Family-friendly vacation rentals in Chesterfield

Pacific Palace, super unique!

The Pacific Palace is unlike any other Airbnb! Located in the heart of downtown Pacific, Missouri - only 2 minutes from Highway 44 and 10 minutes from Purina. This house is an incredible one of a kind treasure with lots of unique features including: outdoor gazebo, fish pond, all original cedar interior design, two second story balconies, two large bat tubs (one located in the main bedroom) and so much more!!! Private parking and a gate for added privacy. Just minutes from Six Flags. Book today

Family · Indoor spaces · Long stay

Getaway House | St Charles 4BR Sleeps 11 Game Room

DUE TO DEMAND - MUST READ: Starting August 31st, we're adding a second master ensuite - king bed, private full bath - and expanding the game room by 500 sq ft to a full 900 sq ft of pure entertainment: pool, arcade, and a big screen. We're closed September and October to build it, then reopening November 1st, completely brand new. All of our fall and winter dates are open right now, and holiday weekends at a house this size always go very quickly, so book yours before somebody else grabs them.

Kitchen · Family · Value

Family/4bd/2bth/Huge Yard/Playset/Ping-Pong/Arcade

Our freshly updated and furnished house is ready for the family with kids, the adult getaway, and wedding parties from Stone House event venue across the street! Boasting tons of privacy, a huge yard with a playset and games, a fully stocked kitchen with everything you could want for a Thanksgiving dinner, and a large basement with arcade boxes, ping pong, weights, and seating areas. A very safe and secluded location that is close to amazing parks, restaurants, wineries, and shopping.

Indoor spaces · Kitchen · Value

*NEW HotTub* The Jewel on 5th-2br2b-near Main

A true gem only a 15 min drive from the STL Airport. Enjoy a well equipped, century home a short 12 min walk to Historic Main and a HOTTUB. The large stocked kitchen is great for entertaining. Master bedroom w/luxurious, king sized, 4 poster bed and ensuite bathroom awaits you. In the private, queen suite you’ll find its own bathroom and another door leading onto the deck. The chair off the kitchen folds out to a standard twin and bedding is provided for the sofa as well. Can sleep 6.

Kitchen · Indoor spaces · Nearby

The HIPPO House! All 1950s Mini-Golf! MCM Lustron

Welcome to a unique 3-bedroom Lustron home in St. Louis, where retro charm and quirky details await! Greeted by Chelsea, our giant pink hippo, every guest steps into a rare mid-century gem—one of only 1,200 remaining Lustrons and even rarer with three bedrooms. Iconic steel walls, built-in cabinetry, and 1955 decor immerse you in history, while Wi-Fi ensures comfort. A backyard 9-hole mini-golf course adds some family fun. Book today to enjoy Chelsea’s welcome and a slice of history!

Family · Indoor spaces · TV

Cottage on Main Street- Low Cleaning Fee

MESSAGE FOR SHORT STAY DISCOUNT Stay in the heart of Historic Downtown St. Charles! WALK EVERYWHERE at this beautifully updated 2BR/1BA blends modern comfort with charm just steps from Main Street. Walk to award-winning restaurants, unique boutiques, coffee shops, festivals, and riverfront views. Directly across from the Katy Trail, perfect for biking and morning strolls. Minutes to Ameristar Casino and 12 minutes to STL Airport. Fast Wi-Fi, cozy beds, and an unbeatable location.

Indoor spaces · Kitchen · Shared spaces

Private 3-Acre Retreat • Koi Pond & Waterfall

Escape to Rick’s Retreat, a private 3+ acre wooded getaway in Wildwood, MO. Enjoy a beautiful koi pond and waterfall, wraparound deck, fire pit, grill, pool table, and spacious timber-frame home. With 4 bedrooms, 5 beds, and room for up to 9 guests, there’s plenty of space to relax and reconnect. Babler State Park is just 1 mile away, with Chesterfield Valley, restaurants, shopping, and St. Louis attractions a short drive away. Perfect for families, friends, and weekend getaways!

Kitchen · Indoor spaces · Hospitality

Spacious 6BR Retreat | Near I-64 & Weddings

Enjoy a comfortable stay in this modern smart home near Highway 64, ideal for families, groups, and guests attending nearby weddings. Cook in a fully equipped gourmet kitchen, enjoy eight 4K smart TVs, reliable WiFi, and a dedicated workspace for remote work, all enhanced by smart technology for added comfort and ease. Conveniently located near dining, shopping, and popular attractions, and just 30 minutes from STL Airport, it offers a smooth, spacious, and inviting stay.

Kitchen · Indoor spaces · Check-in

Spacious Home - Heated Pool Open Until November

Heated Pool is Open through end of October! Exceptionally updated sprawling home w/ 2400 sqft of living space inside with multiple entertainment areas and rooms well spread out. This is the perfect house for multiple families or generations to enjoy together! The house is amenity packed and offers a stunning kitchen, large backyard, pool house/detached office, and plenty of privacy! Located in the perfect central location within 5-15 minutes of the cities main attractions!

Kitchen · Family · Long stay

Blair's Jungle House w/ Hot Tub - Game Room

Welcome to Blairs Jungle House in St. Peter's, MO. Bring the family, plenty of room to spread out and relax. Newly renovated 4 Bed 3 full Bath with Game Room in LL & Hot Tub! Please come and enjoy your stay. Kitchen is fully stocked with all the essentials for casual cooking or thanksgiving dinner. Whether you're in the mood to relax or hang out in the Game Room, Blair's House has you covered. Close I-70 & 364 Check out our profile for more listings.

Kitchen · Family · Check-in

Hot Tub Gazebo | Game Room | 2 Kings | Sleeps 8

A spacious, fully stocked home with a hot tub beneath a private covered gazebo, a fire pit, a lower level game room, and a big fenced backyard. Send the kids downstairs to the arcade and indoor swing while the adults soak under the gazebo, or make it home base for a wedding at nearby Stone House. Two king beds, a bunk room kids love, and a kitchen ready for real cooking, all in a quiet St. Charles neighborhood near restaurants, wineries, and parks. Sleeps 8.

Indoor spaces · Kitchen · Access

Great Location Fam Friendly Home w/Lrg Fenced Yard

Newly finished basement with 4th bedroom (King bed), large play/relaxation space & large 120-inch projector screen and separate large speaker for movie nights! Beds are all brand new comfortable memory foam! This house is in such a great and convenient area! Freshly renovated with all brand new beds and furniture, a fully stocked kitchen for cooking and baking and a fenced in pet friendly backyard! TONS of kids and baby items!

Kitchen · Family · Comfort