
Family-friendly holiday rentals in Chesterfield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chesterfield
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

3 bedrooms with hot tub, fireplace. Walk to town.
We enjoyed our stay and plan to stay here again soon. Everything was clean. Unique place with everything you need to enjoy your stay.

The Innsbrook Oasis by Innsbrook Vacations!
We had a wonderful time enjoying innsbrook! The home was spacious and had tons of outdoor room. We did have some ants visit the kitchen, but as soon as we told the owners they brought over some ant spray. Will definitely stay here again!

The Treetop Escape by Innsbrook Vacations!
Over exceeded expectations

Katy Haus: Hot tub, Wineries, Fenced yard, Dog-fri
The place was comfortable, clean and we loved the location! High recommend!

Spacious & Centrally Located Apt (Sleeps 8)
Joe’s place is more spacious than it looks in the photos. It is tucked in on a quiet street just minutes from downtown. Joe was super responsive with messages and answered my call upon check-in right away. The apartment had a variety of sleeping arrangements, perfect for my family. We really appreciated the board games and cable tv! :)

River View Cottage
What a Great getaway cabin. Perfect private spot with an amazing view to go with it. I would highly recommend this place to anyone!

Bank Haus - USA Today Travel - Hot Tub, Fenced Yar
Really enjoyed our stay at the Bank Haus; Nat & Tyann were extremely responsive and helpful, and the operational parts of our visit were entirely trouble-free. The pizza place next door, Philly’s, was a pleasant surprise, and the nearby distillery in New Haven (Pinckney Bend) was a great time. We don’t often revisit the same Airbnb destination, but I might make an exception here! Thanks again, Nat & Tyann!

Featured on USA Today - Hot tub, Fenced Yard
We had a great weekend here. The space was clean, comfortable, and beautifully put together. It was also dog friendly, which made things so much easier for us. The hosts were kind, responsive, and shared great suggestions that helped us make the most of our time in the area. We were especially touched by the welcome gift of local wine and coffee. Overall, a lovely stay and we'd absolutely come back.
Family- and pet-friendly home rentals

Luxury 2BD/2BH in Historic CWE/1E M
My friend and I showed up to the AirBnB an hour after a Tornado hit, so very bad timing, but Hui Mei did everything you could ask of from a host. Obviously she had no control over what happened, but she made sure we were taken care of and made last minute changes to accommodate us, make sure we were safe, and that we had power when many people did not. Could not recommend her more. And the place was also great, no complaints at all.

Zoo Bungalow - Across the street from the STL Zoo
We loved staying here. Being a short walk to the zoo was fun for the kiddos. Lauren's place is very kid friendly and she was very responsive and helpful. We will definitely stay again.

Historic Benton Park Completely Redone Apartment
Second time staying here. Clean, great location near a park, and great pet policy!

*Historical* Aletha-Marie Krog Guest House
This place belongs in a magazine. Adorable and clean home in the heart of Washington. Super cute and all rooms are big and beds are comfy! Decor is lovely and it has the old charm. We enjoyed the snacks provided by owners and the local recommendations. Would absolutely recommend and stay here again.

Trendy + Spacious Shaw Duplex
Loved the place, the house had a lot of neat decor and space.

Leamington Lounge
Adrian’s place is lovely! Awesome hospitality and a quiet St. Louis neighborhood close to wonderful restaurants and cool things to do. We are local, but stayed here due to some damage to our home and absolutely loved the place! Highly recommend this place for a great St. Louis visit!

Great Deal in Botanical Garden Area
The unit was charming and clean. Chris had games available to play for down time. The home is near a ton of restaurants and not far from any attractions you may want to visit. It's a great place to relax and unwind in a quiet, cute neighborhood on the edge of the botanical gardens.

Westerfield Log Cottage
This was a beautiful and peaceful cabin surrounded by farm land. The flower gardens were a nice added touch to the property. We had a great time.
Family-friendly home rentals with a pool

Heaven's Gate
Thank you Kim for making sure everything went well. The surrounding countryside is absolutely beautiful. Thank you for sharing your beautiful home!

Private indoor pool & sauna
We came for a graduation for our daughter. She and her husband and four kids stayed with us. Deborah went above and beyond to make us feel welcome! There were graduation decorations and even bubbles for the kids to help Mom celebrate! She left little surprises all over the house for our grandkids and they were so entertained by such a well stocked home! The pool was way nicer than expected and we had so much fun in it!! You can tell Deborah takes pride in this home and in providing a memorable experience! This was actually a last minute booking because our original place was canceled and I feel it was meant to be. This was a better weekend because of where we stayed!

Clark Brick House w/ Pool | Historic St. Charles
The house was amazing and clean. The pool area was peaceful after a long day of work. It was conveniently located to where we were working and were able to walk back and forth. The host was responsive to any questions and requests. I would definitely stay here again. Thank you!

4BR/2BA Mod Home w/ Private Heated In-Ground Pool
Deborah went above and beyond such an awesome place! The kids also had so much fun! We loved the pool area when it was not raining! Definitely would come back here!
Quick stats about holiday rentals that are family-friendly in Chesterfield
Total rentals
20 properties
Total number of reviews
240 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Destinations to explore
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- Busch Stadium
- Six Flags St. Louis
- Saint Louis Zoo
- Central West End
- Enterprise Center
- Gateway Arch National Park
- Missouri Botanical Garden
- City Museum
- St. Louis Aquarium at Union Station
- Cuivre River State Park
- Pere Marquette State Park
- Meramec State Park
- The Winery at Aerie's Resort
- Saint Louis Science Center
- Castlewood State Park
- Cathedral Basilica of Saint Louis
- Missouri History Museum
- Grafton Winery the Vineyards
- St. Louis Country Club
- Norwood Hills Country Club
- Hidden Valley Ski Resort
- Adventure Valley Zipline Tours and Paintball Park
- Boone Valley Golf Club
- Raging Rivers WaterPark