Dine at nearby world-class restaurants, or spend your days shopping at the area’s best outlets. Visit some of the world’s finest beaches just moments away and relax in the Florida sun. So go ahead, start planning your next family adventure or business trip. A sunny and spectacular Siesta Key vacation awaits you.

Oct 4 - Apr 25, 2018 Phillippi Farmhouse Market

Phillippi Farmhouse Market returns for its 8th year on Wednesday, October 4th.

Oct 5 - Jul 29, 2018 Live Music at Sand Dollar Pool Bar

Join us outside every Friday, Saturday and Sunday for live music at the Sand Dollar Pool Bar every Friday, Saturday and Sunday.

Apr 13 - 22, 2018 Sarasota Film Festival

Celebrating its 20th anniversary this year, SFF has earned a strong, national reputation for bringing award-winning films and stars to Sarasota as well as partnering with the venerable Through Women's Eyes Film Festival.

Apr 21 - 22, 2018 Siesta Fiesta

Join us in Siesta Key Village this last weekend in April to peruse the largest arts and crafts show in our area all year.  Siesta Key Village on Ocean Blvd. Take Jonny's Original Free Ride from the hotel to avoid looking for a parking space.

Apr 27 - 29, 2018 FSRA Sweep Rowing Championships – April, 2018

2018 FSRA Sweep Rowing Championships held at Nathan Benderson Park is located just 10 miles from this Siesta Key Gateway property.    Reservations for your stay can be made by contacting our front desk: 800-930-4439.

May 5, 2018 Amateur Sand Sculpture Contest

Enter now to participate in one of the longest, running amateur competitions on Siesta Beach.  Hone your skills to participate in the competition during the Siesta Key Crystal Classic in November.

May 7, 2018 18th Annual Siesta Key Chamber Golf Tournament

Come and join the fun at TPC - a rare opportunity to play on this private members only course.  Your registration entitles you to lunch, dinner, golf balls and a round of golf on one of the most beautiful courses in our area.  Call Siesta Key Chamber for details - 941-349--3800.

May 20 - 27, 2018 The Oaks Club USTA $25,000 Women’s Tournament

The $25,000 Tennis Tournament returns to Osprey hosted by The Oaks Club.

Jun 5 - Aug 7, 2018 Kids Summer Beach Fun Runs

Every Tuesday evening, join the crowd for a fun run or walk from Siesta Beach to Point of Rocks.   Registration begins at 5:30 and race begins at 6:30.  Come join in on the fun!

Jul 4, 2018 4th of July Fireworks on Siesta Beach

Watch Siesta Beach and Zambelli light up the sky on the 4th of July at 9 PM.  Free to all.  A community event sponsored by the Siesta Key Chamber of Commerce.

Jul 19 - 24, 2018 USA Volleyball Championships

Siesta Key beach will once again play host to the USA Volleyball Beach Championships for 12U through 18U divisions.  Qualifying rounds begin in March.

Nov 9 - 12, 2018 9th Annual Siesta Key Crystal Classic

This spectacular festival, filled with so many things to do and see over the course of its 4 day life, comes alive on Friday, November 9th.

Nov 24 - 24, 2018 Siesta Key Light Up the Village

Join us in Siesta Key Village for this annual parade featuring the one and only Santa Claus.

Beach Shuttle Service

Jonny’s Original Free Ride provides shuttle service for hotel guests to all of Siesta Key including Turtle Beach and the Village. Make your arrangements with the front desk staff between 10am – 4pm.

Poolside Bar & Grill

Our latest addition is open seven days a week until 10pm with a daily happy hour from 3 – 6pm. Add to the nighttime ambiance with our beautiful fire pit, outdoor living area and renovated pool area.

100% Non-Smoking

One of our most-requested changes: you asked, we listened! Our property is now 100% non-smoking in all public areas. Rest easy knowing that the property is now completely smoke-free.

Association Discounts

We offer discounted rates for AAA/CAA and AARP members. Contact our front desk toll-free at (800) 930-4439 and ask for your special member rate. Member card must presented at check-in.