When it comes to family vacations, few things rival the magic of a Florida road trip. From pirate legends and rocket launches to manatee sightings and pastel beach towns, the Sunshine State is a living postcard packed with family-friendly moments. But this isn’t just any road trip—it’s STR-style. That means no cookie-cutter hotel rooms or parking lot views. We’re mapping out a route that pairs engaging family destinations with vacation rentals that offer room to breathe, kitchens to cook in, and living spaces made for memory-making. Ready to load up the car? Let’s hit the road.
Stop 1: St. Augustine – Where History Feels Like Adventure
📍 Start here if you’re coming from the north (Jacksonville Airport is 1 hr away)
As the oldest city in the U.S., St. Augustine is bursting with interactive, kid-friendly history—minus the museum fatigue.
Family Favorites:
🏰 Castillo de San Marcos: Watch cannon firings and explore old stone corridors.
🗺️ Pirate & Treasure Museum: Hands-on exhibits and real artifacts from the golden age of piracy.
🍦 Avilés Street & Ice Cream Crawl: Colonial charm meets sweet treats on the oldest street in America.
STR Tip:
Book a colonial-style rental in the historic district—think exposed beams, shady courtyards, and walkable charm.
Stop 2: Orlando – Theme Park Capital Meets STR Comfort
📍 2.5 hrs from St. Augustine
There’s no skipping Orlando—it’s the nucleus of family fun. But staying in a short-term rental instead of a resort makes the experience less chaotic and more connected.
Must-Do’s:
🎢 Universal’s Islands of Adventure: Thrill rides + Harry Potter + splash zones.
🐊 Gatorland: Florida’s original attraction, with zip lines over gator ponds.
🚀 Kennedy Space Center (1 hr east): Epic day trip for future astronauts.
STR Tip:
Stay in Kissimmee or Reunion for rentals with private pools, game rooms, and enough bedrooms for the whole crew. Bonus if you find one with bunk beds!
Stop 3: Sarasota – Beach Days & Natural Playgrounds
📍 2 hrs 15 min from Orlando
Sarasota is a quiet treasure for families—fewer crowds than Clearwater, better beaches than most, and a cultural scene that doesn’t skimp on fun.
Family Highlights:
🦋 The Ringling Museum & Circus Collection: Interactive galleries + gardens to roam.
🏖️ Siesta Key Beach: Powder-soft sand, calm surf, and epic sunsets.
🐊 Myakka River State Park: Airboat rides, canopy walkways, and gator spotting.
STR Tip:
Book a colorful coastal cottage on Siesta Key or a downtown loft near shops and cafes. Look for walkability and beach gear included.
Stop 4: Fort Myers & Sanibel – Shells, Trails & Island Time
📍 1 hr 30 min south of Sarasota
Still recovering from recent storms, Fort Myers and Sanibel are bouncing back with resilience—and their nature-forward family appeal is stronger than ever.
Best Bets:
🐚 Sanibel Lighthouse Beach Park: Shell collecting + calm wading waters.
🐬 Tarpon Bay Explorers: Kayak eco-tours with dolphin and manatee sightings.
🚲 J.N. “Ding” Darling Wildlife Refuge: Biking through mangrove forests and bird habitats.
STR Tip:
Choose a canal-side STR in Cape Coral or a Sanibel bungalow with bikes and screened porches.
Stop 5: The Florida Keys – End in Island Paradise
📍 4–5 hrs from Fort Myers (with scenic bridges all the way)
Wind down the trip in the Florida Keys, where adventure and chill co-exist beautifully. This is where family moments stretch out over hammocks, kayaks, and sandy toes.
Don’t Miss:
🐠 John Pennekamp Coral Reef State Park (Key Largo): Snorkeling heaven for all ages.
🦎 The Turtle Hospital (Marathon): Hands-on conservation and turtle rehab tours.
🏝️ Key West Butterfly & Nature Conservatory: A peaceful wrap-up with tropical beauty.
STR Tip:
Split your stay: one night in Islamorada for luxury and water access, and another in a classic Key West conch house with a backyard oasis.
This isn’t just a road trip—it’s a front-row seat to Florida’s most magical family experiences. And by choosing STRs that offer space, personality, and kid-friendly perks, you’ll trade cramped hotel nights for movie nights, home-cooked dinners, and backyard swims. So pack the car, prep the playlist, and get ready to make Florida memories that last well beyond the final stop.
