The warmth and sun of Florida are a major attraction any time of year. Anticipate the cooling weather and return of fall and spend a little extra time in the sun and warmth with a trip to the Sunshine State’s fun and sun you won’t soon forget by heading to Siesta Key. Pack your bags and prepare for fun in the sun, water, and even on land as you check out many of the exciting activities there are to do and see while you cherish the last days of summer on your Siesta Key Labor Day weekend.
Beach Time
An island vacation, no matter what time of year you’re here, without a visit to its beaches is virtually unheard of. You and your loved ones are only moments away from the luscious sand and vibrant waters of the Gulf of Mexico no matter where you are on the island. Fill the cooler, pack the beach gear, and stake your territory with blankets and umbrellas as you prepare for a day of lounging on the shore, or a dip in the Gulf.
Snorkeling
Snorkeling is a great way to get in the water and explore the area, especially on the islands. Whether you rent gear from a local shop and explore on your own or book a charter tour, it’s a magical way to see the underwater world that surrounds Siesta Key this Labor Day. Adventurers looking to make their own fun should try Point of Rocks, a spot known for tide pools, moss-covered rocks, and sea life in an easily navigable and somewhat shallow area. If you’re looking for a group vibe, charter a boat with Key Life Charters where you can bring your own snacks, including adult beverages. Expand your snorkeling adventure by adding experiences like sightseeing, dolphin and wildlife spotting, and more for your unique and perfect trip.
Parasailing
Sail high over the water and gain a whole new perspective on where you’ve chosen to spend your Labor Day getaway with Parasail Siesta. You’ll take off from the deck of their specially designed and USCG-approved parasailing boat to fly high above the waters of the Gulf – up to 500 feet in the air! Keep watch on the water from your bird’s eye view for dolphins, turtles, manatees, stingrays, and other sea life. Stay dry throughout the flight or wear your bathing suit for a refreshing dip in the water before flying up again and coming down safely on the deck. Bring your waterproof or disposable camera to capture the memories from your perspective in the harness. Parasail Siesta takes several professional digital camera pictures of your flight and will provide you with a memory card at the end of the trip so you can develop your pictures whenever you like. Rides are approximately 15 minutes of airtime, but the whole excursion duration depends on the number of fliers.
Private Cruise
There are plenty of boat charter companies that offer cruises. Stay out of the cooling waters of the Gulf while still enjoying marine activity. Watch the sunset, search for dolphins and other marine life like manatees and aquatic birds, or just sit back and relax as the captain steers through the sea. Sip on an adult or other beverage as you take in the beautiful Florida coast and Gulf waters with your loved ones for a great way to end any day of your stay. Daytime and sunset cruises are available.
Bicycle Rentals
Siesta Key has a land area of just 2.4 miles, so there are bound to be places to explore where your rental car just can’t reach. Instead of trying to see everything by car, get some exercise by exploring the many walking and biking trails that bring you closer to the sights inaccessible by car. Choose from single-seat bikes without gears (a.k.a. cruisers), tricycles for extra balance and basket space, children’s bikes, adult bikes with baby seats, or choose to take a romantic ride on a bicycle-built-for-two – there’s a bike to fit the needs of everyone in your group! Ask about locks and extra baskets as well as safety gear like lights and helmets, and even perks like delivery to your accommodations.
Labor Day Fun on Siesta Key
When you book your fun-filled getaway to Siesta Key, you won’t be hard-pressed to find activities to fill every minute of every day you’re here. Rent Siesta Key has a rental to fit your needs, from one-bedroom units all the way up to six bedrooms for a Labor Day reunion with friends or family. Fuel up for the day or bring the group together with a delicious home-cooked meal prepared in your unit’s fully equipped kitchen. When the day is done, relax in a private bedroom, or spread out in the open living area for a game, movie, or TV show together. When you’re not at the beach, enjoy some outdoor time on a private patio or balcony. Choose a premium unit for stainless steel appliances, double ovens, flat-screen TVs, and more.
Contact us today to book your Labor Day Siesta Key getaway and make memories to last a lifetime!
