Discover amazing Siesta Key activities and premium in-home experiences.
Siesta Key is a coastal destination in Florida Gulf Coast, where you'll find sun-soaked beach days, fun for families. Whether you're seeking relaxation, exploration, or local flavor, this vibrant spot has something for everyone.
Explore Siesta Key at your own pace with a street-legal golf cart rental.
Cruise Siesta Key’s waterways on a 2024 tiki boat with music, drinks and coastal wildlife views.
Soar above Florida's top-rated beach and spot dolphins during a 12–15 minute parasail flight.
Enjoy a relaxed evening cruise along Siesta Key with music, LED lights and possible dolphin sightings.
Explore pristine sandbars, collect shells, and relax on a fun 3-hour boat excursion
Watch playful dolphins and a vibrant Gulf sunset while enjoying complimentary beer and wine.
Enjoy a morning cruise with complimentary drinks while spotting dolphins in Siesta Key.
Soar above Siesta Key and spot dolphins on a safe, family-friendly 2.5-hour parasailing cruise
Spot playful dolphins and relax at a scenic sandbar while enjoying complimentary drinks
Ride new Yamaha jet skis across Florida's largest riding area at your own pace
Cruise Sarasota’s Gulf waters on a spacious pontoon with flexible 4- or 8-hour options.
Customize your day exploring sandbars, islands, and marine life on a private catamaran.
Bypass traffic and enjoy a Siesta Key sunset with convenient e-bike drop-off and pickup
Paddle through Jim Neville mangroves to a secluded beach accessible only by boat
Explore calm Turtle Beach waterways at your own pace with quality kayaks or paddleboards
Pedal effortlessly through Sarasota Bay and encounter vibrant marine life on a small-group guided adventure
Fish 11–14 miles offshore with gear, bait, and license included
Experience custom deep sea fishing with comfort and flexibility on a private charter.
Experience marine life up close on a comfortable pontoon cruise for all ages.
Savor Sarasota’s flavors and history in one unforgettable afternoon!
Explore Sarasota's historic neighborhoods and cultural landmarks on a 90-minute air-conditioned trolley ride.
Solve a circus-themed murder mystery on a rolling trolley with interactive fun and complimentary drinks.
Explore Venice's fossil-rich waters and hunt prehistoric shark teeth by snorkel, Huka, or scuba
Refresh your dive skills with tailored instruction and included gear in a focused half-day session
Hunt for Megalodon fossils on a Divemaster-led shore dive with gear provided
Hear prehistoric tales as you cruise at sunset in Venice, the Shark Tooth Capital
Soar up to 1,200 feet and enjoy panoramic views on an exhilarating parasail ride.
Explore Longboat Key’s mangrove islands at your own pace with fully equipped half-day rentals
Paddle crystal-clear bays to spot dolphins and manatees with expert naturalist guides
Explore scenic waters with included gear, map, and lesson for a fun half-day adventure
Paddle Sarasota's serene mangrove tunnels with a naturalist guide and spot birds, manatees, and dolphins.
Explore Lido Key’s mangrove tunnels with included gear, map, and a brief lesson
Fish inshore waters with a US Coast Guard–licensed captain on a 2019 Sea Pro, tailored for all ages
Enjoy a customizable 6–8 hour luxury sail on Sarasota Bay with captain and mate included
Enjoy a customizable luxury sail with captain and mate aboard a spacious 42-ft catamaran.
Experience a private dolphin tour and enjoy scenic views while learning about local wildlife.
Cruise the Intracoastal with room for up to 12 and flexible 4–8 hour rentals
Discover Jewfish Key and local sandbars on a private excursion with swimming and snorkeling opportunities.
Experience dolphins, sandbars, and a relaxing sunset cruise in the bays of Anna Maria Island.
See non-migratory dolphins and unique wildlife while exploring the bays of Manatee and Sarasota.
Stretch, unwind, and rejuvenate—right in the comfort of your vacation rental.
A custom chef‑curated feast celebrating bold local flavors and dietary wellness—served right in your home or rental
Siesta Key is a slice of coastal paradise on Florida’s Gulf Coast, famed for its powdery quartz sand, turquoise waters, and a laid-back beach town vibe that feels effortlessly elegant. Just off the coast of Sarasota, it’s a favorite for families, couples, and anyone who dreams of barefoot bliss and sunsets that linger long after the sun dips below the horizon.
Start your day with yoga on the beach or a paddle through mangrove tunnels. Grab a fresh juice or breakfast taco from a local caf before strolling through Siesta Village, where boutiques, ice cream shops, and beach bars welcome visitors with friendly charm. As the sun sets, join locals and travelers alike for the nightly drum circle on Siesta Beach -- a celebration of rhythm, community, and island joy.
Greetwell experiences in Siesta Key include private chef meals, in-home massage, family beach photography, or curated excursions like dolphin-watching tours or shelling adventures. Whether you're here for romance, rest, or reconnection, Siesta Key offers the rhythm of island life with just the right touch of luxury.