Canal-front HomeIslamorada Dock House
Islamorada · Florida Keys
3 bd2 baSleeps 8
Boat dockOcean accessKayaks
from $420 / night
Florida
Florida Keys vacation rentals
A string of tropical islands connected by one legendary highway.
Best time to visit
December–April for dry, warm weather; May–June and November for better value.
Rental types
Canal-front homes with docks · Stilt cottages · Resort condos · Key West conch houses
Getting there
Drive the Overseas Highway (US-1) from Miami or Fort Lauderdale; Key West has an airport (EYW).
Why the Keys work as a rental trip
The Keys are narrow, laid-back, and built around the water. A rental with a dock or beach gear puts you in the middle of the action — fishing, kayaking, and sunset cocktails without fighting traffic every day.
Key West is the only truly walkable town; everywhere else you'll want a car. That's why many travelers split their trip: a few days in the Upper or Middle Keys for water sports, then Key West for nightlife and history.
Things to do
- Snorkel or dive the reefs of Key Largo Dry Rocks and John Pennekamp
- Feed tarpon at Robbie's Marina in Islamorada
- Kayak through the mangroves of the Florida Keys National Marine Sanctuary
- Watch the sunset at Mallory Square in Key West
- Visit the Hemingway Home and the Southernmost Point
- Fish for mahi-mahi, tarpon, and bonefish on a charter
Booking tips for the Florida Keys
Waterfront is the premium here, but not all waterfront is equal. A canal home with ocean access and a dock is ideal for boaters; a stilt cottage on a busy road may feel less private. Ask about hurricane-recovery status and dock availability.
- Confirm whether a boat dock is included and how deep the canal is
- Hurricane season runs June–November; check cancellation policies
- Key West has strict short-term rental rules — verify the property is licensed
- Book winter months far ahead; summer offers the best rates
Where to stay in Florida Keys
Key Largo
The first island — dive shops, mangrove bays, and easy access from Miami.
Islamorada
The sportfishing capital, with upscale canal homes and sandbar culture.
Marathon
A family-friendly middle Keys base with beaches and turtle hospitals.
Big Pine & Lower Keys
Quieter, more natural, and home to the tiny Key deer.
Key West
The southernmost city — walkable, historic, and famous for sunsets at Mallory Square.
Example rentals in Florida Keys
Browse all Florida Keys rentalsCanal-front HomeConch HouseKey West Conch Cottage
Key West · Florida Keys
2 bd1 baSleeps 5
Walk to DuvalPrivate patioWi-Fi
from $295 / night
Stilt HomeMarathon Family Retreat
Marathon · Florida Keys
4 bd2 baSleeps 9
Canal frontPoolGrill
from $365 / night
Florida Keys FAQs
How long does it take to drive the Keys?
From Key Largo to Key West is about 3.5 hours without stops. Plan a full day if you want to explore the islands along the way.
Is the water clear everywhere?
The clearest water is on the Atlantic side and around the reefs. Florida Bay can be murkier but is great for kayaking and fishing.
Can I bring a boat?
Yes — if your rental has a dock with ocean access. Ask about tide, depth, and bridge clearance before trailering down.
Which Key is best for families?
Marathon and Islamorada offer calm beaches, family restaurants, and easy access to both water sports and Key West day trips.
Keep planning
Travel guideFlorida Keys Road Trip: From Key Largo to Key West
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