Family-friendly holiday rentals in Leawood

Where's Waldo? - Garage Loft

This tiny loft apartment is located in an old neighborhood with big trees, and just a short walk away from Waldo shops, restaurants and bars. Easy travel to Westport, Country Club Plaza, Crossroads, River Market, Power & Light, and many more super fun KC gems. The apartment is in the space that once was our old garage, so it's attached to our home. You have a separate and private entrance, full bath with an amazing shower, a small kitchen with appliances, and a loft bedroom with ladder access.

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.

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!

Truman Loft

Truly one of a kind Historic property converted into a spacious, cozy loft in the heart of South KC. This 100-year-old space(5 min from HS Truman farm. He spoke on this stage on his first political campaign) has been completely rennovated with concrete countertops, beautifully vaulted ceilings, huge bathroom, built in workspace and even a fun kid's room. Let the natural light pour through the massive windows or close the curtains and dim the lights:) We hope you enjoy it as much as us!

modern x charming 1930s farmhouse! 10 min plaza!

Step into our fully renovated 1930s farmhouse and be welcomed by natural light and an inviting open concept. The kitchen features beautiful marble countertops and all the essentials. Relax in the stunning black freestanding bathtub or dine al fresco on the spacious outdoor patio. With three cozy bedrooms, including two queen-size beds and one full-size bed, this home can accommodate up to six guests. Experience the perfect blend of old-world charm and modern convenience during your stay.

Studio Guest House

Enjoy Southern OP in this quiet neighborhood. Our studio guesthouse has a full kitchen, TV, a new a/c/heater, and google fiber internet. In case you get lonely, we have 2 friendly dogs always looking for attention. We are about 45 minutes away from the Kansas City airport, Kauffman Stadium, Arrowhead Stadium, the KU main campus, and the Harry S Truman sports complex. We are 10-15 minutes from the Scheels soccer complex. Overland Park has plenty of Kansas barbecue and shopping.

The Sunnyside- Waldo Ranch + Fenced Yard + Parking

🌞 Prime location across from Sunnyside Park in historic Waldo 🌞 Stylish 2-bedroom home with Queen beds 🌞 1 full bathroom with luxury Tommy Bahama bath products 🌞 Fully equipped kitchen w/ oversized granite island & coffee bar 🌞 Open living & dining area with Smart TV + board games 🌞 Private backyard + fenced dog-friendly space 🌞 Washer/dryer in basement 🌞 Driveway parking + high-speed WiFi 🌞 Steps from local shops, cafes, restaurants & Trolley Trail

Charming Basement Oasis

Pets- Dogs Only. Private basement suite with walk out entry, situated 1 mile from Historical Downtown Overland District. Within walking distance to South Lake Park. Basement suite is part of a single family home. The house is central air with thermostat located upstairs. Main level is occupied by residents & is separate from the basement suite. Suite includes full kitchen & laundry, full bathroom, walk in closet, one queen bed, & fold down sofa.

Spacious Home With 2LivingSpaces|Fenced Yard+Pets

The best of what KC has to offer-in a newly renovated home located in one of the most coveted residential neighborhood. Just a few walks away to best restaurants, coffee shops and grocery store and a few miles from the interstate and downtown, yet situated in a quiet, spacious, and safe alcove. All newly remodeled with stainless steel appliances, granite countertop and finished with quality furnishings.

Vine & Petal - A Cottage Retreat

IG Handle: @vine_and_petal Ready to escape the hustle and bustle of the city without compromising on amenities? Join us at the Vine & Petal cottage retreat where we invite you to relax and unwind. We are conveniently located 3 minutes from I-435, 8 minutes from I-70, and 10 minutes from Legends Shopping Center including the Kansas Speedway and Sporting KC. Photographers send inquiries only.

Floyd's Retreat Stylish Home | Walk to Downtown Ov

Professionally designed 2-bedroom retreat just one block from vibrant downtown Overland Park! This stylish home comfortably sleeps 4 and is perfect for families, couples, or business travelers. Enjoy two living areas, a fully equipped kitchen, and a dedicated workspace. Walk to local shops, restaurants, and bars from this convenient and welcoming home base.

~Spacious Home in Family Friendly Neighborhood~

Enjoy this beautifully updated Home Away From Home centrally located to everything Kansas City has to offer with quick and easy self Check-in. Located just 5 minutes between downtown Overland Park and Prairie Village Shoppes, you will be close to everything while also being nestled into a very quaint and peaceful neighborhood. The best of both worlds!