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

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.

Cozy Charming Cottage 3b 2bath firepit near Plaza

Nothing says home sweet home like this Cozy Charming Kansas City Cottage. 3 bedroom, 2 bath home, screened in porch, fenced in backyard, tree-lined quiet street, and full kitchen. Enjoy a short walk to our local coffee shops Hi Hat & Front Range, Joe’s BBQ, Rainy Day Books, grocery, parks, and restaurants. Centrally located so you can explore the very best KC has to offer- Chiefs, Royals, Soccer, Country Club Plaza, Westport, Union Station, TMobile, Crown Center, Power & Light, and museums!

Cozy Queen Studio- Perfect for Your KC 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.

Peaceful Retreat - 20 Minutes to Almost Anywhere!

Put your mind at ease in this perfectly tucked away home located in a quiet suburban neighborhood. Perfect for anyone who wants to be close to attractions or the hospitals without all the noise of the city. ✫ 2 min >> St. Luke's ✫ 10 min >> KU Medical Center ✫ 6 min walk >> New Park ✫ 20 min walk or 3 min drive >> downtown l ✫ 10 min >> Plaza & Westport ✫ 3 min >> Walmart & the grocery store ✫ Quick highway access! ✫There is a separate unit in the basement. No shared spaces!!!

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!

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.

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.

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.