The year-round Florida sun and warmth make it an ideal destination any time of year, but add the red, white, and blue, of the 4th of July and you can prepare for even more fun. Gather your loved ones and pack your bags with your most patriotic possessions for a fun and exciting vacation and an island-style 4th of July. Then set your sights on the keys and the many fun and unique offerings you’ll find there that will have you building a vacation that keeps everyone happy and busy and provides memories to last a lifetime.
Siesta Key Fireworks
Celebrate the 4th with fun and fireworks. The show is located off the shores of Siesta Beach, just north of the volleyball courts, but there are plenty of other great vantage points like Crescent Beach, the Public Beach, or you can even board a vessel and head out into the waters of the Gulf of Mexico or the Intracoastal Waterway. The free, family-friendly show takes place July 4th at dusk. Pets and personal fireworks should be left at home.
Beaches
While you’ll have to wait until the sun goes down to enjoy a fireworks display, the beaches of Siesta Key are open all day. Pack your beach gear and stake your claim on the beach for a day of sun, sand, and fun every day of your trip. Gather your group, your beach chairs, and sand toys and head to the Siesta Key Beach July 4th for a swim in the Gulf, or just to work on your tan. To make the day more festive, wear your red, white, and blue, pack a picnic lunch, and celebrate independence, island-style.
Island Hopping
Siesta Key’s size – it’s only 2.4 square miles of land – means there’s not a lot of room for a large-scale 4th of July event. You can get your fill of patriotic events when you do a little island hopping. Longboat Key, Bradenton Beach, and Anna Maria Island are all hosting large 4th of July events, many of which include parades, fireworks, cookouts, and plenty of patriotic fun. The Sarasota P1 Offshore Boat Races take place off of the shores of Lido Key July 1st – 3rd. Mainland Sarasota is also going all-out for the holiday.
Trolley
Hop on the trolley, which may be showing its best red, white, and blue décor, for a visit to the many businesses and sites along its route. Save the gas in your rental car for an off-island trip, conserve your own energy and spare the bike ride or walk between destinations for the fun you’ll have at your destination when you take the Siesta Breeze Trolley. Check out boutiques, shops, and restaurants. Many will be decorated in red, white, and blue for the patriotic holiday, and some even offer special events, discounts, and menus to mark the country’s independence. Experience fun, free, round-trip service from Siesta Key Village all the way to the southernmost part of the island, with many stops in between.
Other Activities
There are plenty of activities to keep you busy on your island respite this 4th of July. Many businesses will be decked out in red, white, and blue, and may even be offering special patriotic-themed services. Take a cruise through the water surrounding Siesta Key and try to spot dolphins, manatees, rays, and more. Keep the water activities going with SCUBA diving and snorkeling, paddleboarding, kayaking, or just going for a swim in the waves with loved ones. Florida is known for its world-class fishing, so get yourself a Florida fishing license and head out on an adventure. Take to the skies with a parasailing experience, stick to shore with an electric bike tour, or pamper yourself with a massage or facial at a spa.
Fourth of July Fun in the Florida Keys
When you book your 4th of July getaway with Rent Siesta Key, you won’t be short on fun and patriotic activities to fill your time while you’re here. You’ll be able to design a getaway that is uniquely yours with memories to last a lifetime. Relax and unwind in a private home after a fun-filled day. Enjoy a one-bedroom for your small family, all the way up to six bedrooms for a larger group red, white, and blue reunion. For more privacy, choose a single-family home with a garage. Make a group meal in your unit’s fully equipped kitchen, many including stainless steel, and high-end appliances. Enjoy the meal in the dining area, or in a private outdoor space like a patio or balcony. At the end of the day, relax in a private bedroom, or gather the group for a TV show or movie. Opt for a premium unit which may include perks like a fireplace, double ovens, flat-screen TVs, or a private pool. Include everyone by asking about select rentals that allow your fur babies to stay.
Contact us today to book your 4th of July getaway to Siesta Key!
There are many area attractions, shops, restaurants, and activities to keep everyone busy throughout a stay in Siesta Key. Add some holiday flair to your stay when you check out the many Easter activities that join year-round activities and attractions, you’ll want to make part of your Easter respite.
