Why a Weekend Getaway in Florida Is All You Need
Need a reset but don’t have a full week to spare? Florida weekend trips are the answer.
With sun-soaked beaches, spring-fed swimming holes, and charming towns just a short drive away, weekend getaways in Florida feel like mini-vacations with major rewards. Whether you’re planning a romantic escape, a family adventure, or a spontaneous solo trip, Florida’s got a spot with your name on it.
No passport, no long flights, just pack a bag and go.
Over 130 million visitors explore Florida yearly, plenty of them just for the weekend.
Florida Weekend Trip Planner: What to Know First
Planning a weekend getaway in Florida? Here’s the inside scoop before you book.
First things first, when to go. If you want warm sunshine without the theme park lines or beach crowds, aim for late spring or early fall.
You’ll still get amazing weather, but skip peak season’s chaos (and inflated prices). Winter weekends can be dreamy, especially in South Florida, where “cold” means 70° and sunny.
Getting around? Florida’s road trip game is strong. Most major destinations like Orlando, Miami, and Clearwater are just 2–4 hours apart by car. But if you’re flying in, snag early morning or late-night flights for cheaper fares and lighter traffic.
Now, let’s talk about where to stay. Hotels are fine, but if you’re traveling with family or friends, vacation homes give you way more space, privacy, and freedom.
Want your own kitchen? A private pool? A quiet lanai for sunset drinks? That’s why short Florida vacations feel longer (and better) in a rental.
Top Weekend Getaway Destinations in Florida
1. St. Augustine – History, Charm, and Walkable Streets
Step back in time in America’s oldest city, where cobblestone streets, Spanish forts, and haunted pubs make every corner an adventure. Explore the Castillo de San Marcos, take a walking ghost tour, or just sip wine under the oak trees. It’s the kind of romantic weekend getaway that feels like Europe without the passport. Great for couples, history lovers, and travelers who love to explore on foot.
2. Clearwater Beach – Sugar Sand, Sunsets, Dolphin Spotting
Looking for a postcard-perfect beach? Clearwater Beach is all about soft white sand, crystal waters, and those golden Gulf Coast sunsets. Watch street performers at Pier 60, hop on a dolphin cruise, or simply float the day away. It’s one of the best Florida weekend trips for families and beach lovers, and a great spot for renting a Florida vacation home near the water.
3. Miami – Art, Nightlife, and World-Class Dining
Miami is calling if your ideal weekend includes rooftop cocktails, colorful murals, and late-night bites. Explore the Wynwood Walls, wander through Little Havana, and make time for a beach sunrise. Whether you’re traveling with friends or someone special, this short Florida vacation blends tropical energy with big-city flair. Pro tip: Stay in a rental near the action so you can live like a local for the weekend.
4. Everglades National Park – Nature Lovers + Eco-Tours
Craving something off the beaten path? Trade flip-flops for hiking boots in the Everglades, where you can paddle through mangroves, spot gators on an airboat, and unplug for a while. This is one of the best hidden Florida spots for weekend warriors, solo travelers, and eco-minded explorers. Don’t forget your bug spray and your camera.
5. Anna Maria Island – Quiet Beach Vibes for Couples/Families
Tucked away on Florida’s Gulf Coast, Anna Maria Island is all about slow mornings, bike rides, and seafood by the pier. This is one of those relaxing Florida destinations where time seems to pause. Great for family weekend getaways or couples who want soft waves and no stress. Rentals here feel more like home, especially if you score one with a pool or porch swing.
6. Orlando (Beyond Theme Parks) – Local Eats, Lakes, and Hidden Gems
Orlando isn’t just theme parks, though Disney’s always a good time. For a refreshing twist, check out Lake Eola Park, the Ivanhoe Arts District, or grab tacos in Mills 50. Paddle a swan boat, visit local museums, or explore nearby springs for a fun and affordable Florida weekend trip. Great for families, groups, and anyone who wants more than roller coasters.
7. Crystal River – Manatees and Spring-Fed Swimming
For a truly unique Florida weekend, head to Crystal River, where you can kayak through freshwater springs and even swim with manatees. This quiet town offers a peaceful, nature-filled getaway perfect for couples, families, or travelers seeking something different. It’s one of the few places in the world where you can legally snorkel with these gentle giants. Pack a GoPro!
8. Key Largo – Snorkeling and Laid-Back Island Escape
Key Largo kicks off the Florida Keys with calm waters, coral reefs, and some of the best snorkeling in the state. Spend your weekend diving, paddleboarding, or sipping drinks on a dock while the sun sets. Ideal for couples, scuba enthusiasts, or anyone chasing that island vibe without heading too far south. Don’t miss John Pennekamp Coral Reef State Park, it’s a must.
