First-Time Visitor’s Guide to Siesta Key

Siesta Key is a hidden gem for your next Florida vacation. While many flock to the tourist cities of Orlando, Tampa, or Miami, Siesta Key is a quieter spot perfect for families or a getaway with your sweetheart or best friends. If you’ve never visited Siesta Key, you may be wondering about some of the “can’t miss” destinations. Here is our complete guide for first-timers to the area.

Just minutes from downtown Sarasota, Siesta Key is a barrier island in the Gulf that is as convenient a travel destination as you could ever hope for. If you have to rent a car, you can leave it parked on the island because most people bike or walk from the restaurants, to the beaches, and back to their rental homes.

About Siesta Key

The heart of Siesta Key is known as The Village, which is a collection of shops, stores, restaurants, and bars. Finding a place to park in this area can be difficult in the busy season, but our homes are mostly within walking distance, so you don’t have to worry.

There’s even a grocery store, and the first trolley stop lets visitors on and off right out front. The further south you travel from the Village, the more condos and residential areas you’ll pass. But plenty of people like to ride the free trolley just for the experience and to visit all the other Siesta Key beaches.

Top Things to Do in Siesta Key

There are tons of activities in and around Siesta Key, but there are a few that you can’t leave without experiencing. One of the most fun and unique events is the weekly drum circle on Siesta Beach. Each Sunday, locals and tourists alike gather on the shores of Siesta Beach to listen to the drumbeats and dance the evening away. Show up about an hour before sunset, and stay after the music is over to witness the most picturesque view as the sun disappears past the horizon.

If you’re an animal lover, you’ll definitely want to book a charter or tour to get up close and personal with the sea life. C.B. Saltwater Outfitters offers snook fishing night expeditions, or you can go for a dolphin tour with companies like Siesta Key Watersports. You’re also likely to see wildlife like osprey, sharks, or even the elusive bald eagle or sea turtle!

Best Restaurants

Siesta Key has some of the freshest and most mouthwatering food in the area, so you’re sure to have a great meal no matter where you go. Most of the restaurants (and definitely the most popular) on Siesta Key are just steps from our vacation rental homes, so you never are out of options for any meal.

Restaurants You Can Walk To

Siesta Key Oyster Bar and Gilligan’s Island Bar and Grill are among 2 of the most popular hangout spots because of the great outdoor atmosphere and good choices of beach food. But the Lobster Pot, Bonjour French Cafe, Ripfire Pizza and BBQ, Another Broken Egg, and The Hub Baja Grill are all on the same street and just a block or two away.

Fine Dining That’s Worth It

If steak and seafood, are top of your list. We send people straight to Summer House because you won’t find a better selection. It is going to be on the higher end of price range, but it is going to be one of the best entrees of your life. For an upscale meal with an unforgettable view, Ophelia’s on the Bay in nearby Sarasota is the place to be. You’ll find innovative and fresh dishes that make you feel like you’re in the lap of luxury.

Plan Your Vacation

Siesta Key has something for everyone, and there’s so much to do, you just might have to make a return trip! Contact us today for more information on our Siesta Key vacation rentals and all the fun activities you can experience in the area.

Photo Credit @faithdaniellephoto

Most Popular Beaches

You can’t go on a Florida vacation without hitting the beach! The most popular spot on Siesta Key is Siesta Beach, which has been ranked “#1 Beach in America” on multiple occasions. The clean sand and clear water make for a gorgeous view, and amenities like a shaded playground and sports courts make it a fantastic stop for the whole family.

If you’re looking to collect shells or spot sea life, Crescent Beach is your go-to. This beach is a bit more secluded, but it’s worth the trip. The views are unbelievable any time of the year, and just beyond the beach, Point of Rocks is great for snorkeling and picking up seashells.

Where to Stay

Our Siesta Key vacation homes for rent provide the ultimate nesting space for your group. When the day is done, return to your rental for a private and comfortable area to unwind and spend quality time together. Our properties are curated with you in mind, so you won’t have to worry about a thing on your getaway. You’re close to the action while keeping your own private space, and the luxurious amenities and unique décor put the finishing touches on your experience.


Siesta Key Luxury Rental Properties
5111 Ocean Blvd. Suite B, C & D
Siesta Key, Florida USA 34242
#SiestaKeyLuxury #iHeartSiestaKey
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