Kayaking in Keystone


Four-Hour or Eight-Hour Rental of a Single or Tandem Kayak from Windsong Charters (Up to 57% Off)

Windsong Charters

Windsong Charters

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

$45 $21

View Deal

Two- or Four-Hour Kayak Rental for Two People at Kayak Valet (Up to 51% Off)

Kayak Valet

Multiple Locations

Kayaks designed for safety and stability engage first-timers in water sports.

$80 $39

View Deal

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

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

$30 $15

View Deal

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 Park

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

$60 $29

View Deal

Kayak, or Paddleboard Day Trip for 1, 2, or 4, or Overnight Canoe Trip for 2, 4, or 8 (Up to 53% Off)

Santa Fe Canoe Outpost

High Springs

Paddle or swim along the banks of the Santa Fe River, where you can spy some of Florida’s famous springs

$40 $20

View Deal

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

Lotto Boat

St. Petersburg

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

$32 $14

View Deal

Paddleboard, Kayak, or Bike Rental for Two from Shoreline Surf & Skate Shop (50% Off)

Shoreline Surf & Skate Shop

Shoreline Surf & Skate Shop

Customers enjoy the great outdoors by land or by sea with paddleboard, kayak, and bike rentals

$40 $20

View Deal

One- or Two-Hour Kayak or Paddleboard Rentals for One or Two at Watersports at Little Harbor (Up to 56% Off)

Watersports at Little Harbor

Little Harbor Resort

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

$25 $13

View Deal

Select Local Merchants

  • Wheel Fun Rentals CORPORATE
    When Brian McInerney reflects on the humble beginnings of Wheel Fun Rentals, he points to his childhood passion for bikes. "As far back as I can remember, I had a real love affair with bicycles," he recalls. During a trip to Italy in 1987, Brian's affinity for cycling blossomed into a full-fledged obsession when he spotted locals' transporter of choice, the surrey. Inspired, he began importing the Italian four-wheelers to a rental business in the U.S. that eventually expanded into Wheel Fun Rentals, now a nationwide web of shops that also loans out bikes, electric cars and mopeds, and man-powered watercraft. Adventuresome athletes can also compete in activities such as surrey scavenger hunts and blindfold obstacle courses navigated via shouted instructions from a seeing teammate or exceptionally long rounds of trial and error.
    Read More
    1700 Sunset Drive
    Tarpon Springs, FL US
  • Pinellas County Park Department
    Whether by deck, pontoon, or center console boat, Belle Harbour Boat Rentals gets people enjoying the water without the hassle of watercraft ownership. From the Belle Harbour Marina, travelers make their way along the Anclote River and inter-coastal waterways in search of sights, sun, and fish. Along the way, they find miniature islands and sandbars, perfect for picnics or building sand sculptures of feet for taunting merpeople. Fishing excursions yield bounties of seatrout, redfish, and snook or a chance to view early-morning glimpses of Anclote Key Lighthouse. Along the way, waterside eateries beckon groups for a quick bite with their burgers, seafood, and drinks before customers journey back out to share dining critiques with the manatees, dolphins, bald eagles, and osprey that inhabit the area.
    Read More
    307 Anclote Rd
    Tarpon Springs, FL US
  • New Port Richey
    "We've got more canoes, kayaks and SUPs than fingers and toes to count them," Captain Wendy explains. "Also, two sailboats, eleven pontoons??all rentable. The funny thing is, this business came from a big accident." She's referring to the company?s inception in 2002, when a devastating hurricane led a friend to sign his company?s single sailboat over to Wendy and her husband, Bruce. "We were in marketing??then, suddenly, we were in boating." More than 12 years later, Windsong Charters & Boat Rentals has flourished under the duo?s stewardship. The company now performs 200 weddings each year and equips a wide range of patrons to revel in the breathless joy of cutting through playful zephyrs and out across the water. Wendy and Bruce encourage fishing and bringing pets on boating voyages, and the two share stories to delight guests or calm champagne bottles propped next to brand-new yachts. As propellers hum to life and paddles make a gentle kissing sound against the surf, visitors scan the horizon for the variety of wildlife that slips along just below the surf's surface or comes wheeling out of tufts of cumulonimbus. "I wish the animals would give us their schedules,? Wendy says, ?but, on a given day, you could see manatees, dolphins, stingrays, and lots of birds."
    Read More
    4927 US Highway 19
    New Port Richey, FL US
  • Pasco Paddlepalozza
    For one weekend every April, Port Richey transforms into Pasco Paddlepalooza, a man-powered boat festival comprising three races. The festival's crown jewel is the Durney Key Challenge: a 2.3-mile race that challenges paddlers to slalom around turn-of-the-century stilt houses that stud the open water. The Salt Springs Alliance Classic and Battle in the Bayou focus on more straightforward feats: open-water kayaking and dragon boating, respectively. Though it sounds like a race between two beautiful dragons in boats, dragon boating is executed by humans rowing traditional Chinese boats, traveling in two side-by-side columns. But there's plenty to do on land, too. The festival also encompasses a craft beer festival, and abuts well-maintained campgrounds, where visitors commune comfortably with the outdoors, much like homeowners who leave their windows open for the neighborhood squirrels.
    Read More
    5419 Treadway Drive
    Port Richey, FL US
  • Lotto Boat
    Boats dance and glide over the crisscrossing wakes carved into Tampa Bay, each craft anxiously revving toward its respective dock to arrive before closing time. All the while, a handful of boats remain on the open water, swaying atop the undulating waves as its passengers continue to enjoy the fiery sunset reflecting off the bay's surface. These select aquatic vehicles carry Lotto Boat's boat club members, who have access to a slew of exclusive perks, such as extended marina hours. Stationed at Harborage Marina, Lotto Boat's 45 rental vessels include kayaks, paddleboards, WaveRunners, and power boats equipped with GPS navigation systems. After hopping aboard a vessel, landlubbers can go jet-skiing, drift over to nearby tiki bars for dinner and live music, or take in scenic views of downtown St. Petersburg. Once patrons make their way back to one of Lotto Boat's two docks, staffers thoroughly cleanse the boat of interior debris and exterior mermaid hitchhikers to prepare for the vessel's next excursion.
    Read More
    970 Franklin Court
    Palm Harbor, Florida US
  • Palm Harbor Parks & Recreation
    CSA Palm Harbor keeps its neighborhood moving. As the managing body of parks, recreation, and leisure services for the unincorporated community of Palm Harbor, the outfit takes charge by providing affordable, high-quality facilities and programs. CSA Palm Harbor manages three multi-sport complexes and a full-service community activity center. Outside those doors, though, their efforts ripple through the community. They include a municipal kayak launch, a waterside park, fitness workshops, 5K fun runs, and camps for kids who don't want to spend their summer memorizing yearbook messages.
    Read More
    1550 16th Street
    Palm Harbor, FL US
Advertisement