Family-friendly vacation 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.

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Guest favorite

Apartment in St. Louis

4.94 out of 5 average rating, 587 reviews

Come stay in STL’s little Italy, ‘The Hill' NBHD

Renovated flat, In St Louis's 'The Hill' NBHD. This 1-bedroom, 2-bed apt. is centrally located near; Forest Park, BJC Hospitals, Universities, Downtown, & sporting venues. Walk to restaurants, or stay in and cook! Lovely private, bedroom w/ a queen bed. Great living room w/ cool exposed brick, & a comfy sofa & futon (converts to 2nd queen bed). Beautifully tiled walk-in shower & double sink vanity in the bathroom. In-unit washer/dryer. Private front porch. Chromecast on TV, wifi, & easy check-in

Jan 15 – 22

G$18,369 GYD per night

Guest favorite

Home in Saint Charles

4.98 out of 5 average rating, 494 reviews

301 Guesthouse SuperHost/Shop Discounts/Katy Trail

Our 301 Guest House is new and completely remodeled in 2018! It’s ideal for one or two people with beautiful furnishings, great queen bed, lots of amenities, full kitchen, with big back yard and patio to enjoy outdoors too! Cable and FAST WiFi! Enjoy light Breakfast! BEST location, Great events year round within walking distance, with being only about 2 blocks from S. Main St, where there are about 100 gift shops n restaurants! Katy Trail is so close, with Spring, Summer, Fall and Xmas events!

Oct 23 – 30

G$28,431 GYD per night

Guest favorite

Condo in University City

4.89 out of 5 average rating, 227 reviews

Modern Condo on Delmar Loop; Central to Everything

This absolutely stunning condo in the Delmar Loop are has everything you could need. Located only 100 feet from Delmar and a short walk to WashU Campus or Forest Park. Metro Link is only a 10 minute walk away. Perfect for visits to WashU for college visits and graduations! The Pageant and Delmar Hall making this the perfect condo to stay in to see your favorite band! One off-street parking spot in a gated parking lot. The entire condo community is gated & equipped with video surveillance.

Aug 24 – 31

G$24,690 GYD per night

Guest favorite

Loft in St. Louis

4.99 out of 5 average rating, 228 reviews

Renovated Loft Near Soulard and Downtown

Located in the Cherokee-Lemp Historic District, this newly renovated 1,200SF 2nd floor apartment provides everything needed for a comfortable stay away from home. Private access to open loft space, lots of natural light, modern kitchen, large living area, private bedroom and full bath. Walking distance to restaurants & bars, bakeries, antique & specialty shops, galleries & other venues. Close proximity to Downtown, Soulard, Forest Park, Museums, Universities & other points of local interest.

Jan 3 – 10

G$24,887 GYD per night

Guest favorite

Guest suite in Belleville

4.95 out of 5 average rating, 191 reviews

Aunt Vi's Apt by Belleville Historical Society

Studio apartment furnished in authentic mid century style. Licensed and inspected. 15 minutes from downtown St Louis with the Arch, Busch Stadium, home of the Cardinals, Cahokia Mounts historical site, 15 min. from historic downtown Belleville, world famous Art on the Square. Apartment minutes from locally owned shops, restaurants and brew pub. Appropriate for world travelers interested in architecture, tour the in progress MidCentury Architecture Museum right outside your turquoise door!

Oct 9 – 16

G$19,081 GYD per night

Guest favorite

Cabin in St Charles

4.98 out of 5 average rating, 294 reviews

Camp Mill Pond: Historic Cabin Near Main Street

*St. Louis Magazine A-List Winner!* ***PRESS: DESIGN STL, STL MAG, AND FOX2NEWS*** Camp Mill Pond is a throwback to the slow and easy rhythm of hot summer days. Full of campfire Wes Anderson inspiration, easy access to our historic area, including Main Street, Katy Trail for biking, Frenchtown, and all the joys of glamping. This 180-year-old historic cabin sits on a beautiful lot, shared with our 1865 three-story home and a two-story carriage house. Ask about renting bikes and a golf cart!

