Please spend some time looking around our website.

We have gathered information about our world-class beaches, Siesta Key beach accommodations including our daily, weekly and seasonal vacation rentals, real estate, casual and fine dining, amazing seafood, shopping, community resources and more to help make your stay so memorable that, like many of our residents, you won't ever want to leave Siesta Key.

Siesta Key is a vibrant community with and there is always something going on here so whether you are looking for live music, yoga or Pilates on the beach, or a drum circle, make sure to check out our Events Calendar and have some fun with us.

Events Calendar

Siesta Key is a vibrant community and there is always something going on here so whether you are visiting us for a week or you are a lifelong resident of our beautiful island, make sure to check our events calendar and have some fun with us.

YMCA Tropical Splash
October 04, 2014
From: 6:00AM to 11:00AM

Tropical Splash Open Water Swim Competition

Siesta Beach. YMCA event, beach start

Saturday October 4th 6AM-11AM


For more info:

31st annual Siesta Key Triathalon Fundraiser
October 05, 2014
From: 6:00AM to 11:00AM

YMCA Sharks fundraiser, Sprint distance

31st annual Siesta Key Triathalon

Sunday October5, 6AM - 11AM

For more info:

Historic Spanish Point Scarecrow Festival
October 10, 2014
From: 9:00AM to 5:00PM

Scarecrow Festival - Friday Oct 10th & Saturday Oct 11th

9am - 5PM

Historic Spanish Point, 337 N. Tamiami Trail, Osprey FL.

Admission: Adults:$12 Seniors:$10 Children age 6-12:$5  Under 6:Free

Build a Scarecrow and enter the competition!!!

Join us Friday evening for the Sunset Scarecrow BBQ & Dancing to the Dan Dembicki Trio - Sponsored by Kay's BBQ

$45 members $55 non-members (includes admission) For tickets call  941-966-5214 ext. 2200


CB's Saltwater Outfitters "Orvis Fly Fishing 101" Clinic
October 18, 2014
From: 9:00AM to 11:00AM

CB’s Saltwater Outfitters “Orvis Fly Fishing 101” Clinic, Oct 18, 2014

CB’s Saltwater Outfitters, 1249 Stickney Pt. Rd., on Siesta Key (Sarasota) will hold an “Orvis Fly Fishing 101” clinic with Orvis-Endorsed fly fishing guides, Capt. Ed Hurst, Capt. Kelly Stilwell, Capt. Rick Grassett and Capt. Andy Cotton
Saturday, Oct 18 from 9am - 11am. 
Cost for the clinic is $20 and will include fly tackle rigging basics and fly casting.
There will also be special in store offers on Orvis products.
Call (941) 349-4400 to reserve your spot.

East End Volleyball Tournament
October 25, 2014
From: 9:00AM to 5:00PM

East End Volleyball Tournament: Volley America Tour

30 Courts

Saturday and Sunday 9AM-5PM at Siesta Public Beach

For more info:

2014 Halloween "Safe Treats" in Siesta Key Village
October 31, 2014
From: 3:00PM to 6:00PM

For the 29th year, the Siesta Key Village Association will once again host "Safe Treats" on October 31, 2014 from 3PM-6PM.

Bring your little ones to trick or treat in Siesta Village along Ocean Blvd. and the surrounding streets. Look for participating members displaying orange and black balloons and pumpkin flyers in their windows. This free event provides a safe venue for children on Halloween.

For more information visit the web site at or call Helene Hyland at 941 685-2274

Volleyball Dig It Tournament
November 01, 2014
From: 9:00AM to 5:00PM

Volleyball....Dig It Tournament

Saturday and Sunday, November 1st and 2nd 9AM-5PM

Siesta Key Beach

24th Annual Sandfest
November 07, 2014
From: 5:30PM to 10:00PM

24th Annual Siesta Key Chamber Sandfest dinner/dance under the pavillion at Siesta Beach with a spectacular Gulf sunset as a backdrop.

