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.

Charming West Plaza House 2 bed/2 bath

Welcome! This historic Bungalow in the West Plaza Antique District is newly updated inside and out. The home was originally built in 1901 and boasts authentic charm with modern day amenities. This 2 bed, 2 bath (2 master suites) home sits on a quaint street just west of the renowned Country Club Plaza. It can accommodate up to 5 guests in beds with an air mattress available for an additional 2. (additional fee). This house has a private driveway, front porch and fenced backyard with gas grill.

FIFA Ready! Visit KC! Prime location

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!

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

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.

Skyline | Hot tub | Rooftop Patio | Amazing Views

Hot tub, fire pit, rooftop patio and amazing views of the KC Skyline! Brand new home, with comfortable king size beds, 3 tv's and modern decor. Outdoor grill, picnic table, wood fire pit and rooftop gas fire pit. Hammocks, corn hole and board games. After booking, guests are required to complete a renter’s agreement and provide a valid government-issued photo ID prior to check-in. This is required for all guests without exception.

WestSide Brick Barn Studio

The Brick Barn Studio is a sweet and peaceful private space on the first floor of a late 19th century Carriage House. Guests enjoy private entry to their accommodation, mini kitchen, shower/bathroom, and laundry, king mattress on a unique built-in bench platform, and a convertible sofa for another guest or two. There is a privacy curtain provided for guests who would like a little separation between the bed and sleeper sofa.

Luxury 3 br Sleep 7 <20 min to Soccer Stadium

Soccer/Football Fans! 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. ⭑CONTACT US FOR SEASONAL DISCOUNTS⭑ ⚽️⚽️ WELCOME TO KANSAS CITY WORLD CUP 2026 TEAMS & TICKET HOLDERS ⚽️⚽️

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

Rosedale Hills Stone Villa #1

Take it easy at this unique and tranquil getaway. Our famous Rosedale Hills Stone Villa has over 100 years of history. Come and stay with modern amenities inside an old stone exterior from many years gone by to relax and enjoy your stay in Kansas City.