Holiday rentals in Roeland Park

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

By Famous Plaza+Near DT 1BR APT w/ KTCHN+WorkSpace

🌃⭐Embrace comfort and convenience in our 1-bedroom Plaza oasis⭐🌃 Nestled in KC's premier shopping and dining district, this Airbnb offers comfort and style. Enjoy a short walk to the Plaza's renowned shops, restaurants🍝, and entertainment options👨‍🎤, or relax💤 in our inviting living area after a day of exploring. The fully equipped kitchen allows for easy meals at home, or savor local cuisine minutes away. Perfect for solo travelers or couples seeking a memorable stay in the heart of KC!

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.

Two-Bed - Top Floor - Pet-friendly/Good Parking

Enjoy this bright, spacious, amenity-packed suite just minutes from The Plaza, Westport, Crossroads, and Downtown. This second floor suite has a parking area behind the house. It's best for cars and smaller SUVs, but most trucks and SUVs can get by also. This guest suite on the upper floor offers a king and twin bed, large bathroom, and sitting room with a breakfast nook. Guests are provided special amenities such as a bidet, toaster oven, mini fridge, electric kettle, and ice maker.

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!

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 3 Bedrooms 2 Bath House 4 Beds Sleeps 8

This charming 3-bedroom, 2-full bathroom house offers a perfect blend of comfort and convenience. Access to a one car garage. Bedroom 1: King bed Bedroom 2: Two Full beds Bedroom 3: Queen Bed Central location in Kansas City. Easy access to all main attractions Kansas City has to offer. No Pets *12 minutes: Downtown/Power & Light District. *10 minutes: Westport/Plaza. *15 minutes: Legends/Sporting KC. *20 minutes: Kauffman Stadium/Arrowhead. *15 minutes: KC Current Stadium.

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

Minimalist Modern Strawberry Hill Get-Away Home

Entire, separate entry, second floor studio. Minimalist modern decor, nice clean small space with everything you need. We aim to have your stay be an enjoyable experience, greeting you with a clean home, ensuring you have what you need during the stay, and being available as needed. Approximately 5-10 from downtown KCMO, Power and Light, City Market. Within walking distance of a few local family owned restaurants and bars.

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.