Family-friendly holiday rentals in Prairie Village

Luxury Retreat 1 block to downtown OP

Looking for better than average? Designed as a comfortable, relaxing, model smart home with the latest features. For the perfectionist that seeks a better stay for work, play or relaxing. Eating healthy? Masticating Juicer, & Ninja. Coffee? French Press, Coffee Grinder, Nespresso, & Keurig. Clean, comfortable, peaceful and one block to downtown Overland Park. Gel, memory foam mattress. Low profile shower w/ handheld. Grout free, clean, Onyx shower. HVAC has UV, Ozone & bio-scrubber. Outdoor pa

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

Spacious Luxury Retreat w/ Hot Tub & Movie Theatre

Relax and take a break in this spacious family retreat! Check out the great outdoor space with 8-person hot tub, firepit and quite patio. Relax inside on the 12' sectional and watch your favorite movie on a 150" screen! Little kids will love swinging on the back yard playset, or climbing on the 25' pirate ship and two-story castle! Pool table in the game room is great for all ages! All bedrooms feature plush bedding and high quality mattresses and smart TVs. Full kitchen cutlery and utensils.

Private Retreat in Walkable Waldo Neighborhood

✔ Private detached home ✔ Free Parking ✔ Laundry Included ✔ 10–15 min to Plaza / Downtown ✔ Fast WiFi ✔ Quiet neighborhood Unique Carriage House in the Waldo neighborhood of KC a short drive to the streetcar, Plaza, Stadiums, Power & Light, Crossroads and Downtown as well as Leawood, Prairie Village and Overland Park. Highly rated, highly trusted local host. Always ask for the short term rental registration number so your stay isn't cut short with a compliance eviction by city enforcement.

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!

Top-Rated 4BR/Private Pool/Patio Perfect 4 Groups

World Cup oasis -4-bedroom home with heated private pool, ideal for families and professionals. Comfortably sleeps up to 10 guests and is a great home base for out-of-town visitors attending World Cup matches or watching the games during downtime. Located in a desirable neighborhood close to dining, shopping, and golf. Features 4 bedrooms (2 en suite), 3.5 baths, a fully equipped kitchen, large laundry room, and two living spaces. Pool open April–late Sept/early Oct, weather permitting.

Modern Prairie Village Home

Nestled in the heart of Prairie Village, this delightful home was recently remodeled and is equipped with everything you need for the perfect stay. Enjoy luxury mattresses in the two bedrooms which are both equipped with TVs. Cozy up next to the fireplace with your favorite book or watch a movie on the living room tv. Play a round of foosball or shuffle board with the game on while your favorite dish is smoking in the Traeger outside. Walk to the Shops of Prairie Village within minutes.

Prairie Village Modern Farmhouse! Great Location!

Enjoy your home away from home with style! This separate guest house has 1 bedroom & 1 bathroom that gives you privacy while still being centrally located in Prairie Village of Kansas City. Floor to ceiling shiplap walls, wood floors, black metal railing, & stylish decor you will feel like you're in an episode of Chip and Joanna Gaines' Fixer Upper! The home has its own private entrance, Washer/Dryer in unit and a fully functioning kitchen. High speed GooglFiber internet.

The Waldo Walkabout - Pet Friendly + Fenced Yard

🏡 Waldo Walkabout – Your cozy KC bungalow! 🛏 2 Queen bedrooms with Smart TVs 🛁 1 spa-like bathroom with luxury Tommy Bahama products 🍳 Fully stocked kitchen + coffee bar (Keurig, French press, pour-over) 🛋️ Living room with plush sectional & 55" Smart TV 🍽️ Dining table for 6 + mixology set 🌳 Fully fenced backyard & shaded deck 🐾 Pet-friendly with secure yard 🚗 Private driveway & street parking in vibrant Waldo neighborhood

Pink Spot w/ Hot Tub, Game Room + Crazy Bunk Bed!

❤️ Welcome to this one-of-a-kind three-bedroom home nestled in a peaceful and secure neighborhood just off I-35. With a range of unique amenities, it’s the ideal place for you and your group or family to relax, unwind, and create unforgettable memories together. Hot Tub, Mini Golf, Bowling, Game Room, Bunk Bed with Slide, Fire Pit, Arcades, Pool Table, Shuffleboard, Board Games and many more - you'll never want to leave! ❤️

Cozy Prairie Village Home for World Cup Fans

Coming for the World Cup? This home is available and ideal for groups needing a home base for the entirety of the tournament! -65” Smart TV w/streaming services and local channels -High Speed Wifi -17 min drive to downtown Kansas City -22 min drive to GEHA Arrowhead Stadium -30 min drive to the airport (MCI) **Effective November 1, 2025** Midterm rental available, 30 days or more! Lawn care included!