Easter Services
Siesta Key and the surrounding area have several churches where you can attend services while on vacation. Many will be holding special Easter services, including sunrise services, to mark the day. Contact your choice of church and inquire about dates, times, and locations for services.
Easter Brunch
Whether you attend church services or not, a traditional Easter celebration is brunch. Select restaurants in and around Siesta Key will be serving the traditional Easter meal of ham and all the fixings that go with it. Contact your restaurant of choice and ask about reservations, as well as the availability of pick up or delivery if you don’t want to brave the crowds.
Siesta Key Easter Egg Hunt & Games
While you’re on a trip to Siesta Key make sure you include plenty of Easter fun. The Annual Siesta Key Easter Egg Hunt will take place on April 16th from 9 AM – 12 PM. There will be a myriad of games and prizes, photos with the Easter bunny, Sherriff’s mounted patrol, a coloring station, and delicious Kona Ice available for purchase along with the hunt. Registration is required and there is a fee for $10 per child and is only available for children ages one through six. Each child who pre-registers will receive a festive Easter goodie bag! Each child should bring their own basket or tote for collecting eggs during the Easter egg hunt.
Sunset Tours and Dolphin Tours
Board one of the boats that Fun Boat has in their fleet and get started on one of the cruises that they offer! The dolphins and donuts cruise is offered in the mornings, lasts about 2 hours, and includes donuts and coffee. The dolphins and drinks cruise is offered midday, also lasts about 2 hours, and includes wine, beer, and water. Both of these cruises focus on finding dolphins as well as manatees (seasonal), a variety of aquatic birds, and other animals in the area so you can see more than just the Easter Bunny this Easter! Fun Boat also offers a Sunset Cruise that leaves an hour and a half before sunset. This cruise will make you realize why they call themselves Fun Boat! There will be complimentary wine and beer as well as a karaoke contest. Still keep your eye out for dolphins and all the other animals around!
Sarasota Art Museum
Travel a town away from Siesta Key to Sarasota to learn about contemporary art through several boundary pushing, thought-provoking exhibits, and guided tours that take you into the thick of it all. The museum includes a mix of permanent and temporary exhibits including Danner Washburn, Judith, Linhares, and more. Wander the Barbara Banks exhibit and learn about the workers that helped create this and many other buildings in the area throughout the decades and even centuries. Enjoy one of the many programs that cycle through the museum. These programs include artist talks, spotlight talks, free activities, and a variety of performances. You won’t want to miss out on the variety of things you can do and see at the Sarasota Art Museum while you’re here in Siesta Keys this upcoming Easter!
Siesta Key Rum
Adults will love visiting Siesta Key’s distillery. Enjoy a tour, tasting, and pick your favorites to enjoy back at your vacation rental. Choose from a variety of rums, gin, vodka, and whiskey, some with hints of toasted coconut, coffee, or spiced. Also try out our make a drink option! While their rums are smooth enough to drink on their own, they also make for a great base for cocktails!
Siesta Key Easter Excitement
You came to Siesta Key to explore and experience a fun, relaxing getaway this Easter with loved ones. Before you plot out your Easter fun in the area, make sure to book a vacation rental provided by Rent Siesta Key. We have units as small as one bedroom for a small family or sweetheart getaway, all the way up to seven bedrooms for a large family or group reunion this Easter!
You’ll have access to private outdoor spaces like a pool, balcony, or deck. Relax indoors in stylish bedrooms. Make a meal or host the elaborate holiday dinner in the fully equipped kitchen, then spread out in an open living area. For a luxury stay like no other, choose a premium unit to include perks like wood floors, flat-screen TVs, an elevator and more to make the stay one you’ll never forget.
Contact us today to start planning a fun-filled visit to Siesta Key!
The warmth and sun of Florida is a major attraction any time of year. The destination of Siesta Key is one full of plenty of Siesta Key Christmas cheer, along with the warm weather and salty sea air of the Gulf of Mexico. Enjoy whiling away the time on a warm, sunny getaway, but make sure to experience some of the Christmas cheer, fun, and excitement when you plan a winter break around the most wonderful time of the year.
