Pet-friendly holiday rentals in Olathe

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

Historic, Industrial Flat in the Heart of KC

Live the true Kansas-Citian lifestyle during your stay at this sparkling clean, private, and completely renovated 120-year-old brick beauty! Gorgeous hardwood floors, exposed brick walls, 11' exposed wood ceilings, 2 private decks, large gourmet kitchen, luxurious full bathroom, spacious master bedroom, and cozy 2nd bedroom. Located in the historic Westside of Kansas City; Walk seconds to neighborhood hot spots & minutes to KC's highlights: Crossroads, Street Car, Downtown & Convention Center.

The Mulberry House: Cozy Home In Downtown Olathe

- Adorable house on large lot (not a guest house/cottage) -60 ft driveway - Separate bedroom with smart tv, queen size bed (comfy memory foam mattress) - Living room with 55" smart TV, leather sofa and additional seating - Fully equipped kitchen w/ eating area - Full bathroom w/ tub/shower - Washer/dryer - Table with leafs converts to great office area - Deck w/ outdoor seating and grill - 20 min from the Plaza, Westport and Downtown, 30 min from Lawrence, 40 min from the airport - $25 pet fee

Johnson County Jewel

Welcome to our adorable, efficient 2 bedroom newly updated home with fenced yard for your fur baby. This is our home away from home. We hope you enjoy your stay with special features-like a great outdoor covered patio for playing oversized Jenga, cornhole or grilling up some KC BBQ! Centrally located off I-35 for easy dining, shopping & entertainment throughout Johnson County and Greater Kansas City. All new furnishings and fully stocked. King bed plus Daybed coverts to twins or another king!

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!

~Antioch Cozy Ranch~Pet Friendly~Central~Remodeled

🏠2 bedroom 2 bed 1 sectional 🛋 Maximum capacity 4 adults and 2 children 2 Smart TVs, Roku, Local Channels 1 bath Tub/Shower ✅ close to highways ✅ Ikea-2min, Plaza-15, Westport-10, airport-30.Restaurants/stores /places of entertainment ✅ Clean, suitable for families with children. We provide a high chair and a playpen ✅One level living, no stairs ✅ Garage for a medium/compact car, street parking available Parks, playgrounds, picnic shelters close ❌Pets must stay off furniture and beds

Private DayLight Basement, Own Entrance, 1800 s/f

Spacious & beautiful 1800 sq ft apartment, sanitized, private entrance w/smart lock, Lg open floor plan, furnished kitchen - appliances, dishes, cookware, own Laundry, bath rm w/2 sinks, 55" smart HDTV, 2 queen beds, one private bedroom, one open bedroom with curtain surround, private lower level of home, Many sunny windows, cul de sac, many restaurants & shops, 2 min to hwy 69, Driveway parking. Pets welcome, Pet rules are under Booking Settings, then House Rules.

Charming Basement Oasis

Pets- Dogs Only. Private basement suite with walk out entry, situated 1 mile from Historical Downtown Overland District. Within walking distance to South Lake Park. Basement suite is part of a single family home. The house is central air with thermostat located upstairs. Main level is occupied by residents & is separate from the basement suite. Suite includes full kitchen & laundry, full bathroom, walk in closet, one queen bed, & fold down sofa.

Home Away

Kick back and relax in this calm, stylish space containing all you need to make your stay home away. Located close to shopping malls, various food restaurants, fun interesting places to visit & adventure while accommodating both corporate business and leisure. Fast internet, fully stocked kitchen, bathroom and a dedicated work space. Access to a swimming pool, free gym, free parking, nature walk and a fenced dog park.

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.