This year features a "Siesta Key Hoedown" theme so join us for some fun, food, music, and boot-scootin'!


For reservations or more info call (941) 349-3800 or visit

2014 Siesta Key Crystal Classic Master Sandsculpting Competition
November 14, 2014
From: 10:00AM to 5:30PM


On Siesta Key, recently named America's #1 Beach, the Crystal Classic has become a favorite of the professional sand sculptors who have competed here. Citing the beauty and cleanliness of the pristine white sand, sculptors have remarked that their sculptures look almost as if they were "carved in marble."

In only 24 sculpting hours, (spanning the four day event), the master sculptors create sand masterpieces, some over ten feet tall, and transform the always beautiful Siesta Beach into an outdoor art gallery. The Crystal Classic connects the arts and the beach in ways never before seen in Sarasota.

This event also includes a wonderful Vendor Village, Amateur Sandsculpting competition, live music, Sandsculpting demonstrations, and much, much more!

Go to for more information and schedule of events.

Siesta Key Annual Light Up The Village Parade and Open House
November 29, 2014
From: 6:00PM to 9:00PM

Annual Light Up The Village Parade And Open House - Nov 29th, 2014 from 6PM until 9PM

Siesta Santa 400 2014

Children can give Santa their wish list, have their face painted, visit with Santa's elves and be entertained by Sunshine the Clown. Santa's gift bags provided by Beach Bazaar will be given to the first 250 children who visit with Santa. Santa will arrive by fire truck following the parade at approximately 6:15 pm.

Businesses will provide refreshments, while you enjoy live musical entertainment by the Pine View High School Jazz Band, Keyboard Players and choirs singing holiday songs. Ocean Blvd. will be lined with luminaries and businesses will be decorated for the holiday season. Free Trolley Rides will be available from Siesta Key Public Beach to the Village from 5:30 pm - 10:00 pm.

38th Annual Sandy Claws 5K Run
December 13, 2014
From: 7:00AM to 11:00AM

Sandy Claws 5K Run on Siesta Beach, 948 Beach Road, Siesta Key 34242

Saturday, December 13 7AM-11AM

For more information:

Siesta Key Half Marathon 10K and 5K
December 14, 2014
From: 7:00AM to 12:00PM

Siesta Key Half Marathon

Sunday December 14 7AM-Noon

Multi-race event, running on streets, no roads closed.

For more information:

Siesta Village Valentine Stroll Feb 14, 2015 Everyone gets a kiss!! 5PM-8PM
February 14, 2015
From: 5:00PM to 8:00PM


The Siesta Key Village Association will be hosting the annual Siesta Key Village Valentine Stroll. Residents and visitors are invited to stroll through Siesta Village which will be adorned with Valentine cheer.

There will be something for everyone including live music throughout the Village and candy kisses will be distributed by the merchants.

Participating merchants will be displaying red and pink balloons outside their businesses.

Siesta Key Village offers romantic destinations for you and your sweetheart and lots of fun for the whole family. If parking is a concern, there will be a free Trolley service from the Siesta Public Beach parking lot to the Village from 4:30 to 8:30 PM compliments of Siesta Island Trolley and Daiquiri Deck.

15th Annual Siesta Key Easter Egg Hunt and Games- April 4 Ages 1-6
April 04, 2015
From: 9:00AM to 11:30AM

Saturday, April 4, 2015  9:00 am to 11:30 am For children ages 1-6

For Children Ages 1-6. Each child receives an Easter Stuffed Animal and an Easter Egg Hunt Goody Bag stuffed with prizes. 

Face painters will be there and opportunities to ride the trolley, tour the Siesta Key ambulance and fire truck and participate in other fun family entertainment. Sheriff Dept. fingerprinting kits are available. Registration is limited to first 125 paid children. For additional information contact Roz at 941-349-2770 ext: 227