Pet-friendly holiday rentals 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

Secret Garden Short Stay

1 King Bed. 1 Twin air mattress rollaway (plz req rollaway) Washer/Dryer for your use. Wi-Fi Fiber. Sep. fenced backyard area with Priv. entry into your basemnt area that is located around the back of our main house. Parking space on prop. Dog park, walking trails. Pet fee is charged. Close to highwy, & shopping. We also have Solar panels that provide some back up for the heat/air and refrig. Entire daylight basement is separate from us upstairs with locked door. Does have couple of steps.

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!

Historic, Industrial Flat in KC

Live the true Kansas-Citian lifestyle in this sparkling clean, and completely renovated 120-year-old brick beauty! Gorgeous hardwood floors, exposed brick walls, 10' island in the gorgeous chef's kitchen featuring gas cooktop and built-in oven/microwave. Spa-like bathroom with heated floors and rain shower head in the frameless glass shower. Spacious master bedroom with desk. Private rear deck and shared backyard. Walk minutes to KC's highlights: Crossroads, Street Car & Ferris Wheel!

The Nelson & Plaza Condo w/ free parking!

🚆 STREETCAR OPEN! (see map) 📍Your Kansas City getaway begins here overlooking the Nelson and minutes from the Plaza! 🛏 1 bedroomQueen bed 🛏 1 futon 🛁 1 bath w/jacuzzi tub 🚶‍♂️ Plaza (10min walk) 🚶‍♀️ Nelson (5 min) 🚶‍♀️ BBQ (10 min) 🚗 Arrowhead Stadium (15 min) 🚗 KC Zoo (12 min) 🚗 Power&Light (11 min) 🚗 Union Station (11min) ✅ 1 Designated Parking spot ✅ Rooftop & Gym ✅ 1 pet for $45 fee (HOA DOES NOT ALLOW PET>30LB) ✅ In unit laundry ✅ Coffee, Tea, & Snacks

Chic Modern Home in Downtown Overland Park

Chic modern stay in the heart of Downtown Overland Park! Relax with a plush king and queen bed, 1Gbps fast Wi-Fi, & washer/dryer. Walk to cafes, bars, shops, & the farmer’s market. Just 15 min to Plaza/downtown KC, 25 min to Arrowhead/MCI airport. Fully equipped kitchen & parking included. Perfect for couples or small groups (sleeps 4 w/ a queen air mattress available upon request). Book now for a comfy, convenient getaway that blends style & location—your ideal home base!

Coho (Cozy Boho) Carriage House, Near Plaza

Come experience this century old, newly renovated carriage house right in the heart of Kansas City! With extremely close proximity to the city’s favorite destinations, this historic abode will help make your stay convenient and cozy. Locations and their distances from where you'll be: - The Nelson-Atkins Museum - 1.6 Miles - The Plaza - 1.7 Miles - Kansas City Zoo - 4 Miles - Union Station - 4.6 Miles - Downtown - 5.1 Miles - Chiefs & Royals Stadiums - 5.6 Miles

Perfectly Located Carriage House Apartment

1 BR loft apartment in centrally located Westwood. Walk to restaurants, groceries, and shops, including Joe's KC BBQ and LuLu's. Close to Plaza, Westport, and downtown/crossroads. Pets ONLY considered for week long stays and longer. As always, the apartment will be spotlessly clean using disinfectant and bleach-based cleaners. We will block 24 hours between stays to ensure the apartment has fully circulated. Virus-grade HVAC filters have also been installed.

Charming Home in heart of KC

Enjoy midwest hospitality at this charming FAMILY-FRIENDLY home, conveniently located in a beautiful area of KC—3 mi to the Plaza, min away from Prairie Village shops & restaurants, & walking distance to the Fairway Creamery— where you can enjoy breakfast or a sweet treat. See the sites or relax at home with two 75" TVs in a quaint, peaceful neighborhood. NO PARTIES or EVENTS as per Airbnb rules. Walking distance to tennis courts, pool, and parks.

Charming Waldo Reader's Retreat

Sweet little bungalow in the heart of Waldo. Sits at the back of the property, so there is no fenced in yard. We had a new driveway poured in 2025, you’re welcome to use that or park on the street. Main bedroom is on the ground floor with an additional bed upstairs (the stairs are ladder-like, so not suitable for everyone!). We love this little house so much and think you will too.

Adorable Roeland Park Ranch + Pet Friendly!

🏡 Charming Roeland Park 2-bedroom ranch (1 King, 1 Queen + Queen daybed) 🛁 1 full bathroom with luxury Tommy Bahama products ☕ Fully equipped kitchen with upgraded coffee bar 🛋 Cozy living room with Smart TV + board games 📶 High-speed WiFi, USB charging stations 🌳 Private deck, pet-friendly, driveway parking 📍 Minutes from Country Club Plaza, Downtown KC, local shops & parks