Quick Packing Tips for a 2–3 Day Florida Trip
Packing for a Florida weekend getaway? You won’t need a full suitcase, but a few smart choices can make or break your trip. Whether you’re beach-bound, theme-park hopping, or exploring hidden Florida spots, here’s what to bring so you’re prepped, not stressed.
Essentials You Shouldn’t Skip
Florida sun is no joke, even on overcast days. Make sure these items are at the top of your list:
- Sunscreen (reef-safe if you’re swimming)
- Bug spray (a must for springs, trails, and the Everglades)
- Water shoes (great for kayaking, springs, or rocky beaches)
- Sunglasses + hat for that full sun protection combo
- Refillable water bottle—hydration is key in the Florida heat
These basics work for almost any destination, from Crystal River’s spring-fed swimming to Clearwater Beach’s soft sands.
Small Tech = Big Convenience
Keep your weekend smooth and selfie-ready with:
- Portable charger (especially if you’re out all day at the parks or beach)
- Travel-size toiletries (Florida humidity isn’t kind to bulky bags)
- Waterproof phone pouch for paddleboarding or sudden rainstorms
- Zip-up daypack or tote for day trips and beach runs
Whether you’re enjoying Florida weekend trips in St. Augustine or a quick eco-tour through the Everglades, you’ll want easy, grab-and-go gear.
Kid-Friendly Must-Haves (If You’re Traveling with Little Ones)
For those planning family weekend getaways in Florida, keep kids happy and meltdown-free with:
- Snacks and refillable sippy cups
- Small toys, books, or travel games
- Swim vests or puddle jumpers (especially for pool homes or beaches)
- Wet wipes, extra clothes, and sun hats
Bonus tip from the moms: Pack a mesh laundry bag; it’ll help you keep track of sandy swimsuits and beach towels.
Plan Like a Local: Florida Weekend Travel Tips
Want your weekend to feel less like a tourist scramble and more like a breezy local escape? Here are some smart Florida travel tips that seasoned weekenders swear by.
Skip the Friday Traffic Jam
If you’re driving or checking in on a Friday, aim for midday arrival. Major highways like I-4 (Orlando) and I-95 (South Florida) can get jammed between 4–7 PM. The earlier you arrive, the sooner you can kick off your getaway. No one wants to start their trip in bumper-to-bumper traffic.
Book Tours Early—They Fill Fast
From dolphin cruises in Clearwater to airboat rides in the Everglades, weekend tours tend to book out quickly, especially in peak season. Lock in your spot early, even before you pack. This is especially true for family-friendly activities and sunset excursions.
Eat Like a Local
Forget the chain restaurants. Look for fresh seafood markets, family-run Cuban cafés, or beachside taco shacks. Spots like Pine Avenue on Anna Maria Island or Little Havana in Miami offer flavors you won’t find on a tourist strip. If it looks low-key but smells amazing? That’s the one.
Use Smart Filters When Booking
When searching for Florida vacation homes for rent on Airbnb or VRBO, use filters like “entire place,” “family-friendly,” and “self-check-in” to find stays that feel easy, safe, and private. Look for homes with full kitchens, washer/dryers, and high guest ratings—they’ll make your weekend smoother from the jump.
Where to Stay: Vacation Homes vs. Hotels
Let’s be honest, weekends fly by, so where you stay matters a lot.
While hotels may check the basic boxes, vacation rentals offer something more personal, flexible, and spacious.
Think about it: Would you rather stay somewhere that limits you to no kitchen to cook in, no backyard for a BBQ, and extra rooms costing a fortune, or stretch out in a private vacation home where your family can truly enjoy the weekend together, without the compromises?
Why Vacation Rentals Win the Weekend
- More room to breathe – Separate bedrooms, roomy living areas, and no noisy neighbors through the wall
- Kitchen = money saved + midnight snacks – Whether you’re cooking up fresh seafood or heating leftovers from a local Cuban spot
- Privacy – No crowded lobbies or surprise housekeeping knocks
- Perfect for families or groups – Everyone gets their space, but you’re still together under one roof
Rentals That Feel Like a Getaway
At FunStay, our homes are curated for the way real travelers vacation. That means kid-friendly features (like cribs, bunk rooms, and splash pools), fully stocked kitchens, and locations close to Florida’s top weekend spots, whether you’re planning a family trip to Orlando or a quiet escape to Anna Maria Island.
We’re picky about what we offer, so you don’t have to be.
Make Your Florida Weekend Count
Sometimes, two or three days is all it takes to reset your soul. Whether you’re chasing sunsets or just quiet mornings, make it memorable.
Explore our vacation homes, family-ready, couple-approved, and perfectly placed for your next Florida weekend.
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