Florida · United States
Cycling in Key West
Best season: December–April (hurricane season runs June–November)
Key West might be the easiest bike destination in America: the whole island is about two miles by four, dead flat, and Old Town’s narrow one-way streets are genuinely faster on two wheels than four. The classic ride is a slow loop through the Old Town historic district — shotgun cottages, Bahamian and Conch-style houses, the Southernmost Point buoy — then along the oceanfront promenade past Smathers Beach. Ambitious riders can point north from Mile 0 onto the Florida Keys Overseas Heritage Trail, the paved route that shadows US-1 up the island chain.
Hotels here lean into bikes. The Kimpton Historic Inns keep small fleets of branded cruisers stationed at each of their five Old Town properties through a partnership with Island Safari Rentals, Southernmost Beach Resort hands out bright yellow cruisers at its concierge desk, and Blue Flamingo sells a package that bundles two bike rentals a day into your stay.
Even if your hotel doesn’t stock bikes, the rental shops will bring one to you: Island Safari, Eaton Bikes, and BikeMan all deliver island-wide (free over a minimum), with basic cruisers from around $10–$20 a day including lock, basket, and helmet. That makes Key West one of the few places you can land without a car and be rolling within the hour.
Practical tip: winter and early spring are the sweet spot — dry, breezy, and busy. Summer is hot and sticky with afternoon storms, and June through November is hurricane season, so shops and hotel programs can pause on short notice. Ride early, drink water, and lock up on Duval Street.
Weather in Key West
Live · NWSLoading current conditions…
Typical by month
avg high/low · 1991–2020 normals · KEY WEST WFO- Jan 75° 63° 2.0"
- Feb 76° 64° 2.0"
- Mar 79° 67° 1.4"
- Apr 83° 71° 2.2"
- May 86° 74° 3.7"
- Jun 88° 77° 4.8"
- Jul 90° 78° 4.5"
- Aug 90° 78° 6.1"
- Sep 88° 77° 8.2"
- Oct 85° 75° 6.0"
- Nov 81° 70° 3.3"
- Dec 77° 66° 2.2"
Bike-friendly hotels
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Blue Flamingo Resort
N Roosevelt Boulevard resort whose bookable Bike Around Key West package includes two bike rentals per day (with basket, helmet, light, and lock) through a partnership with Fury Water Adventures; book 5 days ahead.
Before you book: Confirm the package price premium over the standard rate, whether non-package guests can rent bikes, and if the 5-day advance booking rule still applies.
Bike program verified via source (2026-07-11)
Kimpton Key West — Historic Inns Collection
Five Old Town Kimpton inns with a formal Island Safari Rentals partnership: 4–8 branded cruisers stationed at each property, every rental including helmet, lights, basket, and lock, reservable at the front desk with delivery in 15–30 minutes.
Before you book: Confirm current rental pricing through Island Safari, whether on-property fleets can be reserved before arrival, and e-bike availability per inn.
Bike program verified via source (2026-07-11)
Southernmost Beach Resort
Oceanside Old Town resort that rents its signature bright yellow cruiser bikes — basket, lock, and helmet included — from the concierge desk, steps from Duval Street and the Southernmost Point.
Before you book: Confirm the daily rental price (not published), whether bikes are reservable in advance, and any waiver or age requirements.
Bike program verified via source (2026-07-11)
Where to rent or borrow a bike
BikeMan Bike Rental Key West
From $10/day
Budget cruiser specialist — $10/day multi-day or $65/week with locks, helmets, baskets, bells, and lights included free; free hotel delivery and pickup on rentals over $60 plus 9–5 roadside assistance.
Call ahead: Confirm single-day (non-multi-day) pricing and waiver requirements.
Verified via source (2026-07-11)
Eaton Bikes
Rates by phone
Full-service shop at 830 Eaton Street (second location on Truman Ave) with Sun cruisers, tandems, trikes, Trek road/hybrid bikes, kids' bikes, and Burley trailers; free contact-free delivery island-wide for online reservations.
Call ahead: Confirm current rates (rate sheet not published on the main page) and waiver requirements.
Verified via source (2026-07-11)
Island Safari Rentals
From $20/day
Old Town shop at 424 Greene Street (two blocks from the cruise terminal) with adult cruisers from $20/day, kids' bikes, tandems, and trailers — locks and baskets included, free delivery and pickup from any Key West hotel; official bike partner of the Kimpton Historic Inns.
Call ahead: Confirm shop hours and waiver requirements.
Verified via source (2026-07-11)
We Cycle
Rates by phone
Local Key West bike shop offering rentals; the site blocked automated verification (HTTP 403), so rates, address, and fleet details need a manual check.
Call ahead: Confirm the shop's address, hours, rental rates, and what's included — site could not be loaded during research.
Reported via source (2026-07-11)
Cloud of Goods (Key West delivery rentals)
From $50/day
Delivery bike-rental marketplace — hybrids and cruisers (~$50/day) and mountain bikes (~$70/day), helmet and lock included, dropped at your Key West-area hotel, rental, or the airport. No storefront; you pick the delivery spot.
Call ahead: Confirm the city page link, current fleet, delivery area, and rates for your dates.
Reported via source (2026-07-14)
Guided bike tours
Lloyd's Tropical Bike Tour
Lloyd's Tropical Bike Tour · 2.5h · from $69
The classic Key West ride — a leisurely 2.5-hour guided cruise through the historic neighborhoods with tropical fruit tastings, Conch-house architecture, and botanical-garden stops; daily at 9:30am from 428 Catherine Street, bike included.
Where these are on the map Key West
Hotels Rentals & loaners · 6 of this destination's listings located · © OpenStreetMap contributors