Holiday Search

Siesta and Longboat Key Holidays

For unparalleled sandy beaches and glorious, sapphire-blue seas, a holiday in Siesta and Longboat Key is a picture-postcard perfect destination for beach lovers everywhere. Besides award-winning beaches, there are a whole host of cultural activities, high-quality restaurants and a renowned laid-back atmosphere for visitors to enjoy. So kick off you shoes and feel the warm sand between your toes at this stunning Florida location.

Siesta & Longboat Key Hotels

Travel Guide

Colony Beach & Tennis Resort

Colony Beach & Tennis Resort

Ideally located on a spectacular off-shore island, the Colony Beach & Tennis Resort has a host of excellent facilities including three restaurants and a swimming pool. It is also a terrific tennis resort.

  • Family Friendly
  • Great Location
  • Swimming Pool
View hotel

The Resort at Longboat Key Club

The Resort at Longboat Key Club

Flight & Hotel

7 nights from
Adult £780

The Resort at Longboat Key Club is a luxury 4-star resort with six restaurants, a heated pool, an outstanding tennis club and a beautiful exclusive private beach.

7 nights from Adult £780 Child £617

  • Family Friendly
  • Kids' Activities
  • Swimming Pool
View hotel

Flight & Hotel

7 nights from
Adult £780 Child £617

View hotel

Luxury Holidays in Siesta and Longboat Key

We at Kenwood Travel will make your Siesta and Longboat Key holidays the rejuvenating endeavour you seek by putting you up in the most exclusive and luxurious resorts. In Longboat and Siesta Key you’ll find all the pleasures that a true hedonist dreams off. Bask in the sun, play a round of golf, enjoy a cocktail by sunset followed by a candlelight dinner; the pleasures are countless so escape to these islands and indulge! A holiday in Siesta and Longboat Key in Florida brings you to an elegant and scenic environment that is renowned for its luxury resorts, exclusive golf and tennis clubs as well as its fine dining and shopping. The breathtaking beaches and the numerous cultural activities, in combination with the relaxed and elegant lifestyle, make these destinations the holiday you’ve always dreamt of.

5 Great Reasons to Holiday in Siesta and Longboat Key

  • Siesta Key Beach is the nation’s best beach where you’ll find the world’s finest, whitest sand!
  • Shelling, biking, fishing, watersports and rollerblading; the fun activities are endless
  • Enjoy the exotic flowers, tropical trees, offshore dolphins and manatees, the scenery is mind-blowing!
  • Visit one of the tropical nature reserves!
  • Legend has it that Siesta Key’s Point of Rocks was often visited by pirates burying treasures

Things to do Whilst on Holiday 

Funky beach bars, intimate cafés, European-style pubs and live music venues make the nightlife incredibly exciting. These islands are also home to a thriving colony of artists and writers as well as a popular destination for celebrities since everybody enjoys the friendly and laid-back ambiance; so check it out for yourself!


A tropical savanna climate makes a holiday in Long Boat and Siesta Key possible all year round.

Interesting Facts About Siesta Key

  • Area – 3.5 sq miles
  • Population – 7,150
  • State – Florida
  • County – Sarasota

Interesting Facts About Long Boat Key

  • Area – 17 sq miles
  • Population – 7,603
  • State – Florida
  • County – Sarasota, Manatee

Siesta and Longboat Key Holidays 2017/2018

In order to avoid disappointment make sure to book your holiday for 2017/2018 early. Our 30 years of experience in the business makes us at Kenwood Travel your ideal partner if you are contemplating a holiday on Florida's Gulf Coast. So whether you seek a honeymoon, a family vacation or an all inclusive deal we have the knowledge to present you the tailor made package you fancy.

Other Florida Gulf Coast Locations

Other Florida Destinations

Your Holiday Details
Or why not personalise your trip?
Simply fill in your details below and use Additional Notes box to tell us any specific requirements or ideas you might have for you holiday. We'll get back to you and together we can plan a trip designed with you in mind.
Contact Details