Selby Gardens Lights in Bloom
Enjoy plenty of holiday cheer – and lights – with your island Siesta Key Christmas. Selby Gardens in downtown Sarasota will be hosting its annual Lights in Bloom: An Open-air Holiday Light Show. It features over two million lights strung throughout the gardens, including walkways, foliage, and all the nooks and crannies of the gardens. Make sure to bring your camera for plenty of photo opportunities! The family-friendly event also includes a children’s arts and crafts section, food, drinks, entertainment, and other activities to keep you busy.
Sarasota Christmas Glow Run
If you arrive for your Christmas island adventure early, get prepared for your big meal with a little exercise. Head to Sarasota to take part in their annual 5K run. Run or walk to the sounds of Christmas music along a lakeside course decorated with Christmas cheer. If you happen to miss the snow of colder climates, there is a 100% chance of snow at the finish line! The event takes place at Nathan Benderson Park in Sarasota on December 18 from 6-8 p.m. The event is free and includes a tank or tech tee, finish medal, finish video, and snacks. Nathan Bederson Park charges $5 cash for parking.
Siesta Key Village
Get your last-minute holiday shopping done, enjoy delicious food, or just take in the Christmas cheer as you explore Siesta Key Village. The area is the perfect place to explore on foot or by bicycle so you can visit all the nooks and crannies of the island where rental cars can’t go.
Sarasota Christmas Boat Parade
Grab a seat on the shores of Siesta Key between Centennial Park and Bayfront Park for a Christmas parade through water rather than snow. Whether the vessel is a small motorboat or a giant yacht, there’s a place in the parade for it. Captains and their crew decorate their vessels with plenty of Christmas cheer and blast live or recorded Christmas tunes from aboard. Several of Siesta Key’s beachfront restaurants with outdoor dining have great views of the water and the parade – and you can enjoy great food and drinks while you’re there! This year’s parade is December 11.
Christmas Church Services
Celebrate “the reason for the season” at one of Siesta Key’s churches. Several area churches will be hosting Christmas Eve and Christmas Day services to attend. Some may even be holding beachfront services.
Santa Stumble Pub Crawl
The adults-only event takes place the day after Christmas. Hosted by the Block that Roxx in Siesta Key Village, the crawl features stops at SKOB, Gilligan’s Island Bar, Daiquiri Deck, and 3.14 Pi. The event runs from 9 p.m. – closing time at the establishments. More details will be available soon.
Choose Your Own Adventure
Don’t forget you came to Siesta Key to rest and relax in the Florida sun as well as to celebrate the Christmas season with plenty of island cheer. There are plenty of indoor and outdoor activities that don’t necessarily have a jolly theme. Gather your group and head to the beach for some time in the sun, stand up paddleboarding, sandcastle building, and just about any other beach activity you can think of! Get out to some of the indoor attractions like escape rooms, museums, galleries, restaurants, shopping and an endless number of other activities. You can also choose to decorate your rental with removable, non-damaging decorations or create a Christmas-themed scavenger hunt or other activity that keeps you closer to home and away from the larger crowds of official events.
Siesta Key Christmas
When you book your Christmastime getaway to Siesta Key, you won’t be hard-pressed to find something to fill every minute of every day of your trip. Fuel up for the day or create a delicious home-cooked holiday meal prepared in your unit’s fully equipped kitchen. When the jolly fun is done for the day, relax in a private bedroom, or spread out in the open living area for a game, or to watch your favorite Christmas movie or a TV show. When you’re not at the beach or soaking up the Christmas cheer, enjoy some outdoor time on a private patio or balcony. Choose a premium unit for stainless steel appliances, double ovens, flat-screen TVs, and more. Rent Siesta Key has a rental to fit your needs, from one-bedroom units for your small family or Christmas romantic getaway all the way up to six bedrooms for a merry reunion with friends or family.
Contact us today to book your Christmas getaway and make memories to last a lifetime!
Fun, sun, sand, and warm temperatures year-round make Florida one of the best spots for a getaway any time of year. If you’re looking for all of that along with a bit of Thanksgiving flair, you’ll find everything you’re looking for in Siesta Key. There are plenty of events and activities, including the Siesta Key Thanksgiving Day dinner, to keep you busy throughout your stay.
