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 Southmoreland
4.99 out of 5 average rating, 119 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 Westwood
4.99 out of 5 average rating, 685 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 Mission
4.93 out of 5 average rating, 393 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.

Guest favourite
A cozy living area is highlighted by a large wall mural featuring trees and soft light. A sectional sofa and an armchair provide comfortable seating. A small coffee table sits on a patterned area rug, while a television and a work desk are positioned nearby.
Home in Overland Park
4.94 out of 5 average rating, 551 reviews

Convenient Overland Park cottage on quiet street

Come relax in this 2 bed/2 bath cottage and enjoy the privacy of an 800 sq foot single family home. Master has queen bed and it's own private bath. 2nd bedroom has a queen bed. A queen size aerobed mattress is provided for extra sleeping room. Has a 50" flat screen TV equipped with Netflix/DVD player. Kitchen has granite counters and is fully stocked to make any great meal. Dining table seats 4 and kitchen seats another 3. Backyard with fire-pit. Pets welcome. Yard is only partially fenced.

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 Mission
4.98 out of 5 average rating, 100 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 Roeland Park
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 Roeland Park
4.89 out of 5 average rating, 349 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 Fairway
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.

Superhost
A bright living area features a comfortable sofa paired with an armchair. A small coffee table sits at the center, adorned with flowers. Large windows allow natural light to fill the space, showcasing a dining area with a modern table and chairs against a neutral wall.
Home in Mission
4.87 out of 5 average rating, 144 reviews

Mission Getaway,King Bed, Game Room

20 minutes from Arrowhead Stadium – a perfect stay for FIFA World Cup Kansas City 2026. This cozy, newly renovated 4-bedroom home sleeps up to 8 with 1 King, 2 Full, and 2 Twin beds. Enjoy two living spaces, a pool table and foosball, full kitchen with new appliances, and free parking. Walk to great Kansas City restaurants or relax at home with family and friends. Ideal for World Cup visitors, business travelers, couples, and small groups exploring KC.

Top Guest favourite
A modern farmhouse is showcased with a well-maintained lawn and surrounding trees. The exterior features a classic white facade, black shutters, and a welcoming front porch with multiple rocking chairs, inviting a sense of relaxation.
Home in Shawnee
4.99 out of 5 average rating, 108 reviews

Beautiful and Spacious 1908 Modern Farmhouse

Just 17 miles from Arrowhead stadium, this charming modern farmhouse offers over 1,800 sq. ft. of space with the entire home to yourself. Enjoy a private driveway with ample parking, a spacious family room with a 75-inch TV, and an open kitchen and dining area perfect for gathering. Relax with morning coffee on the front porch or back patio, and unwind knowing every bedroom has a smart TV, plus a work desk and queen sleeper sofa on the main level.

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 Roeland Park
4.94 out of 5 average rating, 108 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