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Best 576

things to do in Osprey, FL

Showing 313-336 of 576 results
Fishing-Ready Pontoon Boat Rental in Bradenton
Up to 12

Fishing-Ready Pontoon Boat Rental in Bradenton

Cruise with Bluetooth audio, a swim ladder, and fishing-ready features

5.0 • 19 reviews
$280/ boat
Bradenton 8-Person Fishing Boat Rental
Up to 8

Bradenton 8-Person Fishing Boat Rental

Take the helm of a fishing-ready center console with navigation and 10 rod holders

5.0 • 19 reviews
$280/ boat
Guided Beach & Pier Fishing Trip in Sarasota

Guided Beach & Pier Fishing Trip in Sarasota

Learn shoreline fishing techniques with a captain along Sarasota's Gulf Coast

4.9 • 30 reviews
$318& up
Guided Beach Snook Fishing Trip in Sarasota

Guided Beach Snook Fishing Trip in Sarasota

Target snook from Sarasota's shoreline with a guide

4.9 • 30 reviews
$424
16' Pontoon Boat Charter in Venice, FL
Up to 6

16' Pontoon Boat Charter in Venice, FL

Cruise open water for sightseeing, swimming, parties, and sunset views

4.9 • 23 reviews
$319& up
Sunset Cruise Anna Maria Island

Sunset Cruise Anna Maria Island

Tailored private cruises for sunsets, wildlife, and celebrations

5.0 • 15 reviews
$530
Private Fishing Charter in Holmes Beach

Private Fishing Charter in Holmes Beach

Fish Anna Maria waters with a fourth-generation local captain

5.0 • 15 reviews
$1,060& up
3-Hour Guided Fishing Charter in Bradenton Beach

3-Hour Guided Fishing Charter in Bradenton Beach

Cast the backcountry flats with gear, bait, and your fishing license included

5.0 • 13 reviews
$429
Bradenton Beach 4-Person Fishing Charter

Bradenton Beach 4-Person Fishing Charter

Cast, troll, or jig with bait, tackle, and a fishing license included

5.0 • 13 reviews
$1,145
4-Hour Fishing Charter in Bradenton Beach

4-Hour Fishing Charter in Bradenton Beach

Fish local waters with provided gear, bait, and a captain

5.0 • 13 reviews
$572
Catch & Release Fishing Charter in Bradenton Beach

Catch & Release Fishing Charter in Bradenton Beach

Cast a line on a relaxed, captain-led trip with gear and fishing license included

5.0 • 13 reviews
$286
Guided Snorkeling Charter at Egmont Key

Guided Snorkeling Charter at Egmont Key

Cruise to historic fort ruins for snorkeling and island exploration

5.0 • 13 reviews
$565& up
Sunset Cruise in Bradenton Beach

Sunset Cruise in Bradenton Beach

A private captain-led outing for sandbars, snorkeling, and sunset views

5.0 • 13 reviews
$266& up
Grand Sarasota VIP Helicopter Tour

Grand Sarasota VIP Helicopter Tour

See Sarasota’s coastline and Sunshine Skyway Bridge on a 50-minute helicopter flight

4.7 • 277 reviews
$381
Downtown Sarasota Helicopter Tour Over St. Armands Circle

Downtown Sarasota Helicopter Tour Over St. Armands Circle

See Downtown Sarasota landmarks from the air on a 20-minute helicopter flight

4.7 • 277 reviews
$190
Fly a Private Romantic Helicopter Tour in Sarasota

Fly a Private Romantic Helicopter Tour in Sarasota

Private Sarasota helicopter ride with champagne, roses, and music

4.7 • 277 reviews
$222
Sarasota Beach & Wildlife Helicopter Tour

Sarasota Beach & Wildlife Helicopter Tour

30-minute helicopter flight over Sarasota beaches and coastal landmarks

4.7 • 277 reviews
$264
Sarasota Sunset Helicopter Tour Over St. Armands Circle

Sarasota Sunset Helicopter Tour Over St. Armands Circle

See Sarasota glow at sunset on a 20-minute helicopter flight

4.7 • 277 reviews
$211
Englewood 90HP Pontoon Rental
Up to 11

Englewood 90HP Pontoon Rental

Cruise, fish, shell, or picnic aboard a 90HP pontoon

4.8 • 33 reviews
$367/ boat
Englewood 90HP Pontoon Boat Rental
Up to 9

Englewood 90HP Pontoon Boat Rental

Cruise Lemon Bay and stop at Stump Pass on a family-friendly pontoon

4.8 • 33 reviews
$367/ boat
Lemon Bay Skiff Rental
Up to 6

Lemon Bay Skiff Rental

Fish and cruise Lemon Bay’s backwaters aboard a 50HP skiff

4.8 • 33 reviews
$241/ boat
Englewood 21' Fishing Boat Rental
Up to 6

Englewood 21' Fishing Boat Rental

A fishing-ready center console for bridges and beaches around Manasota Key

4.8 • 33 reviews
$385/ boat
Manasota Key Bayliner Deck Boat Rental
Up to 8

Manasota Key Bayliner Deck Boat Rental

Cruise Manasota Key with shade, storage and Bluetooth sound

4.8 • 33 reviews
$367/ boat
Full-Day Aventon E-Bike Rental in Sarasota

Full-Day Aventon E-Bike Rental in Sarasota

Explore Sarasota at your own pace on a fully equipped Aventon Pace 500.3 e-bike

4.8 • 31 reviews
$79/ bike
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Boat Tours83Boat Rentals71Yacht Charters62Kayaking Tours58Fishing Charters37
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  • Jet Skiing33
  • Dolphin Watching27
  • Bike Rentals21
  • Sunrise and Sunset Tours17
  • Snorkeling14
  • Car Rentals12
  • Train Tours12
  • Horseback Riding9
  • Parasailing9
  • Equipment Rental8
  • Food Tours8
  • Ferries7
  • Helicopter Tours7
  • Outdoor Picnics7
  • Paddleboarding7
  • Stand Up Paddle Boarding6
  • Trolley Tours6
  • Sailing5
  • Scooter Rentals5
  • Private Boat Charters4