Holiday rentals in Waldo

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.

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.

Crown House- Cozy 3BR * King Bed* Walking Trail

Your family will be close to everything when you stay at this thoughtfully remodeled 100-year-old home, which has the unique distinction of hosting 2-time Super Bowl champion and KC Chiefs safety, Justin Reid. Walk or bike along the Trolley Trail to the finest Waldo and Brookside attractions. You are only: 9 minutes drive from the National Toy Museum, UMKC, Loose Park 14 minutes drive from the Plaza, Nelson Atkins Museum of Art 19 minutes drive from Crown Center, WWI Museum & Union Station

King Bed Master Close to Everything! Fiber Wi-Fi

Enjoy Kansas City! The City's PennHouse in Waldo is a modern 1200 sqft. 3 bedroom 2.5 bath home with private driveway and large backyard. It includes WiFi, Smart TV's, and fine furniture. Within walking distance is endless dining from dives to white table cloth. One block away is the historic Trolley Trail for walking, running and biking. Perfect for the business executive, busy traveling family, couples, or single traveler looking for space and amenities. Pet friendly with additional fee.

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.

Wonderful Waldo Bungalow

Darling bungalow recently remodeled/updated. Very quiet street 3 blocks off Wornall Rd. 1 mi. from Ward Pkwy Center - shops/restaurants/theater. 3 mi. to Brookside, 5 mi. to Plaza. Lg fenced backyard. Carport. Coffee, toiletries, new sheets and towels for your enjoyment. We love this home and believe you will find your stay enjoyable. Home was built in the 50's and has all the charm you would expect! If traveling with pets, the must be pre-approved and pet cleaning fee agreed upon.

Private Penthouse +Balcony Overlooking 39th Street

Located atop the Meshuggah Bagels along the iconic West 39th Street, this renovated 3rd level flat is truly an urban oasis. Guests are treated to comfortable accommodations with private access to your own balcony overlooking 39th Street! Get a glimpse of Kansas City through the eyes of a local! Be sure to check out the virtual guide book full of local restaurants, shops, and nightlife. There’s something for everyone. From global cuisine to barbecue, shopping and more!

Cozy KC Carriage House

Unique former carriage house located in the charming Waldo neighborhood of Kansas City. Great location a short drive to the Country Club Plaza, Arrowhead & Kaufman Stadiums, Power & Light, Crossroads and Downtown KC as well as Leawood, Prairie Village and Overland Park. Kansas City Registration No. NSD-STR-01359. Always ask for the short term rental registration so your stay isn't cut short with a compliance eviction by city enforcement.

Cozy studio: inviting, work-and-play neighborhood

Small, private studio complete with laundry, kitchenette, outdoor space and more! Located in the amenable South Plaza neighborhood, you will be just steps away from the Plaza shopping district, University of Missouri-Kansas City, Whole Foods supermarket, Loose Park, and other attractions. Others, such as the Nelson-Atkins Museum of Art and Union Station are just a few minutes away by car or easily-accessible public transportation.

Chateau Waldo - Cuddle-up Charming Home

Now booking for the World Cup! Our home is just 15 minutes from the soccer stadium!! Come stay at our charming updated Waldo retreat located in the heart of Kansas City! As a young couple starting out, my wife and I renovated this sweet home and made it beautiful. This lovely two-bedroom house features a remodeled kitchen and bathroom, office space, and a custom built screened in outdoor back patio. KC License # NSD-STR-00929

Charming Waldo Reader's Retreat

Sweet little bungalow in the heart of Waldo. Sits at the back of the property, so there is no fenced in yard. We had a new driveway poured in 2025, you’re welcome to use that or park on the street. Main bedroom is on the ground floor with an additional bed upstairs (the stairs are ladder-like, so not suitable for everyone!). We love this little house so much and think you will too.

Cozy Cottage in Waldo

Charming two bedroom, one bathroom house in the heart of Waldo. Within walking distance of the KC Bier Company Brewery and the popular Trolley Track trail. This house is located 5 minutes from Brookside, 10 minutes from the Plaza, and around 20 minutes to downtown KC. We have a fully-stocked kitchen with a Keurig, smart TV’s in both rooms, and a front screened-in sunroom.