Born and raised in Florida this list in comprised of all my favorite cheap places to go and cheap things to do with my family.
Some places and ideas listed are just one or two hours of fun and some are all day fun!
(All prices,dates and times should be verified before visiting. Please verify with venue websites where applicable)

Castle Park Playground
255 S. Denning Drive Winter Park, FL 32789

cityofwinterpark.org/departments/parks-recreation/playgrounds/community-playground

Often referred to as the “castle park,” the Winter Park Community Playground is a very large wooden structure that allows imaginative play activities. I played there as a kid so it's a nostalgic place for me. Designed by nationally known playground designer Robert Leathers, this playground is quite unique and has climbing features as well as swings and a slide. There are public restrooms and a neat exercise trail as well. Bring a picnic lunch and a couple sports balls to throw on the lawn.

Hours of Operation:
8:00 AM to Dusk

Cost:
FREE!! 

Monkey Joes

Winter Park
5471 Lake Howell Road Winter Park, FL 32792

www.monkeyjoes.com

FUN FUN FUN! Tons of different inflatables to jump, slide and play on. The soothing sounds of the inflatables' fans always keeps my calm while the kids run like well, monkeys from one place to the other climbing and sliding every which way. I have to admit, I have had fun racing down a few slides to try to beat my little ones to the bottom. There is a toddler jumping area and a parent area with wifi and a TV.

Hours of Operation:
Mon-Thr 10:30-8
Fri 10:30-10
Sat 10-10
Sun 11-8

Cost:
$10.99 per Child
Adults are FREE!
$6.99 Children 2 and under if playing
Wednesdays are BOGO in the summer. Call ahead to double check first.

Park Avenue in Winter Park

Koi ponds on Park Avenue Winter Park

experienceparkavenue.com

There is so much to see and do on Park Avenue in Winter Park, FL. Window Shop, picnic in Central Park park, people watch and more! On Saturdays there is a Farmers Market. Be sure to check out the rose garden by the Sunrail and the huge koi fish in their ponds inside the store halls.

Cost:
Free unless you buy something.

Popcorn Flicks in the Park
251 S. Park Avenue Winter Park Fl.

www.enzian.org/film/popcorn_flicks

Popcorn Flicks features classic films for the whole family. Popcorn Flicks are usually held on the second Thursday of each month. The films are FREE and open to the public. You are encouraged to bring a blanket, a picnic or snacks.

Hours of Operation:
Please visit the website for actual dates and times.
Usually held on the 2nd Thursday of Each Month.
Movies are schedules to start at 8:00 PM but may not start until sunset to provide an optimal viewing experience.
Movies can get rained out

Cost:
FREE

Regal Summer Movie Express
Winter Park Village Stadium: 510 N. Orlando Ave., Winter Park FL 32789

www.regmovies.com/Movies/Summer-Movie-Express

Dollar movies all summer long! 9 weeks of popular recently released movie titles rated G or PG. There are 2 titles to choose from each week.

Personal Recommendations:
Arrive early. There are lots of Preschool and Summer Camp groups that take advantage of this great deal too! 
Get a Regal Crown Club Card it's free! Earn credits for buying tickets and concession items and get rewards like free popcorn, drinks and movie tickets!
See a long line?! No worries, Regal is prepared to open a second theater if needed to accommodate everyone.

Hours of Operation:
Tuesday and Wednesday 10 AM

Cost:
$1.00 per person

Shady Park Splash Fountain and Community Pool
721 W. New England Ave. Winter Park, FL

cityofwinterpark.org/departments/parks-recreation/recreation-sports/community-center

Shady Park is home to a few fun things to do! There is a Splash Fountain. There is also a Neos Wall Electronic Play System that has 9 different games. Most importantly the zero entry pool with splash features where you can cool off on a hot Florida Day. Ther pool reaches a maximum depth of just under 5 feet. Check the website for Monthly Dive-In Movie dates and times as well!

Hours:
 The pool is a seasonal amenity that opens in May 3 and closes the last weekend in September. 

May 3-June 6
Monday-Friday Closed
Saturday 12pm-6pm
Sunday 12pm-6pm

June 7-August 15
Monday-Friday 12pm-5pm
Saturday 12pm-6pm
Sunday 12pm-6pm

August 16-September 27
Monday-Friday Closed
Saturday 12pm-6pm
Sunday 12pm-6pm

Cost:
Splash Fountain and Park Area are FREE
Community Pool: 
$2.00 per resident
$4.00 per non-resident.
10 visit Passes and Family Season Passes are available as well.