Thanksgiving Dinner
While some of the restaurants on Siesta Key may be closed on Thanksgiving Day, there are several in and around the area that keep their doors open to serve traditional Thanksgiving meals. If your chosen restaurant isn’t open for service on Thanksgiving Day, ask about catering or delivery or take out that you can heat and serve at your rental.
Sand Sculpting Festival
If you’re taking an extra-long break this November, make sure your time on Siesta Key includes Thanksgiving as well as this November tradition. Each November, Siesta Key hosts the International Sand Sculpting Festival. These are not your average sand castle built with a pail and a bucket at the water’s edge. From large, intricate castles with carved details like windows, doors, and towers, to life-size replicas of famous people, sculptors from all over the world go all-out to showcase their skills and talent. This year’s festival is November 12-15. You can buy tickets for the event on their website. Want to showcase your own skills? Amateurs from kids ages 10+ to adults can register for the amateur competition on November 13. Registration for the amateur competition is November 9th.
Beaches
Make your Thanksgiving visit to Siesta Key complete with some beach time. While the water may be a little cool, you can still spread out on the sand and soak up the sun, talk a walk on the beach, or pack a picnic lunch. Create your Siesta Key Thanksgiving meal in your rental and bring it down to the waterfront to enjoy or pack a basket of leftovers for sandwiches and other beach snacks. Grab some sand toys and work on your skills so you can enter the Sand Sculpting Festival next year.
Bicycle Rentals
Keep the rental car parked at your accommodations and gather the group for some exercise after all the turkey. There are many walking and biking trails that take you to all the nooks and crannies of Siesta Key where your motor vehicle just can’t go. Many bike rental companies offer an array of options, from single-seat bikes with or without gears, adult-size tricycles for added basket space and balance, romantic bicycles built for two, children’s bikes, and adult bikes outfitted with baby seats. Make sure to ask about locks, extra baskets, and other accessories and safety gear like lights and helmets. There may even be perks like delivery to your accommodations.
Hiking
Stroll the streets of Siesta Key or hike its beautiful trails. Fall is one of the best times for hiking, as the weather is cooling down but still warm enough to keep you comfortable. Explore everywhere your feet can take you that your rental car can’t. Dress in layers and pack your essentials – like water, sun gear, and whatever else you need, and set out on an adventure. Make sure one of those essentials is your camera, as you’re bound to spot some of the island’s wildlife and capture breathtaking ocean views while you’re out.
Trolley
After you’ve walked, hiked, or biked your way around Siesta Key, there’s one more mode of transportation to try. Hop on the free trolley for a different type of transportation on wheels. Save the gas in your rental car for an off-island trip, and conserve your own energy for the fun you’ll have at your destination when you take the Siesta Breeze Trolley. It goes to just about any destination on the island! Experience the fun, free, round-trip service from Siesta Key Village all the way to the southernmost part of the island, with many stops at or near restaurants or shops in between. Get on or off at any stop and spend as long as you like at the location before meeting the trolley at another stop or when it comes back your way.
Siesta Key Thanksgiving with Family
When you book a Thanksgiving getaway with Rent Siesta Key, you won’t be short on fun activities to fill your time while you’re here. You’ll be able to design a getaway that is uniquely yours with memories to last a lifetime. Relax and unwind after a fun-filled day with your group. Enjoy a one-bedroom for your small family or sweetheart getaway, all the way up to six bedrooms for a larger group or Thanksgiving reunion. For more privacy, choose a single-family home with a garage. Make a delicious traditional Thanksgiving meal in your unit’s fully equipped kitchen. Enjoy the meal in the dining area, or in a private outdoor space like a patio or balcony. At the end of the day, relax in a private bedroom, or gather the group for a TV show or movie. Opt for a premium unit for perks like a fireplace, double ovens, stainless steel appliances, flat-screen TVs, a private pool, and more. Include everyone this Thanksgiving by asking about select rentals that allow your fur babies to stay.
Contact us today to book your Siesta Key Thanksgiving getaway!
