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Siesta Key - 1,048 vacation rentals

Siesta Key

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This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

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Siesta Key Travel Tips

When you take a vacation to Siesta Key, Fla., you’ll find people who enjoy an active lifestyle. From artists and writers to outdoor sports enthusiasts, there’s much to do on this barrier island. At 8 miles long, you’ll find some of the world’s best white sand beaches, shopping and dining that will make you want to extend your vacation into a lifelong stay.

This little island of paradise is perfect for a romantic getaway or a family vacation. The clear waters will inspire you and the one-of-a-kind attractions are what you always imagined an island escape would be.

Must-see Attractions in Siesta Key

Beaches: When you go to Siesta Key, it’ll be hard not to find yourself at Siesta Key Beach. The fine white sand is perfect for a day of fun in the sun and the water is even better for activities like surfing, wakeboarding and boating. This beach is one of the most beautiful in the country, so you certainly don’t want to skip it. There are several other beaches on the island as well, including Nokomis Public Beach, North Jetty Park Beach, Whitney Beach, Palma Sola South and North, Englewood Mid Beach and Palm Island North.

Beach rides: If you’ve always wanted to take a cruise along the beach, Siesta Key is the place to do it. There are several local companies that offer rides to visitors and guests, and they will guide you along the shores in covered golf carts to give you some of the best views you can find.

Point of Rocks: You haven’t seen anything until you visit Point of Rocks. This beach is a rare geologic feature that’s perfect for bird watching and marine wildlife viewing. On top of that, there’s a scenic beach nearby for you to watch the sunset and enjoy the scenery. Fishermen will love Point of Rocks as they cast out their lines and try to snag a bite.

Outdoor activities: There’s a reason many of Siesta Key’s residents enjoy outdoor activities - there’s so much to do! Whether it’s getting a tan on the beach or dipping your toes in the water, a relaxed lifestyle is what it’s all about. Guests can go fishing along one of the many piers, including the Englewood Ken Thompson Park Pier and the New Pass Pier. You can even watch a game of cricket and learn more about this English pastime with a visit to the Sarasota International Cricket Club’s grounds. During the summer months, visitors can check out free concerts in the park to hear a number of musical performances and get down. You can also go wind surfing, jet or water skiing, boating and snorkeling if you want to get up close and personal with the water and take on a more daring adventure.

Shopping and Dining in Siesta Key

Shopping: There’s plenty of shopping to be done in Siesta Key and the surrounding areas. The island is just a short drive from Sarasota, which has the sophistication of a big city but remains full of small-town charm. If you want to stay on the island, there are a number of shops at Siesta Village, which is located at the north end of Siesta Key and just a short distance from Crescent and Siesta beaches. You can also find more than 100 shops, boutiques, galleries and sidewalk cafes at St. Armand’s Circle along Main Street and Palm Avenue in Sarasota. If you want, get up on a Saturday morning and head to Sarasota for the farmers market on Main and Lemon streets downtown. Aside from the fresh food and handmade goods, you’ll also find goodies for your pet.

Dining in Siesta Key: If you want to take in views of the water while dining, head to Marina Jack’s on Sarasota’s bayfront. There’s also O’Leary’s Tiki Bar at Centennial Park along Sarasota Bay which is a great place for travelers who want to enjoy a good vibe and socialize. You’ll find plenty of places to choose from in downtown Sarasota along Main Street. There are eateries and bars, including Mattison’s City Grill as well as Divino Restaurant, where you will find tasty food and impressive live entertainment.

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