Vacation rentals in Roeland Park

Charming Cottage 3bed 2bath firepit near Plaza

Nothing says home sweet home like this Charming Kansas City Cape Cod Cottage. 3 bedroom, 2 bathroom home, screened in porch, fenced in big backyard, tree-lined quiet street, and full kitchen. Enjoy a walk to our local coffee shops Hi Hat & Front Range, bookstore, grocery, park, and restaurants. Centrally located so you can explore all of the very best KC has to offer- Country Club Plaza, Westport, Union Station, KU Med, TMobile, Crown Center, Power & Light, museums and The Chiefs at Arrowhead!

Comfy, quiet & private 2BR home.

Discover comfort and convenience at our charming home in the heart of Kansas City. This two-bedroom, one-bathroom home boasts a fully equipped kitchen and stylish furnishings. Centrally located, it offers easy access to the Kansas City Metro area. Nestled on a quiet and peaceful cul-de-sac, you'll enjoy tranquility and relaxation after exploring the city. During warmer months, unwind in the well-manicured lawn. Make your stay memorable in this centrally situated haven with the comforts of home.

1-bedroom 2nd floor suite w/private entrance!

We feature a smoke- and vape-free home and property. We also have a 2-bedroom listing. Leafy, close-in KS suburb. Apartment on 2nd floor of our home + DECK. Off-street parking for 1 car. Well-lit PRIVATE entrance. Microwave, mini-fridge, coffeemaker, kettle, toaster oven. Coffee, tea; Self-check-in for late arrivals. Very walkable neighborhood just 15 min. from Downtown, KU Med Center, Plaza, galleries, T-Mobile Center. Nearby locally-owned restaurants, coffee shops, parks, IKEA.

Private Penthouse +Balcony Overlooking 39th Street

Located atop the Meshuggah Bagels along the iconic West 39th Street, this renovated 3rd level flat is truly an urban oasis. Guests are treated to comfortable accommodations with private access to your own balcony overlooking 39th Street! Get a glimpse of Kansas City through the eyes of a local! Be sure to check out the virtual guide book full of local restaurants, shops, and nightlife. There’s something for everyone. From global cuisine to barbecue, shopping and more!

Cozy home, great for families and friends

Great location, perfect for groups or families. Whether you are traveling for work or pleasure this house will fit your needs to stay with comfort!! Easy access to I35, minutes from the Plaza, Westport or downtown KC. Enjoy this quiet street with lots of birds and and a beautiful old oak tree. Driveway accommodates four vehicles and there is also street parking. Possible to live on one level with a single step to enter the house. License Number RL18-000148

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.

~Great Location | Game Room | Easy Self Check-in~

This beautifully updated and decorated home is perfect for families, couples getaway or business professionals. Complete with 2 living room spaces and a game room, it is sure to entertain the whole family. You will be centrally located just minutes from Overland Park's historic downtown area as well as The Prairie Village Shops with an array of dining options, shopping and activities.

Modern Luxury KC Oasis w/Fire Pit Near KU Med

Welcome to your modern urban retreat located in Kansas City's vibrant Rosedale neighborhood. This 3-bedroom, 2-bathroom home is designed to provide you with luxurious comfort and eco-friendly style, making your stay truly exceptional. ⭑CONTACT US FOR SEASONAL DISCOUNTS⭑ ⚽️⚽️ WELCOME TO KANSAS CITY WORLD CUP 2026 TEAMS & TICKET HOLDERS ⚽️⚽️

Adorable Roeland Park Ranch + Pet Friendly!

Welcome to The Checkmate – Your Perfect Stay in Roeland Park! The Checkmate is a thoughtfully designed two-bedroom ranch home nestled in the charming and quiet neighborhood of Roeland Park, KS. Whether you're visiting for work, relaxation, or a little of both, this home offers the perfect blend of comfort, convenience, and style.