The warmth and sun of Florida is a major attraction any time of year. Lounging in the sun or splashing around in the water of the Gulf of Mexico is a fun and relaxing way to while away the time on a Florida getaway, but you’ll want to make sure to experience some of the Siesta Key Halloween fun and excitement when you plan a fall break around one of the spookiest days of the year.
Siesta Key Safe Treats
Trick or Treat on Siesta Key is safe and fun, thanks to the Siesta Key Chamber of Commerce. The 37th annual Safe Treats for Kids is an event where merchants across the island will be handing out sweets and treats to costumed children. The afternoon event is a fun, relaxed event and the free Siesta Key Breeze Trolley can help you get between Siesta Key Village and Turtle Beach so you can maximize the fun. The free event is Saturday, October 30 from 1-4 p.m. at participating businesses across the island.
Sarasota Dog-O-Ween Costume Contest
If your furry friend made the trip with you, grab the leash and your fur baby’s costume and head to the Sarasota Annual Dog-O-Ween costume contest. Humans bring their canine companions to Paul Thorpe Park for some Siesta Key Halloween fun at the Sarasota Farmers Market Halloween Festival. Canines dress in their howl-o-ween best to compete for prizes including a complimentary exam donated by the Animal Medical Clinic at Rosemary, a gift basket full of toys donated by New Barker Magazine, and a $50 cash prize donated by the Sarasota Downtown Enrichment Association. The contest is Saturday, October 30. Registration is from 9-9:45 a.m. and the costume contest starts at 10 a.m. The cost is $5, and proceeds benefit the Donte’s Den Foundation. Keep in mind contestants must be leashed at all times and no retractable leashes are allowed. Make sure your dog visits the potty before the contest starts!
Ghost Stories & Tours at The Point
You’ll have to take a short trip to the mainland for this ghostly fun. Marie Selby Botanical Gardens historic Spanish Point campus in Osprey is leading spooky stories and ghost tours at Spanish Point. Take a tour led by storytellers as they reveal the spookier history of the Spanish Point campus. Tours take place from 7:30-9 p.m. October 28-30. Admission is $15 for all Selby Gardens members and $20 for non-members. Guests must be 8 years old or older to participate.
The Monsters Cruise
An adults-only party, the Monsters Cruise invites all witches, ghouls, zombies, monsters, and other scary spirits aboard the LeBarge. There will be a full bar and snacks available throughout the night for purchase aboard the vessel. Come in your Halloween best. There will be plenty of adults-only Halloween fun on board, including a drag show. The cruise sets sail Saturday, October 30 and sails from 9-11 p.m. This event is for guests 21 years old and up. If you don’t want the fun to end, look for other events at local restaurants and bars that take place before or after the cruise.
Choose Your Own Adventure
Don’t forget you came to Siesta Key to rest and relax in the Florida sun as well as to have some Halloween fun. There are plenty of indoor and outdoor activities that don’t necessarily have a spooky theme. Gather your group and head to the beach for swimming, stand-up paddleboarding, sandcastle building, and more. Get out to some of the indoor attractions like escape rooms, museums, galleries, restaurants, shopping and an endless number of other activities. You can also choose to decorate your rental with removable, non-damaging decorations or create a Halloween-themed scavenger hunt or other activity that keeps you closer to home and away from the larger crowds of official events.
Siesta Key Halloween
When you book your spooktacular Halloween getaway to Siesta Key, you won’t be hard pressed to find something to fill every minute of every day of your trip. Fuel up for the day or bring the group together with a delicious home-cooked meal prepared in your unit’s fully equipped kitchen. When the spooky fun is done for the day, relax in a private bedroom, or spread out in the open living area for a game, movie, or TV show. When you’re not at the beach or soaking up the Halloween fun, enjoy some outdoor time on a private patio or balcony. Choose a premium unit for stainless steel appliances, double ovens, flat screen TVs, and more. Rent Siesta Key has a rental to fit your needs, from one-bedroom units for your small family or spookily romantic getaway all the way up to six bedrooms for a Halloween reunion with friends or family.
Contact us today to book your Halloween getaway and make memories to last a lifetime!