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
Marathon

Seascape Resort and Marina

Seascape Resort & Marina: serene oceanfront escape with pool, marina, and tropical charm.Seascape Resort & Marina is a tranquil oceanfront retreat in Marathon featuring a private beach, marina access, an outdoor pool, and complimentary kayaks, paddleboards, bicycles, and grilling facilities.

Marathon

Z Flight Watersports | Marathon FL

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

Key West

Salty Bottom Boats

Salty Bottom Boat — private custom charters in Key West for sandbar parties, sunset cruises & island adventures.

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

Key West

Key West Express

Key West Express — high‑speed ferry service from Fort Myers Beach and Marco Island to Key West for relaxing day trips or island adventures.

Islamorada

A1A Watersports and Boat Rentals

A1A Watersports & Boat Rentals is a family-owned operation at Mile Marker 85.9 in Islamorada offering year-round jet ski tours, WaveRunner freedom rides, and self-guided boat rentals with a large fleet and guided island adventures.

Islamorada

Robbie's of Islamorada

Robbie’s of Islamorada offers thrilling tarpon feeding, fishing, water sports, and vibrant local dining in the heart of the Florida Keys.

Key West

Namaste' Eco Excursions

Namaste’ ECO-Excursions delivers immersive, eco-focused reef and mangrove snorkeling adventures in Key West—small-group, “citizen science” tours with expert guides, coral assessments, and hands-on ecology presentations.

Key West

Adventures Key West

Adventures Key West is a full-service Key West experience booking company curated by local experts, offering everything from on-water adventures and private charters to golf cart and scooter rentals, cultural workshops, wellness experiences, and private event and wedding bookings throughout Key West.

Weddings Max
200

Islamorada

Seahorse Water Adventures

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

Islamorada

Whale Harbor Marina

Whale Harbor Marina — premier full-service marina and charter hub in Islamorada, Florida Keys.

Marathon

Conch Key Fishing Lodge & Marina

Escape to paradise at Conch Key Fishing Lodge—prime fishing, stunning views, and cozy waterfront rooms!

Key West

Captain's Corner Dive Center and Boat Charters

Dive Key West’s stunning reefs and wrecks with expert guides at Captain’s Corner!

Key West

Spencer's Boat Yard

Spencer’s Boatyard & Boat Rentals — Key West’s full-service boatyard for rentals, repairs & marine services

Marathon

Conch Key Cottages

Conch Key Cottages offers charming waterfront accommodations on Conch Key in the Florida Keys. Guests can enjoy private cottages with boat slips, ideal for fishing and exploring nearby attractions.