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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Keys Season Deals
Destination
Category
Marathon

Paradise Watersports Rentals

Explore the Florida Keys with top-quality boat and jet ski rentals for unforgettable adventures!

Key West

Florida Keys Boat Rental

Boat rentals from sleek SeaFox and pontoon models in Key West.

Islamorada

Three Waters Resort & Marina

Escape to Three Waters Resort & Marina for island luxury, ocean views, and endless adventure.Three Waters Resort & Marina, a Tribute Portfolio Resort, is a newly reimagined oceanfront destination in Islamorada, Florida, blending island charm with modern luxury.

Meetings Max
120
Total Space
1680 sq ft
Largest Room
1680 sq ft

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

Fisher Inn Resort and Marina

Fisher Inn Resort & Marina is an oceanfront boutique resort in Islamorada offering stylish rooms with kitchenettes, a heated pool with ocean views, and unique amenities like its own boat ramp and marina. Ideal for anglers, boaters, and families seeking waterfront comfort.

Key West

Happy Landings Marina

Key West marina with in-slip lifts & tight draft limit.

Key West

Key West Bight Marina

Historic Key West marina with deep water slips & walk-to everything charm.

Key Largo

The Pelican, Key Largo Waterfront Cottages

The Pelican Key Largo Cottages is a charming waterfront retreat located directly on Florida Bay in Key Largo, offering a serene and tropical escape just an hour from Miami International Airport.

Key Largo

Upper Keys Sailing Club

Upper Keys Sailing Club — community sailing club and regatta venue on Buttonwood Sound in Key Largo, Florida.

Key West

The Water Traveler Vacations

The Water Traveler is your luxury guide to private boat charters, all-inclusive captained getaways, and bespoke waterfront events.

Key West

Bayfront Suites Resort & Marina

Bayfront Suites in Key West offers luxury waterfront condos with modern amenities, a rooftop veranda, and a private marina. Perfect for both relaxation and special events.

Key Largo

Blue Fin Rock Harbor RV Park & Marina

RV Key Largo (Blue Fin Rock Harbor Marina & RV Resort) offers oceanfront and oceanview RV sites with full hookups, cable, and water access—ideal for families, anglers, and road-trippers exploring the Florida Keys.

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.

The Lower Keys

Sugarloaf Key Hotel at KOA Resort

Tropical seaside stay with marina access and on-site dining.