The warmth and sun of Florida are a major attraction any time of year. Anticipate the cooling weather and return of fall and spend a little extra time in the sun and warmth with a trip to the Sunshine State’s fun and sun you won’t soon forget by heading to Siesta Key. Pack your bags and prepare for fun in the sun, water, and even on land as you check out many of the exciting activities there are to do and see while you cherish the last days of summer on your Siesta Key Labor Day weekend.

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Beach Time

An island vacation, no matter what time of year you’re here, without a visit to its beaches is virtually unheard of. You and your loved ones are only moments away from the luscious sand and vibrant waters of the Gulf of Mexico no matter where you are on the island. Fill the cooler, pack the beach gear, and stake your territory with blankets and umbrellas as you prepare for a day of lounging on the shore, or a dip in the Gulf.


Snorkeling is a great way to get in the water and explore the area, especially on the islands. Whether you rent gear from a local shop and explore on your own or book a charter tour, it’s a magical way to see the underwater world that surrounds Siesta Key this Labor Day. Adventurers looking to make their own fun should try Point of Rocks, a spot known for tide pools, moss-covered rocks, and sea life in an easily navigable and somewhat shallow area. If you’re looking for a group vibe, charter a boat with Key Life Charters where you can bring your own snacks, including adult beverages. Expand your snorkeling adventure by adding experiences like sightseeing, dolphin and wildlife spotting, and more for your unique and perfect trip.


Sail high over the water and gain a whole new perspective on where you’ve chosen to spend your Labor Day getaway with Parasail Siesta. You’ll take off from the deck of their specially designed and USCG-approved parasailing boat to fly high above the waters of the Gulf – up to 500 feet in the air! Keep watch on the water from your bird’s eye view for dolphins, turtles, manatees, stingrays, and other sea life. Stay dry throughout the flight or wear your bathing suit for a refreshing dip in the water before flying up again and coming down safely on the deck. Bring your waterproof or disposable camera to capture the memories from your perspective in the harness. Parasail Siesta takes several professional digital camera pictures of your flight and will provide you with a memory card at the end of the trip so you can develop your pictures whenever you like. Rides are approximately 15 minutes of airtime, but the whole excursion duration depends on the number of fliers.

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Private Cruise

There are plenty of boat charter companies that offer cruises. Stay out of the cooling waters of the Gulf while still enjoying marine activity. Watch the sunset, search for dolphins and other marine life like manatees and aquatic birds, or just sit back and relax as the captain steers through the sea. Sip on an adult or other beverage as you take in the beautiful Florida coast and Gulf waters with your loved ones for a great way to end any day of your stay. Daytime and sunset cruises are available.

Bicycle Rentals

Siesta Key has a land area of just 2.4 miles, so there are bound to be places to explore where your rental car just can’t reach. Instead of trying to see everything by car, get some exercise by exploring the many walking and biking trails that bring you closer to the sights inaccessible by car. Choose from single-seat bikes without gears (a.k.a. cruisers), tricycles for extra balance and basket space, children’s bikes, adult bikes with baby seats, or choose to take a romantic ride on a bicycle-built-for-two – there’s a bike to fit the needs of everyone in your group! Ask about locks and extra baskets as well as safety gear like lights and helmets, and even perks like delivery to your accommodations.

Labor Day Fun on Siesta Key

When you book your fun-filled getaway to Siesta Key, you won’t be hard-pressed to find activities to fill every minute of every day you’re here. Rent Siesta Key has a rental to fit your needs, from one-bedroom units all the way up to six bedrooms for a Labor Day reunion with friends or family. Fuel up for the day or bring the group together with a delicious home-cooked meal prepared in your unit’s fully equipped kitchen. When the day is done, relax in a private bedroom, or spread out in the open living area for a game, movie, or TV show together. When you’re not at the beach, enjoy some outdoor time on a private patio or balcony. Choose a premium unit for stainless steel appliances, double ovens, flat-screen TVs, and more.

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Contact us today to book your Labor Day Siesta Key getaway and make memories to last a lifetime!