Holiday houses in Roeland Park

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Top-rated holiday rentals in Roeland Park

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Top Guest favourite
A dining area is highlighted by a round wooden table surrounded by four gray chairs. Floating shelves are adorned with books and decorative items. A large potted plant adds a touch of greenery, while a decorative mirror reflects light and space.
Home in Kansas City
4.99 out of 5 average rating, 125 reviews

Coveted Museum District Stylish Eastlake Victorian

Step into this exquisitely renovated Eastlake Victorian on tranquil Oak St, in Kansas City’s vibrant Southmoreland, steps from Nelson-Atkins, KCAI, Plaza, and Westport. This 3-bed, 2-bath gem boasts soaring ceilings, floating cedar shelves, and a private backyard patio for serene retreats. Enjoy designated parking and a walkable Museum District, just 4 blocks from the Main Street. Blending historic elegance with modern flair, this chic haven promises an unforgettable stay in KC’s cultural heart.

Top Guest favourite
A spacious sleeping area features a queen-size bed dressed in a turquoise coverlet, complemented by decorative pillows. Natural light floods through a nearby window covered with light curtains. A wooden dresser and bedside table add warmth to the room, while framed artwork enhances the decor.
Guesthouse in Shawnee Mission
4.99 out of 5 average rating, 690 reviews

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.

Top Guest favourite
A spacious sleeping area features a queen-size bed dressed in soft linens and a blue sofa, along with a coffee table. A smart TV is mounted on the wall, and a desk is positioned in the adjacent office area, illuminated by natural light from nearby windows.
Home in Shawnee Mission
4.93 out of 5 average rating, 394 reviews

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

Guest favourite
A spacious living area is defined by dark walls and hardwood flooring. A large white sectional sofa and a sleek coffee table are positioned in front of a white stone fireplace. Natural light floods the room through large windows, enhancing the inviting ambiance.
Home in Mission
4.92 out of 5 average rating, 145 reviews

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.

Top Guest favourite
A bright living room features dark hardwood floors and comfortable seating arrangements, including two deep gray sofas and a round coffee table. Natural light filters through the blinds of a large window, while decorative plants add a touch of greenery to the space.
Home in Merriam
4.98 out of 5 average rating, 105 reviews

Comfy Hideaway in Merriam

This beautiful home is located in a quiet and peaceful neighborhood in Merriam, KS, yet only minutes away from downtown KC and the Country Club Plaza. Conveniently situated near parks, shopping, and dining, this place is your perfect base to explore the vibrant Kansas City area. Ideal for families, friends, or solo travelers seeking a relaxing place to stay. The home features modern amenities, cozy furnishings, and a fully equipped kitchen. We warmly welcome people of all backgrounds.

Guest favourite
A bright and welcoming room features a cozy bed with plush pillows and decorative throw blankets. Two bedside lamps provide soft lighting beside the bed. Neutral walls and flooring create a calm atmosphere, while a ceiling fan offers a gentle breeze.
Home in Shawnee Mission
4.83 out of 5 average rating, 102 reviews

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

Top Guest favourite
A modern kitchen features wooden cabinetry and a dark countertop. Stainless steel appliances include a refrigerator and a stove. Open shelving displays dishes and containers, while a sink is positioned beneath a window. Seating includes red bar stools and a dining table nearby.
Home in Shawnee Mission
4.89 out of 5 average rating, 350 reviews

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

Top Guest favourite
A charming home is set within a lush lawn, framed by vibrant flowering plants and two decorative urns. The entryway features a large front door with a modern light fixture above. A cozy bench is positioned beside the door, inviting relaxation.
Home in Shawnee Mission
4.96 out of 5 average rating, 109 reviews

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.

Guest favourite
A comfortable living area is showcased, featuring a leather sofa and two armchairs arranged around a round coffee table. Light hardwood floors complement a large area rug, while natural light enters through the windows. A full-length mirror adds depth to the space.
Home in Merriam
4.91 out of 5 average rating, 190 reviews

Cheerful 3 bedroom fully renovated cottage home

The Hadley cottage is a great place to bring the family for a fun get-a-way or perfect for your work needs. This chic & modern cottage is 3 minutes from I-35 and conveniently located to get you anywhere in the KC metro quickly. This is a quiet neighborhood with wide sidewalks within walking distance to restaurants or shopping. The cottage features a renovated interior in 2022, huge fenced backyard, and a long driveway for ample parking.

Guest favourite
A bright living area features a modern couch adorned with colorful cushions. A small chair and table occupy one corner, and large windows provide natural light, offering views outside. A patterned area rug adds warmth to the space, enhancing the minimalist decor.
Home in Kansas City
4.95 out of 5 average rating, 1,017 reviews

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.

Top Guest favourite
A modern living area features a stylish light-colored sofa and a green accent chair, arranged around a circular coffee table. Floor-to-ceiling windows provide ample natural light and views of the surrounding greenery. A wooden accent wall and sleek television add to the contemporary design.
Home in Kansas City
4.98 out of 5 average rating, 250 reviews

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 ⚽️⚽️

Guest favourite
A cozy living area is presented with a gray sofa adorned with decorative pillows. A round coffee table made of wood is centered on an area rug featuring a muted pattern. A light fixture and wall decor enhance the space, while the front door is visible in the background.
Townhouse in Shawnee Mission
4.94 out of 5 average rating, 109 reviews

Mins to downtown- 2 beds/1 bth- your KC getaway!

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.

Popular amenities for Roeland Park holiday rentals

  1. Airbnb
  2. United States
  3. Kansas
  4. Johnson County
  5. Roeland Park