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

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.

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.

Remodeled Home Close to KU Med w/ Off Strt Parking

Updated home situated in a great close-in neighborhood that's perfect for exploring KC. Enjoy this elegant home that has been recently remodeled & retrofitted with all of today's amenities. Walk to KU Med Hospital & all the restaurants, shops & bars on 39th Street. Westport & the country club plaza are one mile away. The Cross Roads District & Downtown KC (Sprint Center, Power & Light, The Midland Theater, etc) are all a quick 5 minute ride. Arrowhead & Kauffman Stadiums are 15 minutes away.

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.

Mins to downtown! Perfect Kansas City Getaway!

Cozy 1-Queen Bedroom Studio in a Peaceful Neighborhood – Perfect for Your KC Getaway! Escape to this charming, ground-floor studio located in a serene, well-established neighborhood—an ideal retreat for both business and leisure travelers. This cozy 1-bedroom, 1-bathroom unit is designed for comfort and convenience, featuring a washer and dryer and one assigned parking spot right at your doorstep. Our studio is pet-friendly, so you can bring your pet along to enjoy your stay in KC.

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.

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.