Holiday rentals in Waldo

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.

Value · Location · Kitchen

The Black Walnut KC Pool House & Hot Tub

Beautiful pool house that sleeps up to 5 with two amazing king size beds, a queen pull out couch, and twin bed along with a beautiful full bathroom, kitchenette, laundry, and bar! Custom artificial turf, heated pool, and hot tub that are open year round make this a unique resort style stay in the heart of the favorite neighborhood of all of Kansas City - Brookside! We do not do parties or events, but love your furry family! @theblackwalnutkc Perfect for couples, families or friendscations!

Family · Location · Check-in

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.

Family · Location · Wifi

Private Retreat in Walkable Waldo Neighborhood

✔ Free Parking ✔ Laundry ✔ 10–15 min to Plaza / Downtown ✔ 20 min to Stadiums ✔ Fast WiFi ✔ Quiet neighborhood Private home in the wonderful 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 Superhosts. No big unreachable property manager or out of town owners. No chatbots, no online request forms and no endless automated phone menus.

Value · Family · Check-in

Trendy Mid-Century Bungalow

Enjoy the beautiful light, charm, and character of our cozy Waldo bungalow, located on a quiet, safe residential street just 15 minutes from downtown Kansas City. The home fetures a sweet screened porch, a fully fenced yard, and a shared garage. You’ll be within walking distance of great restaurants, coffee shops, and bars, with a biking and walking trail right across the street. The house has great WiFi and is well maintained. We hope you love Kansas City and our home as much as we do!

Value · Location · TV

BKS Carriage House: Exciting French Modern Fun

Nestled in Brookside (BKS), our 2-bedroom retreat, featured on 'Bargain Mansions' (season 5, episode 6), blends French charm with modern comfort. Conveniently near the Brookside shops, the Plaza, Waldo, and downtown, it exudes timeless elegance. Enjoy included pastries and drinks, a quaint breakfast nook, and dedicated kids' space. We also offer complimentary beverages and use of picnic basket for your stay. Immerse yourself in Brookside's charm - secure your booking today!

Value · Family · Kitchen

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!

Value · Family · Comfort

Family Friendly Historic Waldo Home

Welcome to your home away from home in the heart of Kansas City’s beloved Waldo neighborhood! This spacious 4-bedroom, 2.5-bathroom home offers the perfect blend of historic charm and modern comfort. Whether you're visiting for a Chiefs game or exploring the Country Club Plaza, or simply grabbing a slice at Waldo Pizza and strolling the Trolley Trail, our home serves as the ultimate base camp for families, groups, and traveling professionals.

Value · Location · Getting around

Brookside 4BR | Easy Arrowhead Access | Sleeps 8

Welcome to Mod Cottage, a beautifully preserved 1936 Brookside home where groups can spread out, reconnect, and feel taken care of. Stay in one of KC's most loved neighborhoods, with easy access to GEHA Field at Arrowhead Stadium, the Plaza, museums, restaurants and downtown. Four bedrooms, three baths and multiple gathering spaces make the house especially comfortable for families, friends and groups visiting Kansas City together.

Location · Family · Amenities

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

Family · Location · Long stay

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.

Family · Location · Heating

Wonderful Waldo Bungalow

Recently updated. 8 miles to Arrowhead Stadium. Quiet street, 3 blocks off Wornall Rd. 1 mi. from Ward Pkwy Cntr shops/restaurants/movie theater. 3 mi. to Brookside, 5 mi. to Plaza . Lg fenced backyard. We love this home and believe you will find your stay enjoyable. Home was built in 1950's and has all the charm you would expect! Pets must be pre-approved. $50 Pet fee applies.

Value · Location · Walkability