Holiday rentals with outdoor seating in Prairie Village

Luxury Retreat 1 block to downtown OP

Looking for better than average? Designed as a comfortable, relaxing, model smart home with the latest features. For the perfectionist that seeks a better stay for work, play or relaxing. Eating healthy? Masticating Juicer, & Ninja. Coffee? French Press, Coffee Grinder, Nespresso, & Keurig. Clean, comfortable, peaceful and one block to downtown Overland Park. Gel, memory foam mattress. Low profile shower w/ handheld. Grout free, clean, Onyx shower. HVAC has UV, Ozone & bio-scrubber. Outdoor pa

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

Where's Waldo? - Garage Loft

This tiny loft apartment is located in an old neighborhood with big trees, and just a short walk away from Waldo shops, restaurants and bars. Easy travel to Westport, Country Club Plaza, Crossroads, River Market, Power & Light, and many more super fun KC gems. The apartment is in the space that once was our old garage, so it's attached to our home. You have a separate and private entrance, full bath with an amazing shower, a small kitchen with appliances, and a loft bedroom with ladder access.

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!

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.

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!

Backyard Artist Studio near Plaza

Backyard Artists Studio! *Pet Friendly* Walking distance to shopping and nightlife districts The Plaza and Westport. 200 sqft tiny living in a quiet backyard at the heart of Kansas City. Located close to everything KC has to offer. We are experts in all things Kansas City. This woodworking shop was turned into a cozy tiny home for artists. It boasts rustic exposed wood ceilings, a vintage kitchenette, patio deck, and comfortable mattress. Same day check-in time is after 6pm.

Cozy KC Carriage House

Unique former carriage house located in the charming Waldo neighborhood of Kansas City. 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.

Cheerful 3 bedroom fully renovated cottage home

The Hadley cottage is a great place to bring the family for a fun get-a-way or perfect for your work needs. This chic & modern cottage is 3 minutes from I-35 and conveniently located to get you anywhere in the KC metro quickly. This is a quiet neighborhood with wide sidewalks within walking distance to restaurants or shopping. The cottage features a renovated interior in 2022, huge fenced backyard, and a long driveway for ample parking.

Travel-Ready Home | Safe Area, Easy Stadium Drive

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)

Chateau Waldo - Cuddle-up Charming Home

Now booking for the World Cup! Our home is just 15 minutes from the soccer stadium!! Come stay at our charming updated Waldo retreat located in the heart of Kansas City! As a young couple starting out, my wife and I renovated this sweet home and made it beautiful. This lovely two-bedroom house features a remodeled kitchen and bathroom, office space, and a custom built screened in outdoor back patio. KC License # NSD-STR-00929