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Best Places To Stay In Florida: Siesta Key Holiday Guide

     Welcome to the No.1 website for luxury vacation rentals in Siesta Key, Florida. Home to some of the best beaches in the world, Siesta Key is a beautiful island retreat popular with families, couples and groups who want a refreshing beach break. Close to Sarasota, you'll find a spectacular coastline boasting beaming white sand and turquoise waters as well as plenty to do.


     Here's our guide to all the best things to do and see in Siesta Key, from the best beaches to the best attractions and restaurants, read on to plan your perfect Florida beach getaway.

     Located in the Gulf of Mexico not far from Sarasota in south west Florida, Siesta Key is a barrier island with beaches rated the best in the US and the world.


All the best,

John Paul Donnelly

     P.S Picture This..Creating Magical Memories with Your Friends and Family Whilst Staying in a Luxury Siesta Key Vacation Rental.

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Why choose Siesta Key, Florida?

     You can choose to stay on the island and enjoy a relaxed beach holiday with lazy days on the beach, topped with fun evenings at the many bars and club. Alternatively you can mix things up with trips across to nearby Sarasota or even Tampa which is an hour's drive away.

      The beach is what people come for and it doesn't disappoint. A composition of 99% quartz delivers fine, soft sparkling white sand that stays cool despite the heat. Edged by palm trees with calm waters and breathtaking sunsets, it's easy to see why these tropical beaches are so special.

     Despite their world class status, Siesta Key's many beaches don't feel overcrowded or too busy because there's plenty of shoreline to choose from. You'll also find lots of watersports to keep you occupied as well as boat trips, dolphin tours and sunset cruises.

      Between Siesta Key Village and St. Armand's Circle there are plenty of shops, galleries, restaurants, spas, golf clubs, resorts, bars and nightclubs to keep you entertained. If you want more attractions or restaurants you can always pop over to nearby Sarasota or even Tampa which is only an hour's drive away.

     You'll discover lots of superb places to stay in Siesta Key with a great choice of luxury beachfront vacation rentals and villas by the water's edge. Delivering dream coastal views, private pools and top facilities these are perfect vacation rentals for families, couples and groups.

      For a relaxing Florida beach retreat, Siesta Key delivers all the sun, sea and sand you need in the perfect place to unwind.

Browse luxury Siesta Key vacation rentals

Best things to do in Siesta Key, Florida

      Read on for all the best beaches, restaurants and attractions in Siesta Key.

Best things to do in Siesta Key:

     You've come to experience one of the best beaches in the world so head over to Siesta Key Beach. Siesta Beach has been awarded the title of America's best beach a number of times in recent years.

     In addition to miles of super soft white sand you'll also find a playground, volleyball courts, tennis courts and a fitness trail on Siesta Key Beach. Just before sundown head to Sunset point to watch the sunset from the best place on the island.

Crescent Beach

     For quieter shores and the best diving on the island, hop over to Crescent Beach where you can enjoy the beauty of Siesta Key in peace on a more exclusive stretch of sand popular for beachfront vacation rentals.

Point of Rocks

     If you enjoy snorkelling and diving, Point of Rocks is the best place to dive on Siesta Beach. You'll have a great time spotting all the little fishes as well as crabs and other small marine life in the clear waters.

Turtle Beach

     If you do happen to tire of the gleaming beaches or miss hunting through the sand for shells, check out Turtle Beach. The sand on Turtle beach has a more familiar colour with larger grains of sand, often hiding the odd shark's tooth dragged in from tropical waters. The water here is much deeper and you'll also find volleyball courts and a playground alongside the beach.

     The are tons of watersports for everyone to enjoy, including jet skiing, banana boats, kayaking, paddle boarding and parasailing. The waters surrounding the beach are home to dolphins, manatees and lots of marine wildlife so it's worth taking a boat cruise to see dolphins leaping out of the water.

Siesta Key Drum Circle

      Don't miss the chance to experience a Siesta Key Drum Circle on a Sunday evening just before sunset. It's a beautiful hour of dancing and drumming where no matter whether you're a tourist or a local, you can push inhibitions to one side and get loose on the sand alongside belly dancers, fire eaters and more.

