Kayaking in Gulf Gate Estates

One- or Two-Hour Kayak or Paddleboard Rentals for One or Two at Watersports at Little Harbor Resort (Up to 60% Off)

Water Sports at Little Harbor

Little Harbor Resort

$25 $12

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One- and two-seater kayaks; easy-to-navigate paddleboards; region teeming with dolphins, stingrays, and manatees

Paddleboard or Kayak Rental or SUP Yoga from Lotto Boat (Up to 67% Off). Four Options Available.

Lotto Boat

St. Petersburg

$32 $14

Spend an afternoon piloting a standup paddleboard, kayak, or double kayak, or take in some aquatic yoga atop a paddleboard

Half-Day Kayak Rental for One or Two or Two-Hour Paddleboard Rental at Cove Cay Marina (Up to 50% Off)

Cove Cay Marina

Largo

$30 $15

Climb aboard a paddleboard, or a one-person or tandem kayak and drift past mangrove trees, red fish, and manatees

One-Hour or Half-Day Paddleboard or Kayak Rentals for Two or Four at Sand Key Paddle Sports (Up to 57% Off)

Sand Key Paddle Sports

Sand Key

$60 $29

Explore the crystal-clear waters of Clearwater Harbor atop a paddleboard or kayak during one-hour or half-day rentals

Guided Kayak Tours and Rentals from Nature Tours and More (Up to 59% Off). Five Options Available.

Nature Tours and More

Multiple Locations

$80 $40

Guided tours and rented kayaks explore local habitats, spotting everything from manatees and dolphins to gators and bats

$44 for $80 Worth of Kayak Rental — First Mate and Bait

First Mate And Bait

Hancock

$80 $44

Local businesses like this one promote thriving, distinctive communities by offering a rich array of goods and services to locals like you

Four-Hour Kayak Excursion for One, Two, or Four from FMB FlyBoard (Up to 57% Off)

FMB FlyBoard

Getaway Marina

$40 $19

Kayakers explore the natural wonders of Fort Myers Beach, paddling past pristine beaches, lush vegetation and beautiful coastal wildlife

Kayak or Standup-Paddleboard Rental from Nature Recreation Management of Lee County, LLC-Lover's Key (Up to 57% Off)

Nature Recreation Management of Lee County, LLC-Lover's Key

Fort Myers Beach

$38 $19

Get up-close & personal with wildlife kayaking around Lover's Key in a 1- or 2-person vessel; test your balance on a standup paddleboard

One or Two Half-Day Kayak Rentals at Belle Harbour Marina (Up to 56% Off)

Belle Harbour Marina

Tarpon Springs

$40 $20

Kayaker gets four hours to explore Anclote River

Half- or Full-Day Rental of a Single or Tandem Kayak from Windsong Charters (Up to 57% Off)

Windsong Charters

New Port Richey

$45 $21

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Captains outfit clients for paddle amid the wildlife, hidden channels, and sunken boats of Florida's coastline

2.5-Hour Kayak Tour for Two, Four, or Six People from Kayakmarco.com (Up to 52% Off)

Kayakmarco.com

Isle of Capri Kayak Park

$138 $67

During guide-led tours, both beginner and experienced kayakers enjoy the local natural area and wildlife while paddling around Marco Island

Select Local Merchants

Mark Toomey once helmed his own recruitment firm in Nottingham, England, on the outskirts of Sherwood Forest, but a disdain for damp winters led him to the sun-drenched beaches of Siesta Key. Since opening Robin Hood Rentals in 2009, Mark has persevered through what he calls "Florida's harshest winter in 30 years," during which temperatures teetered near the freezing mark. He equips visitors with rental land-based and aquatic craft that let them explore the area without having to saddle a horse or propose to a dolphin.

From its perch near the Jim Neville Marine Preserve, the company fits cyclists with a range of beach, mountain, and tandem bicycles; matches riders to a fleet of two-seat 49cc automatic scooters; and trains visitors to venture off on newer-model i2 LeanSteer Segways. They also let kayakers explore the local waterways from sunrise into the nighttime.

5129 Ocean Blvd
Siesta Key,
FL
US

The spindly branches of mangrove trees dip into Sarasota waters, often creating channels just wide enough to admit one kayak. But despite the narrow nature of these waterways, the guides of I Kayak Sarasota—all Sarasota natives—navigate them with ease. They do this while leading kayakers on tours that uncover different aspects of the bay’s natural splendor without revealing its real secret—that it’s actually a giant’s bathtub. One tour showcases the mangrove tunnels where tourists might see manatees and dolphins, and the other grants guests views of the sunset from the middle of the bay. In addition, I Kayak Sarasota offers standup-paddleboard lessons, which incorporate balance and core fitness into wave-top adventures.

200 John Ringling Boulevard
Sarasota,
FL
US

Sarasota Wind and Water Adventures gives adventurers the vessels and knowledge to plunge boldly into the surf, providing paddleboard, kayak, and waterski rentals as well as lessons. Fishing trips set sail for open water with a Coast Guard-certified captain and all of the tackle necessary to hunt for kingfish, triggerfish, and the vengeful ghosts of scuba divers, while sunset cruises let passengers experience the wonder of voyaging directly into the heart of the sun.

1518 Stickney Point Rd
Sarasota,
FL
US

With backgrounds in marine science and conservation, Sea Life Kayak Adventures’ guides tailor their tours to highlight the Sarasota coastline's natural splendor. They limit their expeditions to no more than 10 kayakers at a time, allowing groups to glide quietly through bays and mangrove islands without disturbing nesting herons, ambling manatees, or staring contests between sea cucumbers. Additionally, their vast knowledge of the region’s best bird-watching islands and sea-life feeding grounds empowers guides to customize tours to suit each group’s wildlife-watching ambitions. Dedicated to giving back to the waters that support their passions and livelihoods, Sea Life Kayak Adventures' owners and guides are members and volunteers at organizations including the Wildlife Education & Rehabilitation Center Inc., Sarasota Bay Estuary Program, and the Save the Manatees Foundation.

8918 Midnight Pass Road
Sarasota,
FL
US

Kayak Boca Grande's knowledgeable guides unveil Florida's natural marine beauty and untamed wildlife during kayak tours through the Mangrove Tunnels and the beautiful calm waters of Gasparilla Bay. As paddlers propel themselves over the sparkling water, they find themselves sharing the splendor of the Gulf Coast with fauna such as dolphins, manatees, and great blue herons. Those who may have already taken a guided trip or prefer to chart their own course can rent a kayak instead and go out for a self-guided spin.

8900 Midnight Pass Rd
Sarasota,
FL
US

Since he was six, Nate Dunn has explored almost every form of water-bound sport, including surfing, kayaking, sailing, and even commercial fishing. Now his experiences allow Nate to share his knowledge of the water with locals, doling out rental paddleboards and kayaks. During his guided eco-tours, bobbing wanderers get views of mangroves, local wildlife, and disappointed surfers from the placid waters.

5511 Calle Del Invierno
Sarasota,
FL
US