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.

Filters
Keys Season Deals
Destination
Category
Islamorada

Tavernier Creek Marina

Tavernier Creek Marina — full-service Keys marina with dry storage, wet slips, and ocean access.

Islamorada

Seahorse Water Adventures

Explore reef, sandbars, and waves with jet skis, boats, and snorkeling adventures by Seahorse Water Adventures.

Key Largo

The Buzzard's Roost

Tucked at the end of North End Road at Garden Cove, mile marker 106.5 oceanside, which means you can drive in or tie up and walk off the dock. Sunday brunch comes with steel drums and the first mimosa on the house.

Islamorada

Caloosa Cove Resort

Fifteen acres on the ocean at mile marker 73.5, with 30 suites that all have kitchens, balconies and water out the front door, plus a heated pool and a sandy beach. Tie your boat up out back, walk over to Habano's for Cuban food, and never move the car.

Key Largo

Gilbert's Resort & Marina

Gilbert’s Resort & Marina is a laid-back waterfront resort in Key Largo, featuring waterfront rooms, a private beach, and the Keys’ largest tiki bar with live music and dining.

Weddings Max
1000

Islamorada

The Caribbean Resort

The Caribbean Resort in Islamorada offers 22 private, Caribbean-style homes with ocean views, a beach-entry pool, fishing pier, and complimentary use of bicycles, kayaks, and paddleboards.

Key Largo

Calypso Sailing

Calypso Watersports offers private sailing charters aboard Leopard Catamarans in Key Largo and Key West, providing unforgettable journeys tailored to suit every need.

Marathon

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Waterfront resort in Marathon offering coastal luxury, a full-service marina, spa, dining, four pools, and a sister property, Courtyard by Marriott.

Weddings Max
130
Meetings Max
130
Total Space
1820 sq ft
Largest Room
1820 sq ft

Islamorada

Florida Keys Dive Center

Three-dive adventures, snorkeling & scuba charters from Islamorada with courses & lobstering.

Islamorada

Z Flight Watersports | Islamorada FL

Soar with Z-Flight Watersports—book your unforgettable adventure today.

Key West

Key West Community Sailing Center

Learn to sail and enjoy vibrant community events at Key West Sailing Center!

Key Largo

Tarpon Flats Inn & Marina

Tarpon Flats Inn & Marina is a boutique waterfront retreat in Key Largo, offering five spacious, air-conditioned rooms with kitchenettes, private beach access, and complimentary kayaks for exploring the surrounding waters.

Key West

Argo Navis Key West Sailing Charters

Argo Navis is a 75-foot luxury catamaran offering intimate, all-inclusive sailing experiences in Key West, including sunset cruises, brunch sails, and private charters, with curated food and drink pairings.

Key West

Key West Historic Seaport

Key West Historic Seaport is a vibrant waterfront hub with world-class dining, unique shops, water excursions, live music & year-round events in a 20-acre scenic harbor location.