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Best 576

things to do in Osprey, FL

Showing 481-504 of 576 results
SUP Yoga Class on Holmes Beach Waters

SUP Yoga Class on Holmes Beach Waters

Practice yoga on a paddleboard and connect with nature in a tranquil setting.

5.0 • 625 reviews
$75/ person
Paddle Pristine Mangrove Tunnels in Neal Preserve

Paddle Pristine Mangrove Tunnels in Neal Preserve

Explore mangrove tunnels by kayak or paddleboard with experienced guides in Neal Preserve.

5.0 • 625 reviews
$55/ tour
2-3 Hour Guided Jet Ski Tour of Anna Maria Island

2-3 Hour Guided Jet Ski Tour of Anna Maria Island

Guided island cruising with photo stops and group-paced riding

5.0 • 243 reviews
$429& up
24' Pontoon Boat Rental in Palmetto with Sandbar Access
Up to 13

24' Pontoon Boat Rental in Palmetto with Sandbar Access

Cruise with up to 13 friends on a spacious pontoon equipped for sandbar hopping

5.0 • 168 reviews
$599& up
Captained Tritoon Cruise in Anna Maria Island

Captained Tritoon Cruise in Anna Maria Island

Cruise Anna Maria Island by captained tritoon with room for up to 6

5.0 • 168 reviews
$396& up
Siesta Key Private Catamaran Charter
Up to 49

Siesta Key Private Catamaran Charter

Customize your day exploring sandbars, islands, and marine life on a private catamaran.

4.9 • 9.2K reviews
$1,248& up
Kayak & Paddleboard Rental at Turtle Beach

Kayak & Paddleboard Rental at Turtle Beach

Rent a kayak or paddleboard and explore Turtle Beach waterways with a provided map

4.9 • 3.2K reviews
$51/ kayak
21' Tritoon Boat Rental in Sarasota
Up to 10

21' Tritoon Boat Rental in Sarasota

Cruise Sarasota’s intracoastal waterways on a 21' Bennington tritoon for up to 10

5.0 • 78 reviews
$480/ boat
2.5-Hour Sandbar Cruise in Holmes Beach

2.5-Hour Sandbar Cruise in Holmes Beach

Cruise to a local sandbar and swim or snorkel

4.9 • 1.8K reviews
$78/ person
2-Hour Dolphin & Wildlife Cruise in Holmes Beach

2-Hour Dolphin & Wildlife Cruise in Holmes Beach

Cruise the Gulf and back bay to look for dolphins and seasonal manatees

4.9 • 1.8K reviews
$62/ person
Anna Maria Island 2-Hour Sunset Cruise

Anna Maria Island 2-Hour Sunset Cruise

Cruise into the evening and watch the sunset from the water

4.9 • 1.8K reviews
$66/ person
24' Pontoon Boat Rental in Holmes Beach
Up to 10

24' Pontoon Boat Rental in Holmes Beach

Set your own course for sandbars, swims, and open-water exploring

4.9 • 1.8K reviews
$588/ boat
Private Tiki Boat Cruise in Holmes Beach

Private Tiki Boat Cruise in Holmes Beach

Slide and explore sandbars aboard a private two-story tiki boat

4.9 • 1.8K reviews
$766& up
2-Hour Dolphin Tour in Holmes Beach

2-Hour Dolphin Tour in Holmes Beach

Private time on the water to look for dolphins and seasonal wildlife

4.9 • 1.8K reviews
$472
Private Island Snorkeling Charter in Holmes Beach

Private Island Snorkeling Charter in Holmes Beach

Island hopping, snorkeling and shelling for your private group

4.9 • 1.8K reviews
$684& up
Bachelorette Boat Charter Anna Maria Island

Bachelorette Boat Charter Anna Maria Island

Private island boat party for your bachelorette celebration

4.9 • 1.8K reviews
$766
Sunset Cruise to Egmont Key

Sunset Cruise to Egmont Key

Explore Egmont Key, then watch the sky change on a private evening cruise

4.9 • 1.8K reviews
$567
Anna Maria Island Sunset Cruise

Anna Maria Island Sunset Cruise

Watch the sunset from the water aboard the Salty Dolphin

4.9 • 1.8K reviews
$508
Sea Ray SDX 250 Boat Rental in Sarasota
Up to 12

Sea Ray SDX 250 Boat Rental in Sarasota

Rent a Sea Ray SDX 250 for 6 hours with seating for up to 12

4.9 • 950 reviews
$1,002
Jet Ski Rental in Sarasota

Jet Ski Rental in Sarasota

Ride a jet ski on Sarasota's waters

4.9 • 950 reviews
$202/ jet ski
Englewood 3-Hour Single Kayak Rental

Englewood 3-Hour Single Kayak Rental

Paddle Lemon Bay independently in a stable sit-on-top kayak

4.9 • 892 reviews
$45/ kayak
Sarasota Happy Hour Dolphin Cruise

Sarasota Happy Hour Dolphin Cruise

Relax on a Sarasota Bay happy hour cruise and watch for dolphins

5.0 • 71 reviews
$88/ person
Sarasota Sunset Charter

Sarasota Sunset Charter

Private Yellowfin cruise with sandbar swimming and sunset views

4.9 • 517 reviews
$1,547
Offshore Fishing Charter on Kai Fin

Offshore Fishing Charter on Kai Fin

Fish offshore with a USCG-licensed captain, mate, bait, and standard fuel included

4.9 • 517 reviews
$5,102
1…202122…24
Boat Tours83Boat Rentals71Yacht Charters62Kayaking Tours58Fishing Charters37
More
  • 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