtown ✔ Fast WiFi ✔ Quiet neighborhood Unique Carriage House in the Waldo neighborhood of KC a short drive to the streetcar, Plaza, Stadiums, Power & Light, Crossroads and Downtown as well as Leawood, Prairie Village and Overland Park. Highly rated, highly trusted local host. Always ask for the short term rental registration number so your stay isn't cut short with a compliance eviction by city enforcement.

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!

Top-Rated 4BR/Private Pool/Patio Perfect 4 Groups

World Cup oasis -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 April–late Sept/early Oct, weather permitting.

Sleeps 12! w/King Beds+Hottub+Gym+Theater

Relax in the #1 searched for neighborhood on Zillow in 2022! Our Prairie Village home has FAST 5GB Wifi, 4 bedrooms with top-notch mattresses, cozy duvet bedding, sound machines, & plenty of closet space. Our theater room can serve as a 5th BR & the sleeper sofa in the basement as a 6th BR! Enjoy the private hot tub, movie theater, backyard solo stove, gym & more. 🏟️ 22min from Chiefs/Royals 🏙️ 18min from the vibrant Downtown scene ☕️ Minutes from local favorite restaurants & PV shops!

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.

Modern Prairie Village Home

Nestled in the heart of Prairie Village, this delightful home was recently remodeled and is equipped with everything you need for the perfect stay. Enjoy luxury mattresses in the two bedrooms which are both equipped with TVs. Cozy up next to the fireplace with your favorite book or watch a movie on the living room tv. Play a round of foosball or shuffle board with the game on while your favorite dish is smoking in the Traeger outside. Walk to the Shops of Prairie Village within minutes.

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!

Prairie Village Modern Farmhouse! Great Location!

Enjoy your home away from home with style! This separate guest house has 1 bedroom & 1 bathroom that gives you privacy while still being centrally located in Prairie Village of Kansas City. Floor to ceiling shiplap walls, wood floors, black metal railing, & stylish decor you will feel like you're in an episode of Chip and Joanna Gaines' Fixer Upper! The home has its own private entrance, Washer/Dryer in unit and a fully functioning kitchen. High speed GooglFiber internet.

Perfect for Match Week | Easy Stadium Access

Coming to cheer at the FIFA World Cup 2026? Make this comfortable 3-bedroom Overland Park retreat your home base—close enough for match days, peaceful for downtime. -65” Smart TV w/streaming services + local channels -High Speed Wifi -6 min drive to downtown Overland Park -6 min drive to the Shops of Prairie Village -17 min drive to downtown Kansas City -22 min drive to GEHA Arrowhead Stadium -30 min drive to the airport rate (MCI)

Comfortable home~quiet neighborhood

Color and art create this comfortable space. Enjoy a nice walk around the neighborhood with easy access to Old Overland Park which is filled with quaint shops, restaurants, bakeries and an awesome farmer's market. Antioch Acres Park is just a few blocks away. Easy highway access to I35 and just 15 minutes from downtown Kansas City. Great for business professionals looking for a home away from home while traveling for work.