Beer Can Island

     For a beach in a more rustic setting, visit Beer Can Island where you'll find coves in their natural setting with the same soft white sand. Here you can tie your hammock between the trees and lie in the most tranquil setting away from the crowds.

Circus Sarasota

      Take a trip to Circus Sarasota to see thrilling performances by the historic Circus Arts Conservatory. On another day you can challenge everyone to find their way through the labyrinth in the courtyard at St. Boniface Church which was inspired by the labyrinth at France's Chartes Cathedral.

     For something completely different, Tampa is only an hour's drive away and Orlando a mere two.

Best restaurants in Siesta Key, Florida

     The cuisine you'll find at Siesta Key is a reflection of its position in the Gulf of Mexico. Drawing inspiration from South America and the Caribbean as well as its island location, you'll find everything from Mexican to Peruvian fusion, fresh seafood, Italian and Jamaican.

The Cottage Restaurant

      The Cottage Restaurant and Javier's Restaurant are both top Siesta Key restaurants that feature Peruvian-inspired dishes. For traditional flavours head to Javier's Restaurant where you'll discover authentic Peruvian fare or for something more contemporary, The Cottage Restaurant serves fantastic Peruvian-fusion dishes.

Captain Curt's Crab and Oyster Bar

     Enjoy freshly caught local seafood and live music at Captain Curt's Crab and Oyster Bar or try Clayton's Siesta Grill. Alternatively, feast on flavourful Caribbean and South American cuisine at Senor Siesta Restaurant or Mexican at The Hub Baja Grill.

     Italian fine dining doesn't get any better than Cafe Gabbiano whilst wood fired pizza at Flavio's is a must. For a local favourite head to Sun Garden Cafe for delicious American-style dishes inspired by food from around the world.

Best places to stay in Siesta Key

      If you dream of a stunning beachfront vacation rental, Siesta Key is the perfect destination. You'll find a fantastic choice of luxury vacation rentals to suit every need.

     From house rentals to condos, pet -friendly holiday rentals, villas with private pools and holiday rentals with dramatic sea views, you'll find a top accommodation with all the superb facilities you want.

     Whether you need a Siesta Key holiday rental for a couple, family or group, you'll find the perfect holiday home to suit your needs. Here are our top picks of the best places to stay in Siesta Key:

Discover more luxury Siesta Key vacation rentals

or call us to discuss the best luxury holiday rentals in Siesta Key to suit you and your family

Holidays in Siesta Key: Why go?

     Find out more about the top attractions in Siesta Key:

Nearest airport to Siesta Key

      The nearest airport to Siesta Key is Sarasota Airport alternatively Tampa Airport is only an hour's drive away.

When is the best time to visit Siesta Key?

     The best time to visit Siesta Key if you want to enjoy the warmest weather and the area at its best is in the summer months. Siesta Key is extremely popular so the summer is very busy and of course, schools are on holiday so you expect crowds although the beaches are never overcrowded. Temperatures can reach as high as 32°C during the summer.

     If you want to visit Siesta Key at a quieter time, mid March to May and September to October are less busy with lower temperatures.


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In 2005, John Paul Donnelly, began his luxury villa journey. He spent three years building resorts and holiday apartments in Alanya, Turkey, along with his brother, Joe. The concept was to create the most luxurious villas on the Turkish coastline and provide clients, along with their family and friends, the opportunity to enjoy exclusive holidays together.

By 2008, after the successful development of 3 resorts, JP had well and truly fallen into the world of villa rentals. With a portfolio of 6 villas and a desire to explore new places, he decided it was time to take the villa rental business outside of Turkey. He wanted to give his clients access to beautiful holiday rentals in destinations across the globe.

The expanding villa rental company was rebranded in 2011 to 5 Star Villa Holidays, and today 5 Star Villa Holidays offers over 4,000 luxury villas around the world.

JP and his partner, Helena are currently travelling the globe, devoted to hand selecting the best villas and property management companies, and giving them their stamp of approval! 5 Star Villa Holidays' ambition goes beyond being an ordinary holiday rental company. It is a marketplace for luxurious and exclusive villas around the world.

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