How is drainage managed for the planter? Florida is mostly dry during winter and spring with the rainy season beginning in summer. Of course, hurricanes mean extreme rain. Your planter needs excellent drainage to keep it from becoming bog-like during such rains. Use a hammer-drill to put drain holes along the bottom of the planter. Then fill the planter to the top with a good quality garden soil.

Here are some vines for the fence. Bambino Bougainvillea stays small and can even be grown as a shrub. Bougainvillea prefers a cramped root system as long as soil is free-draining, and it doesn't mind heat. Scarlet Honeysuckle (Lonicera sempervirens) is native to the U.S. And blooms through summer. Mexican Flame Vine (Pseudogynoxys chenopodioides) grows 8-10' tall with yellow to orange daisy blooms. Black-eye Susan Vine or Clock Vine (Thunbergia alata) is an annual that likes heat. Coral Vine or Queen's Wreath (Antigonum leptopus) grows 10-12' in my yard with pink flowers late summer until frost. The information in the links suggest these vines grow quite tall, but keeping their roots constrained as well as pruning when needed will keep them smaller.

As for your previously grassy areas, try some full sun ground covers or other perennials that will take heat and dryer soil. Shore Juniper (J. conferta) and Creeping Juniper (J. horizontalis) grow from 6" to 18" tall depending on cultivar, but can cover up to 10' wide at maturity. Perennial Peanut (Arachis glabrata) used to be only for pasture forage, but is becoming a drought-tolerant ground cover that needs no fertilizer. This LINK has a list of ground covers for Florida. Choose from those that grow in full sun, but you should also look them up to see if they are drought tolerant as well. Remember that anything you plant will need to be watered the first year. Once plants are established they should only need supplemental watering during extended dry periods.

@mindshift Thank you so much for all this info. I noticed that one out of four planters has a drain hole. I'll do some research on the plants that you mentioned and get back to you with any questions.

You can't have vines growing all over gates that need to slide open and close or big bushes that get too wide. You need tall and skinny. Plant Ti Leaf or Dracaena in the planter boxes.