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Best results for

Kayaking Tours in Osprey, FL

Showing 25-48 of 58 results
Sunset to Night Glow Kayak Tour in Bradenton

Sunset to Night Glow Kayak Tour in Bradenton

See Florida sunset colors from a clear tandem kayak

5.0 • 43 reviews
$79/ person
Sunset Kayak Tour in Osprey

Sunset Kayak Tour in Osprey

Paddle mangroves after sunset with LED-lit views beneath your kayak

5.0 • 8 reviews
$69/ person
Double Kayak Rental in Anna Maria Island

Double Kayak Rental in Anna Maria Island

Paddle together with free local beach delivery and pickup

4.6 • 275 reviews
$62/ kayak
Private Mangrove Tunnel Kayak & Paddleboard Tour in Sarasota

Private Mangrove Tunnel Kayak & Paddleboard Tour in Sarasota

Paddle Lido Key mangrove tunnels with a private guide

4.9 • 3.2K reviews
$91/ kayak
4-Hour Lido Key Kayak Rental in Sarasota

4-Hour Lido Key Kayak Rental in Sarasota

Paddle the Lido Key Mangrove Tunnels with a 4-hour single or tandem kayak rental

5.0 • 3.7K reviews
$51/ kayak
Single Kayak Rental in Osprey

Single Kayak Rental in Osprey

Paddle southwest Florida waterways at your own pace

4.6 • 117 reviews
$32/ kayak
Explore Lido Key Mangrove Tunnels Kayak Rental

Explore Lido Key Mangrove Tunnels Kayak Rental

Rent a single or tandem kayak and paddle the Lido Key mangrove tunnels

5.0 • 3.7K reviews
$51/ kayak
Siesta Key Mangrove Kayak Tour

Siesta Key Mangrove Kayak Tour

Paddle mangrove tunnels and visit Midnight Pass Beach with a local guide

5.0 • 196 reviews
$70& up
Private Naturalist-Led Kayak Tour in Longboat Key

Private Naturalist-Led Kayak Tour in Longboat Key

Paddle the waters between Anna Maria Island and Longboat Key with your own private guide

5.0 • 658 reviews
$735
Nokomis Self-Guided Single Kayak Rental

Nokomis Self-Guided Single Kayak Rental

Paddle Gulf Coast waters at your own pace and explore nearby islands

5.0 • 196 reviews
$47/ kayak
Private Kayak or Paddleboard Tour in Siesta Key

Private Kayak or Paddleboard Tour in Siesta Key

Paddle Midnight Pass on a private Siesta Key kayak or paddleboard tour

4.9 • 3.2K reviews
$91/ person
Neal Preserve 2-Hour Pedal Kayak Tour

Neal Preserve 2-Hour Pedal Kayak Tour

Pedal through seagrass beds and mangrove tunnels on a 2-mile Neal Preserve tour

4.9 • 196 reviews
$78/ kayak
Guided Kayak Tour of Emerson Point Mangroves

Guided Kayak Tour of Emerson Point Mangroves

Paddle mangrove tunnels and explore sandbars in Terra Ceia Bay

4.9 • 169 reviews
$55/ kayak
Anna Maria Island Sound Glow Kayak Tour

Anna Maria Island Sound Glow Kayak Tour

Paddle a clear, LED-lit kayak through Anna Maria Island Sound after dark

5.0 • 43 reviews
$79/ person
3-Hour Clear Kayak Rental in Osprey

3-Hour Clear Kayak Rental in Osprey

Explore the water at your own pace in a clear kayak

5.0 • 8 reviews
$53/ person
Single Kayak Rental on Anna Maria Island

Single Kayak Rental on Anna Maria Island

Flexible rental periods with free local beach delivery and pickup

4.6 • 275 reviews
$40/ kayak
Anna Maria Island Sunset Kayak Tour

Anna Maria Island Sunset Kayak Tour

Toast the sunset on a guided Gulf Coast kayak paddle

5.0 • 658 reviews
$85/ kayak
3-Hour Kayak Rental at Emerson Point

3-Hour Kayak Rental at Emerson Point

Choose a single or tandem kayak with free delivery to your location

4.9 • 169 reviews
$48/ kayak
Osprey Tandem Kayak Rental

Osprey Tandem Kayak Rental

Explore southwest Florida waterways by kayak with included paddles and life jackets

4.6 • 117 reviews
$46/ kayak
Guided Eco Kayak Tour in Nokomis

Guided Eco Kayak Tour in Nokomis

Paddle Gulf Coast waters and discover barrier islands with a guide

5.0 • 196 reviews
$70& up
Private Sunset Kayak Tour on Anna Maria Island

Private Sunset Kayak Tour on Anna Maria Island

Paddle with a dedicated guide as the Florida Gulf Coast sun sets

5.0 • 658 reviews
$735
Nokomis Double Kayak Rental

Nokomis Double Kayak Rental

Paddle Gulf Coast waters and explore nearby islands at your own pace

5.0 • 196 reviews
$59/ kayak
LED Night Clear-Bottom Kayak Tour in Sarasota

LED Night Clear-Bottom Kayak Tour in Sarasota

Feed fish and spot marine life beneath LED-lit clear-bottom kayaks

$70/ person
Private Mangrove Tunnels Kayak Tour on Lido Key

Private Mangrove Tunnels Kayak Tour on Lido Key

Paddle Lido Key’s mangrove tunnels with a private guide from Ted Sperling Nature Park

5.0 • 658 reviews
$735
123
Osprey Things To Do
Kayaking ToursBoat Tours82Boat Rentals70Yacht Charters62Fishing Charters37
More
  • Jet Skiing29
  • Dolphin Watching27
  • Bike Rentals21
  • Sunrise and Sunset Tours17
  • Snorkeling14
  • Car Rentals12
  • Train Tours12
Horseback Riding
9
  • Parasailing9
  • Equipment Rental8
  • Food Tours8
  • Helicopter Tours7
  • Outdoor Picnics7
  • Paddleboarding7
  • Stand Up Paddle Boarding6
  • Trolley Tours6
  • Sailing5
  • Scooter Rentals5
  • Private Boat Charters4
  • Scuba Diving4