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Top Florida Staycation Ideas Within a Few Hours of Sarasota County
By Tracy  Jones, Local Venice Real Estate Expert
Living in Sarasota County means we’re blessed with not only a beautiful home base, but also countless dreamy destinations just a short drive (or boat ride!) away. Whether you’re in need of rest, reconnection, or a little indulgence, these staycation spots offer something special without the stress of airports or big travel plans.
Here are my top Florida staycation ideas—all within a few hours of home:
🏝️ 1. Cabbage Key – An Old Florida Treasure (About 2 hours + boat ride)
This off-the-grid gem feels like stepping back in time. Accessible only by boat (or seaplane), Cabbage Key is famous for its “dollar bill walls” at the island inn and the juicy burgers that inspired Jimmy Buffett’s Cheeseburger in Paradise. Stay in one of the waterfront cabins and enjoy sunrise coffee with dolphins swimming by.
Pro Tip: Bring your camera—sunsets here are unforgettable. It’s perfect for a quiet writer’s retreat, a romantic weekend, or simply unplugging from it all.
🌊 2. Fort Myers Beach – Fun, Sun, and a New Beginning (1.5 hours south)
Fort Myers Beach is rebuilding beautifully, and now is a great time to visit and support the area’s resurgence. Enjoy soft, wide beaches, live music, and waterfront bars along Estero Boulevard. It’s still got that laid-back beach town energy, but with new life being breathed into every corner.
Stay Tip: Choose a beachfront inn or vacation rental near Times Square for walkability and fun.
🏖️ 3. Sunseeker Resort, Port Charlotte – Poolside Paradise (Under 1 hour south)
Want to feel like you’re on a luxury Caribbean getaway without leaving Southwest Florida? Sunseeker Resort in Port Charlotte is a game changer. Their massive pool and private cabanas, full-service spa, and elevated food court(featuring everything from sushi to upscale Italian) make it the perfect overnight escape—or even a daycation.
Why I Love It: It’s ideal for couples, best friends, or even a solo stay to recharge. Book a cabana, sip a cocktail, and watch the sun melt into Charlotte Harbor.
🌴 4. Captiva & Sanibel Islands (1.5–2 hours south)
These sister islands offer a serene escape filled with shell-covered beaches, winding bike paths, and boutique accommodations. Captiva is more secluded and romantic, while Sanibel is perfect for nature lovers and families alike.
Don’t Miss: The Shell Museum and a kayak tour through Tarpon Bay’s mangroves.
🏝️ 5. Anna Maria Island (Under 1 hour north)
This is my go-to for an easy, breezy beach day or overnight. Think colorful cottages, mom-and-pop ice cream shops, and toes-in-the-sand restaurants. It’s charming, authentic, and still delightfully under the radar.
Insider Tip: Rent bikes to explore Pine Avenue and the City Pier for a full-day adventure.
🎨 6. St. Petersburg Arts & Culture Weekend (1 hour north)
Explore museums, murals, indie coffee shops, and rooftop bars—all along a walkable waterfront. A perfect destination if you’re craving inspiration, conversation, or a weekend full of creativity.
Stay Tip: Book The Don CeSar for a luxurious beach-meets-culture experience.
🌲 7. Myakka River State Park Cabins or Glamping (30–45 minutes east)
Get back to nature with a stay in a rustic cabin or a luxury tent. You’ll find hiking trails, airboat rides, and wildlife sightings galore. It’s a peaceful contrast to our beachy lifestyle—and a great reminder of Florida’s wild side.
🛶 8. Crystal River & Weeki Wachee Springs (2.5 hours north)
Swim with manatees, paddle spring-fed rivers, and take in the kitschy charm of live mermaids. Crystal River and Weeki Wachee offer both quirky fun and natural beauty.
Tip: Great for families or adventurous day-trippers.
💆‍♀️ 9. Lakewood Ranch Spa Staycation (30 minutes north)
Not in the mood to travel far? Book a room at the Carlisle Inn and enjoy a day of pampering at one of the area’s wellness spas. Top it off with a lakeside dinner at Waterside Place.
🌟 Final Thoughts
Living on the Gulf Coast isn’t just a lifestyle—it’s a launchpad to explore the very best of Florida. From barefoot beach getaways to boutique resort experiences, there’s something within reach for every kind of traveler. These nearby gems are the reason so many people dream of living here… and why I’m proud to help them make it a reality.
Thinking of making one of these places your second home—or just want to invest where others vacation? Let’s talk strategy. I’m here to help you live the Florida life you’ve imagined. 🌴
– Tracy Jones, Realtor® | Sarasota County Real Estate Expert
“Where you stay says a lot about how you live. Let’s make your next chapter extraordinary.”
