Vacation rentals in Florida Keys
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top vacation rentals in Florida Keys

Yacht Haven Marina

Cabins at Bonefish Bay

Treasure Harbor

Breezy Palms Resort

Tropical Cottages

Old Wooden Bridge Resort and Marina

Skipjack Resort & Marina

The Hammocks at Marathon

The Islands of Islamorada

Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

Aqua Lodge Rentals At Coconut Cay

Island Bay Resort

Key Largo Cottages

Knight's Key Suites

Anchorage Resort & Yacht Club
When you tell people you’ll be taking your vacation in Florida, it’s hard to say what they’ll imagine. Depending on which part of the state they’ve visited (or if they’ve visited at all), the name might conjure up anything from beachfront high-rise condos to epic Cuban food to giant swamps full of alligators and airboats. If pristine white sand beaches, communities of loveable weirdos, and free-roaming iguanas come to mind, however, you’ll know they’ve been to the Florida Keys. Get to know The Keys like an insider yourself with our Florida Keys vacation rentals.
The Local Life
Yes, it’s certainly different down here in the southeastern-most point of the United States. Will that mean choosing to ride the pedi-taxi with the most bling and loudest boombox blaring Bahamanian Calypso music? Ordering an extra margarita when your favorite Jimmy Buffet song inevitably hits the jukebox in a barefoot bar? Dancing to the beat of your own drum (or to that of an impromptu drum circle)? For Keys locals, it all depends on what day of the week it is.
Your adventures may also depend on which of the 1,700 islands and inlets you decide to explore. Many visitors stick to the sights on the Overseas Highway that connects the largest of the islands, but when you book a vacation rental, the options are endless. Stay at the Pelican Cove Resort & Marina, for example, and ride a bike from island to island along the highway-side pathway—or island-hop the traditional way by climbing aboard a boat and exploring some of the 113 mangrove and sandbar islands that aren’t connected by bridge.
Looking for Florida Keys hotels? When you book a short-term rental with Travelocity instead, you get to travel without feeling like you’ve left home sweet home. That brings a whole new meaning to the term “armchair traveler,” now doesn’t it?
Most popular
- Southern California All Inclusive Resorts & Hotels
- Cheap Hotels in Pocono Mountains
- Northern California Spa Resorts & Hotels
- Northern California Beach Resorts & Hotels
- The Carolinas All Inclusive Resorts & Hotels
- Cheap Hotels in Southern California
- Southern California Hotels with a Lazy River
- Gulf Coast All Inclusive Resorts & Hotels
- Pocono Mountains All Inclusive Resorts & Hotels
- Southeastern United States All Inclusive Resorts & Hotels
- Southeastern United States Casino Resorts & Hotels
- Northern California All Inclusive Resorts & Hotels
- Pocono Mountains Hotels with Hot Tubs
- Pocono Mountains Ski Resorts and Hotels
- Southern California Beach Resorts & Hotels
- Southern California Casino Resorts & Hotels
- Cheap Hotels in North Lake Tahoe
- Cheap Hotels in Gulf Coast
- Ozarks All Inclusive Resorts & Hotels
- Gulf Coast Oceanfront Hotels