Skip the truck, skip the racks: have a kayak or SUP dropped at your dock in Islamorada and start paddling the Upper Keys flats within minutes. Free delivery, multi-day rental options, and simple safety rules make this a top pick for families and first-time paddlers.
Skip the truck, skip the racks: have a kayak or SUP dropped at your dock in Islamorada and start paddling the Upper Keys flats within minutes. Free delivery, multi-day rental options, and simple safety rules make this a top pick for families and first-time paddlers.
Book with Florida Keys Kayak & Ski
Verified experiences and guided adventures in the surrounding area.
Operated by Florida Keys Kayak & Ski · Islamorada, Florida
easy.
3 days–1 month.
Suitable for people in light to moderate fitness; single outings require basic endurance, multi-day loops benefit from steadier conditioning.
Free delivery covers the off-property boundaries from Tavernier Creek Marina, Mile Marker 91, south to Long Key/Layton, Mile Marker 67; check your booking window for exact drop zones.
Yes—lifejackets must be on vessels during use, and anyone under age 12 must wear one at all times.
No—kayaks and paddleboards should not be on the water half an hour before sunrise or half an hour after sunset to reduce risk.
There is a minimum charge of $500 per piece of lost, stolen, or unusable equipment; follow storage guidance to avoid fees.
Rentals run from a three-day minimum up to one month with tiered pricing for three-day, two-week, three-week, and monthly options.
No—basic paddling ability is recommended, but the equipment provided is stable and suited to first-time paddlers in protected waters.
Indian Key was a small 19th-century maritime settlement; its ruins are now preserved as Indian Key Historic State Park, offering a glimpse of local history accessible by paddle.
The Keys rely on seagrass and coral protection—respect no-anchor zones, avoid trampling beds, and follow leave-no-trace practices to reduce impact.
3 Day - 1 Month Rental Options • For all ages! • Free Delivery

Book with Florida Keys Kayak & Ski