Orlando couples looking for trendy and affordable Labor Day getaways are in luck! Six Florida locales recently made the list of “Top Trending & Most Affordable Labor Day Getaways.” This ranking was conducted by HomeToGo, a vacation rental marketplace.
Trendy Labor Day Getaways Drivable from Orlando
A federal holiday in the U.S., Labor Day is observed on the first Monday of September (i.e., 9/1/25), honoring the labor movement and the contributions of workers. Many employers grant staff the day off with pay. To maximize the upcoming three-day holiday weekend, check out these trendy couples getaways that you can drive to from Orlando.
The trendiest Labor Day getaways in Florida:
St. Augustine Beach (#8)
HomeToGo reports a +316% year-over-year search increase for St. Augustine Beach, landing this destination in the Top 10 at #8. And I think I know why!
St. Augustine is among the most romantic towns in the country; thus, Orlando Date Night Guide has a whole section dedicated to it!. The “Ancient City” even ranked third on “140 Most Romantic Small Towns in America,” a list by New York Travel Guides. St. Augustine boasts charming pastimes, scrumptious restaurants and breathtaking scenery, including St. Augustine Beach.
Situated on Anastasia Island, St. Augustine Beach is accessible just over the Lion’s Bridge, off the Historic Downtown District of St. Augustine. Once you’ve crossed over this short bridge—atop of the Matanzas River—it feels like you’ve entered a completely different town. Gone is the Spanish architecture, iconic landmarks and bustling streets… swapped out for quiet beachy vibes.
St. Augustine Beach is about an hour and forty minutes northeast of Orlando. Click over to our post, “Three Perfect Days in St. Augustine Beach.” Yup, that’s exactly what you need for this Labor Day getaway!
Indian Shores (#13)
The entire Tampa Bay region is epic for date nights and couples getaways. In case you haven’t heard, Tampa Bay Date Night Guide is our sister site. Indian Shores is boasting a +271% year-over-year search trend increase. Indian Shores is a great couples’ getaway for Labor Day weekend because it blends the charm of a quiet Gulf Coast town with plenty of ways to reconnect before summer ends.
Indian Shores sits between the busier hubs of Clearwater Beach and St. Pete Beach, so couples get soft white sand and warm Gulf waters without bigger crowds. It’s perfect for long hand-in-hand walks, shell collecting or watching a fiery sunset over the water.
Plus, the area has plenty of beachfront condos, boutique hotels and vacation rentals where couples can enjoy a private balcony, morning coffee with ocean breezes and evening wine to the sound of waves. And from intimate beachfront restaurants to casual tiki bars, Indian Shores has great options for foodie couples, like my hubs and me, who love to share fresh-caught seafood while soaking in the view.
For active couples, Labor Day weekend is a great time to rent kayaks, paddleboards or jet skis. The calm Gulf waters are beginner-friendly, and there’s also the Intracoastal Waterway for exploring mangroves and spotting dolphins.
Fort Myers Beach (#14)
Mostly recovered from the hurricane-caused devastation, Fort Myers Beach is seeing a +268% year-over-year search trend increase. Things aren't completely back to normal per se, but couples can absolutely enjoy a perfect mix of coastal beauty, romantic activities and laid-back charm in Fort Myers Beach this Labor Day weekend.
With summer crowds thinning just slightly before peak season returns, Orlando couples can wander along the white sands of Fort Myers Beach, take sunset cruises on the Caloosahatchee River or rent kayaks to explore Lovers Key State Park’s secluded waterways and wildlife.
The area’s vibrant downtown offers open-air dining at waterfront restaurants, live music venues and cute boutiques, while nearby Sanibel and Captiva islands provide quiet escapes for shelling, biking and beachfront picnics.
Mexico Beach (#18)
Inching into the Top 20, Mexico Beach ranks #18 for the trendiest Labor Day getaways. I’m not gonna lie… I was surprised to see this lesser-known Florida locale pop up on the list with a +228% year-over-year search trend increase.
Mexico Beach is nestled along the Panhandle’s coastline, about 30 minutes south of Panama City. This small-town gem can lead to big-time core memories if you envision uncrowded sugar-white beaches and crystal-clear Gulf waters. Couples can rent bikes to explore the streets, browse local art galleries, or book a boat tour for dolphin spotting and island hopping.
Nearby restaurants serve up Gulf-to-table fare in cozy, waterfront settings, while vacation rentals and boutique inns provide intimate accommodations with balconies overlooking the water. Over Labor Day weekend, the warm weather and gentle breezes make for ideal beach lounging, paddleboarding or simply unplugging together in an unexpected spot.
Affordable Labor Day Getaways Drivable from Orlando
Tarpon Springs (#1)
Holy Mackerel—or should we say holy tarpon—because Tarpon Springs ranks #1 for the most affordable Labor Day getaways. According to this report, $170.20 is the median nightly price.
Labor Day weekend doesn’t afford enough time to travel aboard to Greece. But Tarpon Springs is an affordable alternative. Located just north of Clearwater, this dreamy destination captures the spirit of Mykonos with its rich Greek heritage, but without the international airfare.
Click over to our blog, “Tampa Bay’s Hidden Gem: Exploring Tarpon Springs” to start planning your itinerary.
Cedar Key (#6)
FYI, Cedar Key is a fav of our editor, Dani. And with a $207 median nightly price, you'll probably want to check it out for yourself. All you need to know is housed on our website, thanks to Dani's expertise, including Cedar Key restaurants, hotels and beaches.
Go… Getaway for Labor Day
A HomeToGo spokesperson told Orlando Date Night Guide that overall searches for vacation rental stays during the holiday Labor Day weekend are up by +26% in comparison to last year. Sixty-three percent of U.S. vacationers are planning domestic trips; are you and your love? Well, go ahead… getaway to Florida’s top trending and affordable Labor Day getaways.