Oct 5 – 10

G$41,716 GYD per night

Guest favorite

Apartment in St. Louis

4.95 out of 5 average rating, 356 reviews

The Grove on Gibson 2

WONDERFUL 2bedroom/1 office 2nd Floor apartment! Keurig with coffee/cream/sugar provided (we may not have what you prefer so if there is something that you enjoy you will need to bring on your own). Kitchen tools to cook/bake or heat your next meal! Highspeed internet and TV with Amazon, Hulu, Netflixs, and local channels. Washer/dryer and ironing board in-house. Second floor unit and so we ask that consideration for 1st floor occupants is priority. NO PARTIES. No Cleaning Fee.

Oct 15 – 20

G$28,823 GYD per night

Guest favorite

Farm stay in Lake Saint Louis

4.92 out of 5 average rating, 194 reviews

Updated Farmhouse 2 bd 2 acres

Updated Farm House on 2 acres,3 beds, 1 bth, this house has 2 bedroom with 3 beds, a fully equipped kitchen, living room, a full bathroom,double sinks,and laundry facilities, this house is a duplex, with 2 separate units, the upstairs is for Airbnb guest, the lower unit has a tenant, each unit has its own space and entrance. 25 minutes from the St. Louis Airport, close to the Missouri Wineries, Bush wild life area, and only 10 minutes to the Katie Trail along the Missouri River.

Oct 1 – 8

G$25,669 GYD per night

Guest favorite

Home in Ballwin

4.94 out of 5 average rating, 136 reviews

Entire lower level of our home w/Paris Theme

Our home is located in a quiet West St. Louis County neighborhood. The lower/walkout of this place is your home away from home. It has a private entrance from a walk around sidewalk to the backyard. You will have the entire lower level of our home. We live in the upstairs or first floor of this home. Our place is best suited for one couple, solo adventurers, business travelers, and one family (with kids). This space has been recently remodeled with a French Parisian theme!

Sep 30 – Oct 7

G$21,044 GYD per night

Guest favorite

Home in St. Louis

4.93 out of 5 average rating, 496 reviews

Charming One bedroom house "On The Hill"

This one bedroom newly updated house is the perfect location for discovering all that "The Hill" has to offer. Within walking distance to some of the finest restaurants in all of STL. ( Zia's being our personal favorite) Enjoy a great meal and walk to one of the many well known bakeries, Italian markets, Shops, Coffee Bistro, Gelato and Bars. What more could you ask for? Only a short drive to downtown to see the City Museum or catch a Cardinals or Blues Game.

Jul 15 – 22

G$25,776 GYD per night

Guest favorite

Guesthouse in Marthasville

4.96 out of 5 average rating, 222 reviews

Hazel's House by the Katy Trail

In the heart of Missouri Wine Country. Within walking distance of the Katy Trail and Lake Creek Winery. Many wineries within a 25-30 minute drive. Enjoy a weekend getaway in a 2 bed 1 bath home. Hazel's House is clean, comfortable and private overnight accommodations. We are not a bed and breakfast, no food included, but there is coffee. Please make sure the location is suitable. We are located out in the country and the internet can be spotty.

Feb 26 – Mar 5

G$23,622 GYD per night

Guest favorite

Cottage in Maplewood

4.98 out of 5 average rating, 368 reviews

Weaver Guest House

This charming, light-filled cottage feels like its own private hideaway, yet it's close to everything St. Louis has to offer. Tucked between trees in a quiet Maplewood neighborhood, it's a 15-minute walk to the MetroLink and a 10-minute drive to Washington University, Webster University, Fontbonne University, Forest Park, and Clayton. Business travelers and families alike will appreciate the washer/dryer, fast WIFI and cable TV.

Jul 31 – Aug 7

G$23,252 GYD per night