Vacation rentals in Florida Keys

From Key Largo to Key West, the Keys are a low-key, water-centric escape of stilt cottages, dockside homes, and sunset bars.

Best time to book

December–April for dry, warm weather; May–June and November for better value.

Common 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).

Looking for bookable deals?

Our partner A1 Vacation Homes adds new special offers every week — see what's live across all destinations right now.

Representative homes based on the layouts Florida Keys visitors book most — use them to compare space, amenities, and nightly budget before you book.

Canal-front Home

Islamorada · Florida Keys

3 bd2 baSleeps 8

Boat dockOcean accessKayaks

from $420 / night

Conch House

Key West · Florida Keys

2 bd1 baSleeps 5

Walk to DuvalPrivate patioWi-Fi

from $295 / night

Stilt Home

Marathon · Florida Keys

4 bd2 baSleeps 9

Canal frontPoolGrill

from $365 / night

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.

Neighborhoods, seasons, and booking tips — the full destination guide.