Boat speeding on water with people cheering, under a clear blue sky.

Boating & On The Water

In The Florida Keys, life flows with the tide. Rent a skiff for backcountry exploring, hop on a sunset cruise, or join locals at a sandbar party where the water is the dance floor. Paddleboards and kayaks slip quietly through mangroves, while sailboats and charters head offshore for bigger adventures. With marinas, rentals, and tours across the islands, getting on the water is easy—and unforgettable. Sunshine, salt air, and stories worth retelling are all included.

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Key Largo

Key Largo Princess Glass Bottom Boat

Glass-bottom cruises over Molasses Reef—see the reef without getting wet.

Islamorada

Florida Keys Watersports

Boat & jet ski rentals + tours exploring reefs, mangroves & sandbars in Islamorada.

Key Largo

Key Largo Parasail

USCG-certified parasail adventures: soar over Key Largo’s waters in style.

Key West

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West is a historic oceanfront resort featuring elegant accommodations, beachfront amenities, and classic island charm.

Weddings Max
300
Meetings Max
550
Total Space
11000 sq ft
Largest Room
5000 sq ft

Marathon

Coconut Cay Resort & Marina

Escape to Coconut Cay Resort in Marathon, FL—serene waterfront stays with free bikes, kayaks, and nearby beaches.

Marathon

Caribbean Soul Charters

Waterfront Florida Keys rental with sailboat included—perfect for sailors and nature lovers!

Key Largo

American Sailing Academy

Learn to sail in paradise: ASA-certified courses in Key Largo.

Key Largo

Florida Bay Club

Florida Bay Club is a laid-back, Key Largo timeshare resort offering spacious 2- and 3-bedroom units with full kitchens and balconies, plus a heated pool, docks, and bayfront access—perfect for families and boating enthusiasts.

The Lower Keys

Sugar Loaf Lodge

Sugarloaf Lodge is a waterfront retreat located at Mile Marker 17 on the Overseas Highway, offering 31 rooms with private patios or balconies overlooking the serene Lower Sugarloaf Sound.

Key Largo

The Mark Sorensen Youth Sailing Program

Mark Sorensen Youth Sailing — nonprofit sailing school in the Keys teaching kids boat handling, safety & seamanship.

Marathon

Sun Outdoors Marathon

Sun Outdoors Marathon: waterfront RV resort with marina and Gulf views.

Key West

Boca Chica Marina

Boca Chica Marina on the West side of Boca Chica Key offers boat slips, moorings, and a full range of amenities including dining, beach access, and watersport rentals.

Marathon

Z Flight Watersports | Marathon FL

Zip into the sky with Z-Flight Watersports: parasailing thrills await.