Sailboat Rental Florida Keys
Sailing Is What We're All About
Experienced sailors get a 22' Catalina included in their cottage rental, free of charge. We also run an onsite American Sailing Academy school, and larger yachts are available to rent by the hour or day.
We offer roughly 30 square miles of bay-side water to sail, with straight runs of up to 6 nautical miles one way, entirely within the pristine Florida Bay, Everglades National Park, and parts of the Florida Keys National Marine Sanctuary. A thorough chart orientation and boat walk-through are given the morning after arrival.
Sailboat rentals
22' Catalina
Max capacity: 6 people
8 Hours: $300 + tax
Free for guests; non-guests can rent by the 8-hour or overnight block.
25' Catalina
Max capacity: 6 people
8 Hrs $450 · 24 Hrs $575 + tax
Optional captain: $350 (8 hrs) / $450 (24 hrs).
34' Catalina “Ohana”
Max capacity: 6 people
8 Hrs $650 · 24 Hrs $850 + tax
Optional captain: $350 (8 hrs) / $450 (24 hrs).
33' Morgan “High Life”
Max capacity: 6 people
8 Hrs $500 · 24 Hrs $750 + tax
Bay and ocean sailing, sturdy construction.
37' Lagoon “Unforgettable”
Max capacity: 6 people
8 Hrs $750 · 24 Hrs $950 + tax
Catamaran with 2 queen berths forward, full berth aft.
35' Edel “Relentless”
Max capacity: 6 people
8 Hrs $750 · 24 Hrs $950 + tax
Fast catamaran, ideal for weekend getaways.
37' Leopard Power Catamaran
Max capacity: 6 people
8 Hrs $750 · 24 Hrs $950 + tax
Luxury cabins, top deck for sunset cruising.
Call 305-451-7057 to book, or use the online booking engine. Captained charters, sunset cruises, snorkel and kayaking trips are also available through our partner, Morning Star Sailing Charters.
Captained charters & sunset cruises
Sunset cruises, snorkel trips, and private charters through our partner, Morning Star Sailing Charters.
Free boating safety course
Florida law requires anyone born on or after January 1, 1988 operating a vessel of 10+ HP to hold a boater safety ID card. It isn't required for guests using our 22' Catalinas, but we encourage everyone to take the course anyway — it sharpens your boat-safety knowledge.
Skipper’s Society
A low-stress alternative to boat ownership for locals and frequent visitors — no maintenance, insurance, or slip rental to worry about. $599 to start, $125/month, no long-term obligation.