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

Cozy Charming Cottage 3b 2bath Fire Pit

Ideal World Cup Stay! Central, comfy, and convenient, Cozy Kansas City Cottage. 3 bedroom, 2 bath home, screened in porch, fenced in backyard, tree-lined street, full kitchen, safe neighborhood! Walking distance to the famous Joe’s BBQ, local coffee shops Hi Hat & Front Range, Rainy Day Books, grocery, parks, and restaurants. Centrally located so you can explore all KC World Cup activities, Royals, Country Club Plaza, Westport, Union Station, TMobile, Crown Center, Power & Light, and museums!

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!

Modern Urban Oasis with Fire Pit 3br Sleeps 7

Welcome to your modern urban retreat located in Kansas City's vibrant Rosedale neighborhood. This 2 bedroom plus loft (sleeps 7) and 2.5 bathroom home is designed to provide you with luxurious comfort and eco-friendly style, making your stay truly exceptional. Centrally located, close to the vibrant 39th street shops and restaurants, KU Medical Center, Downtown Kansas City, The Country Club Plaza, Westport and the KC Power & Light District. ⭑CONTACT US FOR SEASONAL DISCOUNTS⭑

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.

Peaceful Retreat - 20 Minutes to Almost Anywhere!

Perfectly tucked-away home in a quiet suburban neighborhood—an ideal base for World Cup travelers who want quick access to matches, fan zones, and downtown Kansas City without the noise. Enjoy a peaceful stay with easy highway access. ★ 10 min > KU Medical Center ★ 6 min walk > New Park ★ 20 min walk or 3 min drive > Downtown KC ★ 10 min > Plaza & Westport ★ 3 min > Walmart & grocery store ★ Quick highway access to stadium routes ★ Separate basement unit — 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!

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.

Visit Kansas City! Prime location!

Cozy 2-Queen Bedroom Unit in a Peaceful Neighborhood – Perfect for Your KC Getaway! Welcome to our charming, private top-unit townhouse, nestled in a friendly, well-established neighborhood. This 2-bedroom, 1-bathroom unit offers the ideal space for a relaxing stay, complete with two assigned parking spots for your convenience. Guests must be able to use stairs to access the unit.

The Checkmate - Roeland Park Ranch + Pet Friendly!

🏡 Charming Roeland Park 2-bedroom ranch (1 King, 1 Queen + Queen daybed) 🛁 1 full bathroom with luxury Tommy Bahama products ☕ Fully equipped kitchen with upgraded coffee bar 🛋 Cozy living room with Smart TV + board games 📶 High-speed WiFi, USB charging stations 🌳 Private deck, pet-friendly, driveway parking 📍 Minutes from Country Club Plaza, Downtown KC, local shops & parks