Florida Keys Vacation Rentals

Compare 301 vacation rentals.
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USA > Florida > Florida Keys

Make Florida Keys your next getaway

Escape to island time in the Florida Keys. From Key Largo to Key West, the Florida Keys offer a one-of-a-kind tropical getaway where life moves a little slower, the sunsets are a little brighter, and the ocean is always calling. Whether you’re craving an adventure-filled trip or a serene beachside retreat, our Florida Keys vacation rentals provide the perfect home base for exploring this island paradise.

Explore Florida Keys house rentals, condo rentals, duplexes, and more

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House rentals

View 149 House rentals
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Condo rentals

View 71 Condo rentals
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Duplexes

View 36 Duplexes

Explore more vacation rental amenities in Florida Keys

Pool | Electric vehicle charger | Lake view | Ocean view | Oceanfront | Riverfront | Sound view | Soundfront | Water view | Waterfront

Florida Keys vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Sunrise Suites - Paradise Escape 407
2 Bed | 2 Bath | Sleeps 6

Sunrise Suites - Paradise Escape 407 - Key West, FL

$568 avg / night
4.13 (100)
Passover Cottage
2 Bed | 2 Bath | Sleeps 4

Passover Cottage - Key West, FL

$656 avg / night
4.85 (165)
The Tropical Cove 329
1 Bed | 1 Bath | Sleeps 6

The Tropical Cove 329 - Marathon, FL

$312 avg / night
Sunrise Suites - Saint Croix Suite 212
2 Bed | 2 Bath | Sleeps 6

Sunrise Suites - Saint Croix Suite 212 - Key West, FL

$578 avg / night
4.12 (100)
Old Town Garden Villas - Andros Suite
1 Bed | 1.5 Bath | Sleeps 4

Old Town Garden Villas - Andros Suite - Key West, FL

$526 avg / night
4.74 (133)

View 296 more homes

Recent Florida Keys vacation rental reviews

House is very clean and nicely furnished. Decorated even nicer than the pictures looked. Lots of seating outside, more than in the pictures. Dock was nice, a little hard to get in kayaks from the dock. It’s about a 2 foot drop at high tide. Saw lots of marine life from the back porch even a manatee and a school of dolphins Four nice ocean kayaks and two bikes for use. Bikes were a little rusty, but good enough to get you to the local restaurants. Four nice local restaurants within walking distance, would stay here again.
Michelle P. | Mar 2025
We loved our stay. What we loved the most was the spectacular views and location. The house is very nice and well-equipped. We did wish the pool was heated as the water temperature was cool in February. We had a great time at the house and especially enjoyed watching the parrotfish!
Linda S. | Mar 2025
We had activities throughout the Keys so we chose to stay on Marathon. We had great stay.
Rachel G. | Mar 2025
Florida Keys Frequently Asked Questions

Yes, 111 of our Florida Keys homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 300 of our Florida Keys vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Florida Keys vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Florida Keys team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Florida Keys, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Why vacation in the Florida Keys?

Unbeatable water adventures

Snorkel the only living coral reef in the continental U.S., go deep-sea fishing, or kayak through mangrove tunnels.

Iconic island vibes

Stroll the colorful streets of Key West, sip a rum runner in Islamorada, or enjoy fresh seafood at a dockside restaurant.

Endless sunshine

With warm temps year-round, there’s never a bad time to visit.

World-ramous sunsets

Gather for the nightly sunset celebration at Mallory Square or enjoy a quiet moment on your private balcony.

From oceanfront condos and private homes with docks to luxurious retreats with pools, find your perfect Florida Keys vacation rental with Vacasa.

Does Vacasa offer snowbird or long-term rentals in the Florida Keys?

Live like Ernest Hemingway. Like our weekly rentals, we offer a variety of different snowbird rentals in the Florida Keys to choose from, including beachfront cottages surrounded by palm trees, places to stay near The Key West Butterfly and Nature Conservatory, homes with private pools, pet-friendly rentals in Florida, and so much more.

Florida Keys travel inspiration

The ultimate escape: Key West cottages with private pools Best places to stay in the Florida keys for snorkeling 4 scenic Florida Keys races and marathons for every skill level

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